At the time, more than a million users at nearly 500 companies around the world were using Lessonly’s software.

Yoder wanted to reach 10 million more.

To do so, Lessonly needed to grow its sales team. But the company had already reached a point where it was getting more and more difficult to effectively train its account executives. With nearly 50 employees, the once-lean startup could no longer rely on a “buddy-system” training program that allowed sales reps to learn by watching.

In its early days, Lessonly had trouble measuring ramp, or how long it took for its new account executives to become productive sales reps. By the time Naas came aboard, the company’s ramp time was scattershot. Some reps would learn faster than others, but the results were inconsistent. For some, it took just a few weeks to grasp the best practices around their role and hit their quota. For others, it was taking as long as a year for them to make their number. They needed consistency.

So, Naas and the rest of the sales and marketing leadership team set out to create what would essentially become an incubation program—a trial-and-error system that saw them test a range of onboarding ideas in search of the best practices that they could sell to their customers.

Then, a funny thing started to happen. As Naas and Lessonly settled on the structures, processes and measurables that they hoped could benefit their customers’ sales teams, the company’s own ramp time began to improve. Within a year, it had dropped 40%.

“We’d gotten to a point where it was too difficult for us to share what’s working well, as the team grew,” he says. “The best practices and tribal knowledge was growing so much that we had to rein it in and start putting a process behind it. And that's exactly what we want to help our customers do. We recognized it was time for us to do it internally, as well.”

The first thing the company set out to do was identify the key metrics that would serve as the basis for their ongoing evaluations of new sales reps. They settled on 10 specific data points which were broken down into five objective and five subjective KPIs.

Objective KPIs:

1. Self-sourced opportunities
2. Pipeline
3. Win rate
4. Average contract value
5. Quota attainment

Subjective KPIs:

1. Grasp of role
2. Conveying value
3. Navigating process
4. Meaningful sales conversation
5. Confidence in success

The metrics would give the sales team the opportunity to document each rep’s entire onboarding process, allowing both management and rep to track their performance in real time. But while the objective metrics could be quantified with raw numbers, the subjective goals were more personalized and required sales managers to use their own intuition when evaluating performance.

The gut-check comes each month in the form of a survey Naas gives to every manager who then sits down and asks the individual reps a series of questions about their performance over the previous 30 days.

Managers use those answers to determine whether or not they think an individual rep is able to navigate the sales process and interact with customers and prospects the way the company wants them to. Taking each new rep’s unique situation into account allows Naas and the sales managers to look beyond the raw data to see how the person might project over time.

For their part, the managers are trained on how to interpret the reps’ answers to the survey questions and assign a one-through-five-star rating for each. If a sales rep isn’t hitting their objective numbers but scores well on the subjective assessment, the company considers other reasons to explain the individual’s troubles.

“The managers decide ‘do I think they can be successful, even if they’re not successful right now?’” Naas says. “There are situations where we still want to invest in that individual because we’re seeing the non-tangible things that they are exhibiting.”

Lessonly records the information it gathers and fills out a monthly scorecard for its new reps. Each individual is ranked based on their “data score,” which combines the objective KPIs, and a “person score,” which is the total score on the subjective measures:

Sales managers use the two numbers to rank the reps and each person’s score is plotted onto a quadrant that is used throughout the onboarding process as a visual to track their overall progress:

“We knew we needed the managers to have a role in this measurement process, but we needed to be able to quantify [the objective and the subjective],” says Naas. “This way, we could bring the two things together.”

When the circumstances allow, Lessonly likes to hire its AEs in cohorts. They might hold back or speed up start dates in order to bring in an entire “class” of new reps at the same time. But very little learning is done in a classroom setting. Naas estimates each new group of reps probably spends between four to six hours—and rarely more than 30 minutes at a time—in a classroom.

The company prefers to use its own virtual-training products while employing a social-learning strategy that allows the reps-in-training to feed off of each other over the course of the program. So in addition to onboarding their newcomers with the very products they will soon be selling to customers, Lessonly believes in letting trainees learn by doing. And it starts on day one.

CEO Max Yoder has long pushed the idea of “sharing before you’re ready.” In his recent book, Do Better Work, he says he urges all of his employees to “be vulnerable,” and allow themselves to fail and learn from those mistakes. Naas says that idea is the cornerstone of the company’s onboarding program. Within the first few hours of their first day on the job, new reps begin preparing for real-life interactions with customers—whether they’re ready or not.

Those first attempts are notoriously nerve-wracking for the reps themselves. But Brett Johnson, who joined the company in February, says fumbling through that first mock-call just hours into his first day at Lessonly was the most important bit of training he received.

“It was a struggle, that’s for sure,” he says.

Naas says too many companies fail to emphasize the importance of practice. Most companies put their new reps through a weeklong bootcamp, overloading them with slide decks, and quick tutorials on the products and services they’ll be selling. Almost immediately, they’re put directly in front of customers. The best new reps will succeed in spite of that sort of drive-by training method, but most others require more hands-on learning that emphasizes trial and error in a safer environment.

In today’s climate that sees sales roles go unfilled for months, with little experienced talent to go around, leaders must invest to turn B players into ‘A’s, and practice helps close the gap—which increases results of the majority of reps, even those who are not rock-stars on day one.

Lessonly’s emphasis on practice empowers its new reps to fail early on without the pressure of blowing a possible deal. “You have to try things,” says Naas. “You have to say the words to get it right—share before you’re ready. You’re going to make mistakes, and that’s part of the process. But now when you do get in front of your customer or prospect for the first time, you’re going to be as buttoned-up and polished as possible. It’s amazing to me how many companies ignore the importance of practicing."

Lessonly’s onboarding program lasts seven months. It’s a front-loaded process, divided into five phases, beginning with an intensive, two-week experience in which each hour of the day is accounted for:

Naas says the company designs each phase to give more autonomy to the sales rep. As they move through the process, the rep is given more responsibility and becomes accountable for hitting goals. By phase five, reps are expected to have learned what they need to know to perform the duties of a full-time account executive, but are still monitored for coaching opportunities:

The first two months are very intensive with the goal being for each AE to close their first deal in 60 days. In the first week, the company combines its practical and virtual learning tools with more traditional shadowing activities, allowing new hires to watch the company’s best reps in action.

By the end of their second week, the new reps will have spent much more time practicing with their peers and observing veteran AEs than they have sitting through lectures or wading through binders of rote training materials. They’ll have drafted their first email pitches aimed at different buyer personas, drilled with their managers on responses to common objections and role-played entire cold calls.

When it comes time to make their first live calls, the new hires are reaching out to prospects they’ve found themselves—they’re not given company-generated leads from the start.

“They have to earn that,” says Naas.

But by forcing their new hires to generate their own leads, sales managers are able to look at more than just sales wins when evaluating their performance. Before they ever get on the phone, reps are introduced to tools like DataBox, SalesLoft and Sales Navigator and are taught how to mine them and narrow down potential prospects. Johnson says he struggled with prospecting early on and that having access to the more veteran AEs was invaluable.

Once the first two months are complete, Naas says the company begins to pull back and slowly grant more and more personal responsibility to the new reps. The scorecard still gets filled out and charted, and the AEs still learn from their veteran peers, but by months five, six and seven, the onboarding process is nearly complete and reps are spending the lion’s share of their time with their teams.

“Too many companies just cut off the onboarding process and say ‘go do your job,’” Naas says. “We phase it out over time because there’s still learning that needs to happen, even once you’ve started to become productive. The ramp is what we’re trying to shorten. I never want to shorten onboarding.”

It was well after midnight and he was trying to put together the perfect cold email template. The next morning he would be launching KlientBoost, his second PPC agency in almost as many years. His first, Disruptive Advertising, which he co-founded with a partner in Provo, Utah, had grown from launch to $2 million in annual revenue in just under 18 months.

But while lying in bed on that March night in 2015, he was starting from scratch, again. He had no customers, no office and no real leads. He had decided to start out with a cold-email strategy, but still had yet to decide on his approach.

“I was frantically e-mailing myself tidbits and snippets,” he says. “I wanted to have my template points ready to go the next day.”

That first round of emails would yield his first three customers. A year later, KlientBoost would boast $1.2 million ARR. Four years later, the company has grown to 60 employees and it recently hit $700,000 MRR. To Dane, it all came from that first email.

“We come with a focus on helping people make more money,” he says. “That was the context of that email and it’s the same principle for how we’ve grown to the size we are now.”

The initial strategy was to fire off as many cold emails as he could. But the first order of business was figuring out where to send them. Before he’d even written his template, Dane set out to determine who his target companies would be. As a pay-per-click agency, he decided he’d have more success reaching out to companies with larger advertising budgets.

He used website analytics tools to help pinpoint his ideal companies, then he set out to find some hard targets. Using platforms like SpyFu, Moz and Ahrefs, he was able to find companies that were both close enough that he could meet with them face to face and large enough that they had monthly advertising budgets of more than $10,000.

Next, he needed email addresses.

Dane hired an India-based temp through Freelancer.com, for $4 an hour and built a specific, step-by-step routine for his new employee to follow. Rather than write out the steps and hope nothing would get lost in translation, he instead signed up for a free trial with Screencast and recorded a 60-minute onboarding video that explained, down to the detail, exactly what he was looking for. He posted the video on YouTube and sent his employee the link.

“If I would’ve written out the job details word for word, then I’d probably be wasting more time and getting more headaches trying to communicate something that someone else would interpret differently,” Dane wrote in post on the KlientBoost blog. “The visuals within the video and the ability to pause and come back to certain steps definitely [helped the freelancer] get the job right the first time.”

Using the WHOIS database, which is a listing of all registered online domains, the freelancer surfaced about 750 relevant, personal email addresses. Those addresses cost Dane about $0.38 each.

In his first month, Dane estimates he sent “maybe 100” cold emails to companies he’d researched, but with whom he’d had no previous connection. Only he wasn’t pitching them on his company. His initial approach was to come in like a pro-bono consultant, offering an immediate and unsolicited critique on how he thought a company could improve their conversion rates. Each email was personalized.

“I used a template, but I put in a lot of research for every single e-mail,” he says—and he didn’t mince words.

Almost immediately, the responses started coming in. Some weren’t interested. Others challenged his critiques of their business. But very few people told him to get lost and many were interested enough to engage:

All told, the cold-email strategy quickly earned KlientBoost its first three customers. Within three weeks, Dane says the company had signed them up to contracts, each worth about $2,500. He’d put a lot of work into finding the businesses he should be pitching and the right people to reach at each one. But the key was that he was offering them more than just his product.

“We wanted to help them,” he says. “You dangle the carrot and tell them ‘I have plenty of experience from other companies taking advantage of these ideas and if you take advantage of them, you’ll see an improvement in your performance.’ That first email was an attempt to get a reply, but it also signaled there was something in it for them, too.”

The cold email strategy could only last so long by itself. With his first customers in the bag, Dane shifted gears again. He knew the cold email strategy was unsustainable, so he leveraged his experience with Disruptive and KlientBoost’s earliest clients and turned his attention to building his own brand through content and thought leadership.

In the early days of Disruptive, he remembers thinking the company should have been doing more to build a brand and establishing itself as recognized thought leaders in the PPC and CRO landscape. It was one of the main drivers in his decision to branch out on his own. KlientBoost was his chance to lead with brand front and center.

The next step was putting together a content marketing program, which Dane says is what took him from an unscalable strategy of cold-emailing to more than $100,000 ARR over the next 11 months.

At first, he employed a largely ineffective post-when-you-can strategy. Dane says he was writing “when I had the time,” both on the KlientBoost blog and in guest posts elsewhere. When he got too busy, he began paying writers $300 a post to feed the content machine.

Those early posts, he says, were strong, but he was having a hard time generating organic traffic.

The new plan was simple: post more, probe more, pay more, promote more.

He increased his content budget from $300 to $600 per post, but he asked his writers to go more in-depth. “I wanted more examples, more statistics, more proof, more takeaways,” he says. Meanwhile, he began to force himself to write more on his own site and hired two new employees to work only on promoting KlientBoost’s content and improving SEO.

Dane says it dawned on him around this time that the only way the company was going to grow was by focusing on content.

Throughout most of that first year, he says most of his new customers came from his guest blogs posted on other sites (“piggybacking,” he calls it). “I would leverage the main authority of the company that had already built an audience that was similar in interest to what I was going to write about,” he says. “It was the fastest way we were able to get our own blog off the ground.”

He was able to call on his previous success with cold-emails to get his work published on blogs he identified as relevant to KlientBoost’s audience. He made what he calls a “hit list” of blogs he wanted to write for and would link back to other successful guest posts he’d written “as bait for them to say yes.”

The guest posts led to invites to appear on podcasts which led to webinars which led speaking engagements, which by the end of KlientBoost’s first year had become one of the company’s biggest driver of new business.

In essence, Dane was once again relying on thought-leadership and educating his customers to help drive new business.

“Literally all of our growth is from our blog,” he says. “And our content is all focused on scratching backs and giving value. What can I see that are some clear things that [other companies] might be missing? Eventually, we’d get people knocking on our door. They'd read the piece of content or listened to something or just consumed something that gave them value and a little bit of trust would have already been built.”

Dane has never stopped looking to build trust and give value to KlientBoost’s still-growing customer base. While the company has outgrown its humble, solo-cold-email beginnings, the idea of giving away free advice to prospects is still a centerpiece of its sales strategy.

KlientBoost’s initial discovery calls with any prospective client immediately becomes a more hands-on version of those early pro-bono consulting sessions. While KlientBoost determines whether or not the prospective customer is a fit, the company is getting an in-depth tutorial on what their advertising strategy should be—whether they choose to work together or not.

Dane says he asks for access to each company’s GoogleAds accounts and conducts what he calls an “opportunity screen-share,” in which the customer shares its goals. KlientBoost creates a 10-point action plan based on those goals. If the company decides to sign a contract, KlientBoost executes the plan. If not, the plan is still theirs to execute or not.

“We want them to say, ‘You guys do this all the time, so your execution is going to be much better than ours,’” Dane says. “It’s the same premise we’ve had from the beginning, going all the way back to those first emails or those first guest blog posts. It’s just an evolution of what we’ve always done—putting our money where our mouth is.”

But when he got to Austin, everything came to a halt.

Frustrated that he wasn’t able to grow his new territory as fast as he was used to, he came up with a simple question: “How are you sold?” At every meeting, he would ask sales leaders he met with to explain what moved them to make a purchase. More often than not, he got some variation of the same answer: “Creativity.”

He used that common refrain to develop a targeted, personalized gifting strategy that helped him build more than $700,000 in pipeline and close $147,000 in sales in just three months. All it took was a small investment of his own money, some focused research—and a lot of coffee.

InsideSales has always pushed its reps to personalize their messages to buyers whenever possible—and the idea of giving gifts was nothing new to the Salt Lake City, Utah-based firm. VP of Marketing & Sales Development, Gabe Larsen, became an advocate for branded gifts and personalized messaging while working in enterprise sales at Gallup Consulting.

When the company found itself going after big accounts in the early 2010s, Larsen came up with a list of 50 target companies and started a traditional cold outreach strategy of emails and phone calls. Coca-Cola was one company he remembers being particularly hard to break into.

“I was having zero success and hadn’t been able to get a meeting with them,” Larsen explained during a 2017 webinar. He and a colleague sat in a room and brainstormed a way to grab the global soft-drink conglomerate’s attention. He came up with an idea to put together a gift box of all of Gallup’s most recently published books on management and corporate strategy. He got each book signed by the authors, put the company’s logo on the outside, and packaged them together with a small, handwritten note.

“Wouldn’t you know it, we got a meeting,” Larsen said. “I remember thinking, ‘Oh my goodness, we’re on to something, here!’”

By the time he joined InsideSales in 2013 as head of strategic sales consulting, he’d developed a gifting strategy and began implementing it at his new company. They called each campaign a “play,” and sometimes sunk thousands of dollars up front in order to generate millions in pipeline.

Those “plays” demonstrated what Larsen describes as the difference between account-based marketing and account-based sales. “Marketers will run a big campaign, it will take them six months to create, they’ll send it to a thousand prospects and hope to hear back from them,” he says.

“You don’t always have to lean on marketing’s shoulder to be able to do these kinds of campaigns. You drive it. You come up with the idea. You find the select group of companies you’re going after. You tell the BDRs and the SDRs what to do. You can run it yourself, and you can make money.”

But it wasn’t until Joey Wood’s coffee play that he realized just how effective a small-scale, surgical-strike campaign could be.

For Wood, the first order of business was deciding what his gift should be. Given that he was just starting out in the Longhorn State, he wanted to find something that would appeal his buyers’ sense of local pride. In other words, the gift needed to have a Texas theme.

Wood knew he wanted the campaign to revolve around coffee—he’d already decided to give each contact a $10 Starbucks gift card—and he had just learned that Yeti, the popular high-performance cooler and drinkware manufacturer, was based in Austin. He selected a $30 coffee tumbler and had them branded with the InsideSales.com logo. In order to find out how many mugs to order—and, ultimately, what his initial cash outlay would be—Wood next set out to identify his targets.

Using what Larsen calls “a combination of art and science,” Wood started researching which accounts best fit his particular campaign.

Then he began a qualification process to figure out which new accounts he should target.

InsideSales uses its own scale, called ANUM, when it comes to qualifying the accounts and individual contacts its sales reps target. Using this framework, they determine who at a company would have to purchase Authority, which company would have the Need, who would know the level of Urgency the company might have to buy, and how much Money the account would likely have to spend.

Wood used a 3-2-1 scoring system to narrow down his list of accounts by the types of sales tools and technology they used and the amount of money they would likely be able to spend. Companies that used larger CRMs like Salesforce and Microsoft Dynamics were scored as 3 and 2, respectively. Likewise, VC-backed companies were scored a 3 as they would be most likely to have a larger budget for new resources. Public companies were scored a 2 and private firms a 1.

Wood ended up with a list of 10 target companies. Then, using LinkedIn, he researched who at each of those companies would typically be involved in the buying cycle. Using VP of Sales as the baseline, Wood identified three to five contacts at each of the 10 companies.

His list was complete—he would need 42 Yeti mugs and $420 in Starbucks cards.

“One thing Joey nailed was finding a gift local to those accounts,” Larsen says. “His territory was Texas and those Yeti mugs come from Texas. He found something that would resonate with people in his region. He doubled down and said, ‘What’s a gift local to them that really kicks butt?’ He got creative.”

With his list of 42 names, Wood’s next step was to research every name and find out as much as he could about each one in order to personalize his handwritten note. “We researched the heck out of them,” Wood said during Larsen’s webinar. “We used LinkedIn, Twitter, our own internal tools—anything we could use to gather insights. We used our own predictive science to figure out if we were to get this person’s time, would they actually buy from us? So there was a lot of prework done beforehand.”

When it came time to send out the packages, the gift box looked like this: the Yeti mug, the Starbucks gift card, the personalized, handwritten note, and Wood’s business card.

Wood says the handwritten note might have been the secret weapon in the campaign’s success.

Even once the packages had landed, Wood’s work was far from over. He drew up a 10-touch cadence that his business development team carried out. The day after a target received their package, they would get a phone call or voicemail, along with an email.

The next day, they would receive a second call or voicemail, this time accompanied by a text. The third day brought another call and another email, followed by one more email on the fourth day. On the fifth day, if Wood still hadn’t heard back from the contact, they would receive a private message on LinkedIn. Only if there was still no response after the LinkedIn message would Wood give up.

“If you’re not going to respond to me after 10 tries, enjoy the free gift,” Wood says.

But once the packages went out, that was not a problem he encountered much.

Within a month of sending out those 42 Yeti mugs, he had landed 18 meetings—a 43% success rate.

Between the Starbucks gift cards, the Yeti mugs, the branding, and the delivery charges, Wood’s coffee campaign cost him upwards of $4,000—for which the company would eventually reimburse him.

Companies that close large enterprise deals can afford to take the risk on such an aggressive sales play. But Larsen says smaller companies shouldn’t hesitate in tweaking a campaign like the coffee play to fit into their budget.

The handwritten cards were the cheapest component of Wood’s gift package—about $200 total—and both he and Larsen believe they had the most impact.

“Handwritten cards are a game changer,” he says. “And if you’re a company that is doing more transactional sales, working with smaller-sized deals, you don’t have to send a branded mug, you don’t have to send a $10 coffee card. And your gift doesn’t have to be expensive—it can be a plate of donuts or brownies. But start with the handwritten note that costs you fifty cents to send. You wouldn’t believe how powerful that can be.”

It was a particularly sweet victory for then-director of sales, Tonni Bennett, who had almost single-handedly dragged the company over the finish line.

Bennett joined Terminus as its second sales employee, but didn’t have time to think about building a team around her. As the company’s ninth employee and first dedicated sales leader, her initial directive was pretty simple—she had to sell.

At the time, Terminus was just a few months old and the sales team consisted of Bennett and one account executive who had started just days before her. They had only a handful of customers, all of whom were brought in by the founders and the company was still tweaking its ideal account fit.

Bennett was responsible for developing the company’s sales process and crafting all of its messaging, but she also met with prospective customers, demoed Terminus’ account-based marketing platform more times than she could remember—and, most importantly, closed sales. When they hit that magic $1 million number nine months into her tenure there, she resisted the temptation to celebrate too hard, because, in a way, her work was just beginning.

“That first year was extremely challenging,” says Bennett, now a consultant with Skaled and her own firm, T&L Bennett, which she runs in Atlanta with her husband.

“We managed to cover a lot of ground in terms of sales and it was really just the two of us. But it doesn’t get any easier after you hit $1 million. Not only do you have to keep building and replicate what you just did, but you have to give up some of that control and start letting other people do it for you.”

In other words, staring into 2016, Bennett had another gigantic mountain to climb. She had to build the company’s first sales team.

For Bennett to understand exactly how she should go about scaling her sales team, she first had to consider why Terminus hired her in the first place. She was just 27 at the time she joined the company and had spent the previous three years as a senior account executive with Pardot and SalesLoft—two companies that sold marketing automation software.

Given that Terminus sold account-based marketing, Bennett was a natural fit to join the team. The more nuanced decision was asking her to lead it.

“I’d never led a sales team,” Bennett says. “I’d never hired anybody. I’d never fired anybody. I’d never built a sales operation from the ground up—but that’s what I was being hired to do.”

“I worked out,” she says, with a laugh. “But it’s funny—the smartest thing they did was not specifically hiring me personally, but someone like me. Startups shouldn’t be looking for some executive who makes $300,000 for IBM, as that is the wrong DNA. First of all, that person probably wouldn’t want the job. You need someone who is scrappy, eager to prove themselves, and can continue to grow in the role. I always joked that they were lucky with me because neither the CEO nor I knew I was capable of doing that job until I was in it.”

Bennett says she was never given a specific number of account executives or sales-development reps to hire. Instead, she concentrated on building a pipeline of potential candidates by finding the online communities where prospects interested in tech and startups would spend their time. In Atlanta, that meant the job boards on startup news site Hypepotamus, the Atlanta Tech Village’s website and Georgia Tech University’s startup incubator, ATDC.

Bennett also spent hours poring over LinkedIn profiles, sourcing what she had established as her ideal sales rep profile. At first, she looked for seasoned reps with between three and five years experience, preferably with experience selling marketing technology.

“As I hired the first members of my team I had to come to them and say, ‘Look, I’m not going to have all the answers. I’m going to mess some things up—we’re all figuring this out together.’ Including your team like that when you’re a small, early-stage company can be really useful, too. I got a lot of great ideas from those more veteran hires that made me look very smart.”

Bennett also started making a note of which companies tended to have the most employees that fit her profile for Terminus and used LinkedIn to drill deeper into their sales teams looking for potential candidates. After developing a list of 10-12 candidates who fit the preferred profile, she began the process of reaching out and suggesting a meeting. The first touches, she says, were short, casual notes—usually via email —asking for a short phone conversation.

Those notes would often begin with:

After this brief introduction, she’d get right to the point. “We’re looking for some entrepreneurial reps who we think could help establish the culture of our growing team. We don’t know each other very well yet, but you look like you might have what we’re looking for. Would you be open for a chat?”

Bennett says it’s important, in those first calls, to use some phrases that would pique the interest of “the right kind of candidates.” She could tell simply from a candidate’s LinkedIn profile if they had the tangible experience she was looking for. But not everyone views being part of an unknown startup and helping build a sales culture as a big enough carrot.

“I looked for their reaction to those kinds of things,” she says. “The ones who got excited by the idea of building something were the ones I wanted to talk to. I got a really good response from that approach.”

Early on, Terminus CEO and co-founder, Eric Spett, would conduct the first phone screens with new sales candidates, but Bennett found that too many candidates were able to pass that initial round with flying colors only to fall flat in subsequent rounds.

It’s a problem she says startups often run into when non-sales people—often company founders—are tasked with evaluating sales candidates. Simply put: too many sales people are better at selling themselves than they are at selling your product.

As the team began to scale, Bennett started handling the first conversations, and before even bringing a candidate in for a face-to-face interview, she tried to get to the heart of what kind of role they had in their current position, which part of the sales funnel they'd touched, and which stage of the customer journey they covered.

Did their role center mostly around prospecting or were they upselling existing customers? Were they running the full cycle? What were the metrics they were responsible for?

The second conversation was an in-person interview. During that first face-to-face meeting, Bennett looked to size up the candidates for the intangible qualities she wanted members of her sales team to possess. She came up with four traits that she thought all top-performing sales reps had in common:

• Communication skills — “This wasn’t just ‘can you speak well?’; this was 'are you able to talk to our customers the way they like to be spoken to?” Bennett says. “Can you get out of the corporate-speak and be friendly and engaging? Can you describe our product in a way that doesn’t sound like you’re reading from a textbook?”
• Hustle — ”When we were a startup, we weren’t the kind of company that was going to give you 100 different accounts to farm. We needed someone who could prospect on their own, understand who we were targeting, and take the initiative to find the right fits.”
• Coachability — “You have to be able to take feedback. There are a lot of moving parts when you’re a startup, and, especially in tech, the market is always changing. You have to be able to handle criticism, and you also have to be willing to learn things quickly.”
• Adaptability — “This builds on the coachability component—how fast can you pick up on a new concept and put it into play? Our reps who could take a new talk track and apply it the next day were the ones who would always see success the fastest.”

The candidates who were able to impress during the first in-person interview were then brought in for the final and, Bennett says, most important step in the hiring process. Learning to like a candidate personally was the easiest part of the journey. The key was finding out if they could sell. More specifically—could they sell Terminus?

The final step was asking candidates to sell Terminus and its product to Bennett and the company’s executive team. First, the candidate would shadow the sales team for a day to familiarize themselves as best they could with the product, sales cadences, and talk tracks. Then they’d get a couple of days to create their own business plan before returning to pitch Terminus to Terminus. That final process was often the clincher.

In the 12 months after Terminus reached its first $1 million in revenue, Bennett grew the sales team from two to 10. The company jumped to $5 million in revenue during that same time. As the company grew, she started to tweak her ideal candidate profile, shifting away from veteran sales reps in favor of younger, early-career professionals, largely because it had become easier to onboard new sales employees.

That wasn’t the case when those first hires joined the team the previous year.

When she hired her first sales rep, Bennett was also in the process of building Terminus’ entire sales program. Between figuring out how to demo the product to prospects and creating the company’s go-to-market strategy, she started to realize that it would be impossible to devote the time necessary to train additional reps as the team scaled. So she enlisted the help of the one rep she had already hired to create a training program for subsequent hires.

“Since I was training him live, I told him he needed to take really good notes and I had him share them with me,” she says. “Then I’d take about 15-30 minutes at the end of each day and I’d organize those notes into a document. By the time we hired our next person, we had this primitive document already and it was very helpful. Then I told that hire to take more notes and I’d add those to the original document. It became a living thing that we could add to as we went. We used a version of that first set of notes for years.”

The final piece of the puzzle was figuring out the metrics to which her sales reps would be held. That presented a real challenge early on because the only baseline she had was the sales work she and her one rep had done in their first nine months. Bennett says there was little science to how she came up with the numbers she wanted her team to hit—she made them up.

“I made them a promise,” she says. “I told them I was literally going make a goal for them out of thin air. I had no real data yet to make that goal, but I told them that if I realized it was too high, I’d lower it. If it was too low, I’d raise it. And if they committed to work their asses off to make the company successful, we would make sure they were well compensated. They trusted that I meant it, and that set them—and us—up for success.”

For business development reps, she set their goal at setting and completing 16 qualified meetings per month. Her account representatives were given prorated revenue goals based on their experience. But for all members of the team, she made it clear that she would not be holding them to more granular activity metrics like total number of dials or talk time.

She remembered her work as a young inside sales rep for United Parcel Service when she was held to more than two hours of phone time a day. Arbitrary measures like that are easy to exploit to no benefit for the company.

"I think when you tell people ‘these are the activities that will get you to your number, all of our top performers are hitting them and I highly recommend you do it, too,’ they get the picture. But if they can find another way that’s just as good and they’re hitting the goals that matter, that’s fine too.”

By the time Bennett left Terminus in December 2018, she had been building the team for just over two years. During that time, the company grew to more than $10 million in revenue, and Bennett had put together a team of more than 50 account executives, BDRs, and sales managers. From the beginning, Bennett says her singular goal was minimizing mistakes when it came to hiring.

“Bad hires are expensive and time-consuming,” she says. “We needed to perfect our process very quickly because as a growing company, we didn’t have a lot of time or money to be able to absorb too many of those. We built a really strong team and, looking back on my time at Terminus, that’s one of the things I’m most proud of.”

But in the back of Fraser’s mind, there was a nagging voice saying, “That was too easy. They would have paid more.” And when he thought about it, the little voice was right. Fraser’s new client hadn’t quibbled on cost or service. They’d agreed to the list price on the first call and had paid immediately with a credit card. It was all too easy.

The more he thought about it, Fraser realized he had experienced this quite a bit at his company, SaaSquatch. A customer would get in touch, learn about his product, and convert almost immediately—and that didn’t sit right with Fraser.

With his sales team still celebrating in the background, Fraser decided to claw back some of his lost revenue. Over the next year, Fraser would take the dramatic step of increasing his pricing by 100 percent—all without losing a single lead.

In March, 2013, Fraser had launched his first company, a simple customer referral platform called Referral SaaSquatch. It helped small businesses create and manage refer-a-friend programs. Fraser priced the platform as a low-to-mid-tier option and it quickly gained traction among small- and medium-sized businesses.

Within two years, Fraser had signed up a bunch of clients and hired Referral SaaSquatch’s first dedicated employees. Eventually, though, the company hit a natural plateau and Fraser began looking for new opportunities. And in the winter of 2017, he found one.

In May, 2018, Fraser launched his second company, a customer loyalty platform, which he simply called SaaSquatch. And since low-to-mid-tier pricing had worked with Referral SaaSquatch, he copied this earlier approach, positioning his new product significantly below his biggest competitor.

By early-2018, SaaSquatch was driving massive commercial gains for its clients.

Fraser told the Predictable Revenue podcast that, with its new functionality, SaaSquatch customers usually enjoyed returns of five- to ten-times their initial investment. When word spread about SaaSquatch, leads started pouring in. And, according to Fraser, they were gliding through the sales funnel with very little help from his sales reps.

At first, it felt great to see SaaSquatch’s customer numbers rising and its revenue growing, but the thrill quickly wore off. And when Fraser saw customers paying tens of thousands of dollars upfront without a single comment on the price tag, he knew his pricing had to change—but how?

An engineer by trade, Fraser says his first thought was to run the numbers. He started by exporting the previous quarter’s sales numbers from his CRM and dumped them into Excel. Then he went through the data, sale by sale, checking how many deals his sales reps had discounted.

Next, he analyzed the discounts by service tier. SaaSquatch offers three tiers—Pro, Enterprise, and Managed—each one a little more advanced than the last. After segmenting his sales data by tier, Fraser discovered his reps weren’t discounting all tiers equally.

“What was interesting is that we were selling the majority of our most popular plan at full price and our discounts were actually being offered in our lowest plan,” said Fraser. And when he cross-referenced his sales data with his support metrics, he discovered something even more surprising: the customers pushing for discounts also had the highest support costs.

In other words, they were paying the least and costing his business most.

Fraser knew something interesting going on but he wasn’t sure how to translate it into optimal pricing. So he built a pricing model in Excel that allowed him to tweak product pricing and conversion rates to investigate the change on his bottom line.

“Let's take the worst-case scenario: we'll sell none of [the Pro tier],” said Fraser. “Okay, well what does that look like?” Even in the worst-case scenario, he figured out he was still making more money. At their new higher price points, SaaSquatch’s Enterprise and Managed customers more than made up for the projected loss in Pro customers.

Even if Fraser lost all of his Pro customers, he estimated a four- to five-percent uptick in revenue.

Fraser’s analysis convinced him the pricing experiment was worth trialing. And after much testing, he landed on some pretty ambitious increases: a 30 percent increase on the Pro tier, a 25 percent increase on the Enterprise tier, and a huge 80 percent on the Managed tier.

And to hammer home how serious he was, Fraser set two more rules for his sales reps. One: No discounts. Two: All customers had to pay for 12 months upfront. “I put myself in a boogeyman role,” Fraser said. “I told my reps that they might think this is impossible but they’re going to do it.”

The day came when Fraser flicked the switch and sat back to watch the results. And then, nothing happened. The phones went dead, SaaSquatch’s inbox dried up, and Fraser and his sales reps started shifting nervously in their chairs.

For the first few weeks, SaaSquatch’s sales reps just couldn’t land a sale. Their leads hemmed and hawed and said they’d have to think about the new pricing. As the first month of the pricing trial came to a close, SaaSquatch’s sales team had no new customers in the bag.

“Me and the sales reps are looking at each other saying, ‘Well, that was a really bad experience. It did not work. We've got no deals closed. We've clearly pooched the entire thing,’” Fraser said.

He was facing down disaster and he knew it was his reputation on the line. “If it failed, it was on me,” says Fraser. “It was clearly a disaster but we had to hold the line, we had to ride it out.” So he waited and watched as the days ticked away, bringing him and his team ever closer to an embarrassing defeat.

“The sales team suddenly realized that they could do this,” says Fraser. The floodgates opened and Fraser’s team was suddenly awash with new business.

Reflecting on the pricing change, Fraser says that the new, higher price probably scared off a lot of his smaller prospects, which caused the initial drop in sales. But that wasn’t necessarily a bad thing as it freed up his sales reps’ time to focus on Enterprise and Managed tier prospects. And while bigger leads took longer to close, they were worth far more to the business.

In fact, Fraser has doubled down on that approach, telling his reps that they’re allowed to ignore Pro deals if they focus on bigger prospects.

The pricing switch also had a huge impact on the type of lead coming in. “We've always had customers in the Fortune 500, but we're seeing an increasing number of large companies coming in because of the pricing increase,” said Fraser in 2019.

And those customers are more than making up for SaaSquatch’s smaller losses. “We've seen a pretty strong increase in pipeline and not just in dollars, but the actual number of accounts,” Fraser said. “We've seen about a 34 percent increase in new opportunities and new leads.”

Fraser’s pricing gamble has resulted in a significant increase in revenue for the company. But he’s also decreased SaaSquatch’s operational costs by scaring away the small but demanding clients on the Pro tier. And that’s put SaaSquatch in an excellent place for the future.

Fraser says SaaSquatch’s pricing is far more than a way to make profit. It’s also a means to position the product in the market. Two years ago, Fraser recalls pitching to large 500- to 3,000-person organizations. Time after time, prospects seemed interested but were put off by the price. SaaSquatch wasn’t charging an enterprise price, so it couldn’t possibly be offering an enterprise service—or so the buyers thought.

But after increasing his pricing, Fraser sees a difference in perception.

SaaSquatch is no longer the cheaper alternative or passable backup. It’s a viable customer loyalty product for organizations of all sizes—and it has the price tag to prove it.

And with sales continuing to rise, Fraser is determined to keep pushing. “When we started, we charged $25 per month for our bottom plan,” he says. “Now, our bottom plan is $1,250 a month. Realistically, we want to keep pushing until our bottom plan is more than $5,000 per month.”

By taking risks with his product’s pricing, Fraser is moving closer to his optimal pricing structures all while cutting support costs, boosting revenues, and positioning SaaSquatch for a new era of success.

“We were terrified during our first pricing experiment,” says Fraser. “We had no idea what was going to happen—but we stuck with it and held the line and it worked. I don’t think we’ll have that level of fear when it comes time to do it again. It was honestly the best business decision we could have made.”

But most of those users were microbusinesses and freelancers on Hippo Video’s free tier. If Mariappan wanted to turn Hippo Video into a long-term success, he knew he had to close bigger clients.

At an all-hands meeting, Mariappan challenged his team to come up with a way to reach support, sales, and marketing leaders at larger organizations. Someone suggested doubling down on their content marketing. Someone else suggested they tried display ads. Mariappan shook his head. The ideas were good—but he wanted great.

And then it hit him: what about jumping straight to a face-to-face conversation with a personalized video in the outreach email?

Within one year, Mariappan’s personalized videos had increased his sales reps’ email response rate by 300 percent and increased Hippo Video’s average deal size from $150 per month to more than $2,000 per month.

Mariappan knew personalized videos would work—he had watched his customers successfully implement video content for years—but he didn’t know how they would slot into Hippo Video’s sales strategy. So he sat down with his sales development reps and asked where they thought a video message could be useful.

Their response was unanimous: they needed it early.

Most of their leads were still coming through Hippo Video’s inbound marketing campaign, so their prospects already knew about the company and its products. Because of this, Hippo Video’s initial sales outreach wasn’t so much about selling the product as it was about selling themselves.

And that was proving tricky now that they were targeting larger organizations. Busy support, sales, and marketing leaders reviewed their options with ruthless efficiency, making decisions long before Hippo Video’s sales reps had struck up a rapport.

Once Mariappan knew where the video content would go, he had to work out what to include. For that, he turned to Nikhil Premanandan, Hippo Video’s Head of Marketing.

Premanandan was running Hippo Video’s inbound marketing campaign, attracting a healthy stream of leads through content marketing and paid search. Because leads were inbound, Premanandan says they already knew a fair amount about the product.

“These leads had searched for Hippo Video and knew about our product,” says Mariappan. He suggested they double down on the sales reps’ suggestion and focus on presenting the sales rep as a person.

After confirming the location and content of the video, Mariappan had to distill everything down to a practical script for his reps and asked Premanandan to help. “We iterated a few times, trying to create the best script,” says Premanandan. And that was a tough job. Mariappan says they limited the videos to just 60 seconds and insisted that the sales reps record and edit everything themselves. After several weeks of revisions, Mariappan presented the final script to the sales team: a brief personal introduction to the sales rep and an invitation to book a call.

Hi <First Name>,

This is <SDR Name> from Hippo Video. I just wanted to quickly introduce myself to you and thank you for signing up with us.

I will be your account executive going forward. If you have any questions about Hippo Video just reply to this email and I'll help you out.

I’d like to get on a call to understand <Company Name>'s goals using videos and how Hippo Video can help you. Just click the 'schedule meeting' button at the end of this video to schedule a demo with me.

I look forward to meeting you.

Have a great day!

Premanandan says the script isn’t complicated—and that’s kind of the point. Hippo Video’s sales reps don’t demo the product or go for the hard sell. Their videos are designed to feel like an ongoing conversation between two people who already know each other.

The personalization in the script is fairly lightweight, too. In the standard script, only the sales rep’s name, the prospect’s name, and the company name change. And Premanandan says his sales reps already have all the information they need when the lead is inbound. For outbound work, he says you can find this information on the company’s LinkedIn page.

Premanandan shared an example of a personalized sales video with Copper.

On the video thumbnail, you can see one of Hippo Video’s sales reps, Corrado. He’s holding a whiteboard, which says, “Hi Austin! Welcome to Hippo Video.”

When you click play, Corrado launches into the script with a friendly exuberance. It doesn’t feel like a sales call. It feels like a personal connection asking you to an informal coffee.

The one script variation kicks in when a prospect asks about upgrading from the free package to a paid package. In these cases, Hippo Video’s sales reps make personalized recommendations on how they could use it better.

“We look at how a prospect is using Hippo Video and make personalized recommendations to them,” says Premanandan. “For example, if they’re not using a particular feature that might be useful to their business, we’ll point it out and offer some best practice advice.”

In August, 2018, Mariappan rolled out his personalized video strategy to Hippo Video’s entire sales team—and the result was phenomenal.

And it wasn’t just a quantitative improvement. According to Premanandan, prospects responded exceptionally well to the personalized videos. “There were a lot of people who actually said, ‘Hey, I saw your recent video. Thanks a lot, it was really good.’”

But behind all the success, Mariappan saw a subtle flaw in their sales strategy—his new personalized videos were great for interesting hot prospects, but they didn’t effectively engage cooler leads.

Mariappan realized one of three things happened when a prospect reached the end of personalized sales email.

1. They were interested and emailed right back.
2. They weren’t interested and deleted the message
3. They wanted to know more, so they clicked through to Hippo Video’s website.

The first outcome was the ideal scenario. When Mariappan’s sales reps got a positive response, they spun into action, guiding the interested prospect through the sales funnel. The second was problematic but Mariappan fixed it with a drip campaign—the sales rep’s CRM sent a sequence of emails to coax them back to the conversation. But the third outcome proved a more difficult problem and Mariappan was determined to fix it.

When a prospect reached the end of a personalized sales email and wanted to learn more, they sometimes clicked through to Hippo Video’s website. But the link went straight to the standard homepage, which displayed the same messaging for every single visitor.

After a highly personalized first touch, an unpersonalized website was disappointing. Mariappan says he spoke to several prospects who felt let down when they clicked through only to find that Hippo Video’s personalized messaging had given way to a decidedly generic homepage.

Mariappan knew they needed to deepen the personalization experience to engage this segment of users. So his engineers quickly built a landing page editor for his sales reps. Using the editor, they could quickly create an additional personalized landing page on a subdomain of Hippo Video’s website and link to that page in their emails.

Now, if a prospect wanted to learn more, they were sent to a landing page specifically tailored to them rather than a website homepage designed for everyone:

Like with their videos, Mariappan insisted his sales reps kept the landing page simple. The header features Hippo Video’s logo and some personal details about the sales rep. Below it is a customized headline tailored to the prospect.

One landing page Premanandan shared with Copper read: “Alex, are you ready to generate more leads with video?” Alongside the headline is another personalized video, which again introduces the sales rep and prompts the prospect to book a call. At the bottom of the landing page, there’s a button linked to the sales rep’s calendar. It’s a simple design and, like the personalized videos, can be developed and deployed in a few minutes.

And it works, too.

Premanandan says each landing page actively engages the prospect in the conversation and prompts them to take the next step. The landing page feels more like a personal invitation to a meeting rather than an anonymous sales email. “The response has been tremendous,” says Premanandan. “We are getting about 80 to 90 percent in open rates and up to 80 percent in response rates.”

Mariappan compares Hippo Video’s service to a personalized shopper in a high-end retail store. When you walk into Barneys, Saks Fifth Avenue, or Macy’s, everything is about you. Your personal shopper greets you by name, makes style recommendations, and is there whenever you need something. From the moment you walk in to the second you leave, everything is about you and your needs.

Mariappan wants the same for his customers. His goal is for them to see Hippo’s reps as personal consultants, not faceless drones. By personalizing Hippo Video’s sales strategy, Mariappan does just that. From the moment a prospect receives an initial outreach email, everything is tailored to them.

By personalizing their sales strategy, Mariappan’s sales team has driven enormous growth for Hippo Video. In just one year with their new strategy, Mariappan has increased his company’s average deal size from $150 per month to more than $2,000 per month.

But Mariappan says he’s still not satisfied. He wants to push personalization deeper into the company’s workflows. Adding personalized videos and landing pages into Hippo Video's sales process, he says, is just the tip of the iceberg. In the future, Mariappan plans to roll out personalized elements to marketing, sales process, product, and customer service.

“Eventually,” he says, “we want people to say that Macy’s customer experience feels just like ours.”

Just two years earlier, he had joined SnackNation, a healthy-snack delivery startup as its third sales hire. Starting with a blank slate, Dorsey designed an industry-leading playbook, recruited dozens of new sales reps, and drove relentless revenue growth. When he left the startup in 2017, he had grown the sales team from three to 55 reps and had increased the startup’s earnings by 11X.

But PatientPop was a new kind of challenge.

At SnackNation, Dorsey had engineered everything, himself. He could design his sales playbooks with complete autonomy, pick and choose who he hired, and manage every last second of the onboarding process. At SnackNation, it was his sales organization from top to bottom.

But PatientPop already had a large sales team with deeply embedded sales strategies. And to make matters worse, they were underperforming.

Dorsey knew that fixing a large sales team was a tough ask. It’s like steering an oil tanker: you turn the wheel—and have to wait 30 minutes for the bow to move. But he was confident in his abilities and accepted the offer. And just eight months into the job, Dorsey has driven amazing change at PatientPop, growing his team from 40 to 80 sales professionals and doubling revenue from inside sales. But it didn’t start with wholesale strategic change. Instead, Dorsey focused on fixing the sales organization’s culture.

In the summer of 2013, PatientPop’s founder Luke Kervin and his wife were expecting their first child. And like most soon-to-be parents, they expected the healthcare system to run like a smoothly oiled machine. But their experience as the opposite; there were long waits, scheduling appointments was a nightmare, visits were rushed, and the doctor overlooked a test result that could have been disastrous. But when Kervin's frustration died down, he saw an opportunity.

Every single medical professional Kervin spoke to complained about the lack of innovative technology in healthcare, specifically in the practice management space. So Kervin gathered a small team, built a new streamlined practice management and marketing platform, and released it to the public in 2014. The product, which Kervin named PatientPop, took off like a rocket.

Kervin started with just three employees and a handful of clients. Now, he employs over 400 staff and supports 5,000 customers. When Dorsey joined PatientPop in 2018, he realized much of the company’s success was thanks to circumstance—not strategy.

But Dorsey saw potential in the growing startup. It was a great product with a huge market—all it needed was someone to whip the sales team into shape and turn PatientPop into a billion dollar medical unicorn. To get there, Dorsey knew he would have to rebuild the entire sales organization. But his first job wasn’t overhauling the corporate sales strategy or writing a new playbook.

It was getting to know his staff.

Dorsey is a big believer in culture. The phrase culture trumps strategy is something of a personal motto. And it’s not just an empty phrase, the science backs it up. A study from Harvard Business Review showed that an optimistic and happy salesperson typically outsells an unhappy salesperson by 37 percent. But when Dorsey joined PatientPop, the sales organization’s culture didn’t fill him with confidence.

There was no buzz on the sales floor and sales reps didn’t take ownership of their performance. And that’s a problem because installing a culture is hard when you’re a new face in a team. “From a culture perspective, I'm outnumbered,” Dorsey says. “The culture can't come from me. I can give the vision of what I’m trying to do, but I can't drive the culture.” Dorsey knew that culture had to grow from the bottom up, so he spent his first few weeks just talking to his team members.

As a new boss, Dorsey knew he couldn’t expect his reps to instantly open up about their goals, ambitions, or performance.

So Dorsey ran regular one-on-one interviews with his sales reps and started asking what was wrong with the organization and what they could do better. He asked about roadblocks and wishlists and frustrations. And when he got them talking, he moved onto culture. “What type of culture would you like to be a part of?” Dorsey asked. “If you could describe the perfect organization, what would that look like to you?”

After interviewing 50 people, Dorsey had a good idea of the type of culture his reps wanted to build. “They want to win, they want to get better, and they want to have fun,” he says. And because the culture came from the reps, it didn’t feel imposed.

Dorsey says this strategy quickly secured buy-in from his sales reps. Now, he could start implementing small, low-level changes to make that culture a reality.

During his initial one-on-ones, Dorsey heard a couple of topics popping up again and again. One of them was training. Specifically the lack of it. “Training was a big one,” Dorsey says. “There was no ongoing training. A lot of new reps hadn’t been trained at all.”

Training is one of Dorsey’s pet peeves. He wrote an influential LinkedIn article back in 2016 titled The Sales Industry Is Backwards. “We as an industry are the only high-paying professional industry that is responsible for teaching and training its own people from the very beginning,” wrote Dorsey. And his experience at PatientPop vindicated his complaint.

Brand new sales reps were being thrust into frontline sales positions and expected to hit the same quotas as seasoned pros. They felt lost and confused and fumbled their way through the job. It took these reps four months to hit their quotas.

Dorsey immediately implemented a strict onboarding regime. “I have a four-to-six-week onboarding program where nobody hits the phones in that time,” said Dorsey in a January 2019 interview with Costello.

The onboarding process put a lag on hiring. A sales rep would join but only start generating revenue after six weeks. But Dorsey is happy to take that initial hit. With his new training method, new reps started hitting their quotas in two months instead of four. “I think what gets us here is that reps can have the practice and can go through the demo situation without any fear of failing,” said Dorsey. “The practice and repetition are so helpful as new reps learn how to be creative and think on their feet.”

Another common thread in Dorsey’s one-on-ones with his reps was communication. HIs sales reps told him that they were generally left to get on with their job on their own. Communication was minimal and inconsistent.

From his first day, Dorsey made sure he was an approachable presence on the sales floor. “I walk through the office every day, giving people advice, asking where we’re at right now,” Dorsey says. And even after eight months in the job, he’s careful not to ask about performance. After all, he doesn’t really have to ask, he’s got all the performance data he needs in a sales dashboard.

Instead, when Dorsey is talking to his reps, he’s asking how they’re doing or how they’re feeling. He uses his informal chats as an opportunity to generate qualitative information about his team. If there’s a big deal coming up or a logjam on the horizon, Dorsey wants to know so he can help out where he’s most needed.

Beyond simply being present, he has also rolled out regular sales department meetings, something he says simply did not happen before he arrived.

By discussing how everyone is doing as a group, there’s nowhere to hide. It encourages people to take ownership of their performance, something Dorsey says is a core part of the culture he’s building.

Finally, Dorsey introduced Ambition, a goal management platform. “PatientPop always had a great recognition culture but the recognition was always hidden in Slack,” Dorsey said in video for Ambition. But now, he’s got PatientPop’s sales data up on big screens. Everyone’s sales performance is completely transparent. Again, it’s about creating accountability and keeping people committed to their goals.

Many people associate corporate culture with extravagant office parties and away days. But Dorsey says this is totally wrong. Fun is the very last piece of the culture jigsaw. “Culture is all the other things,” says Dorsey. “And because you do the other things, you can have fun.” So when Dorsey had established PatientPop’s new culture, he turned his attention to fun.

PatientPop’s sales team hadn’t been out together in years. Sales reps who worked a few feet away from each other still didn’t really know each other. That hurt the team’s culture as colleagues who don’t know each other won’t ask for help or celebrate wins or call people out when their standards slip.

In his first few months, Dorsey arranged a couple of happy hours and he’s got a couple of bigger events lined up. “We're doing a beach day next Thursday,” says Dorsey. “We come in, crank for a half day, and then go down to the Santa Monica pier. We’ll go to the arcade for a few hours, go to the beach, play volleyball, and go do a happy hour.”

All in, it’ll cost a couple thousand dollars. But to Dorsey it’s not an expense, it’s an investment. If the trip makes Dorsey’s sales reps a fraction happier and causes a one percent uptick in their close rate, he’ll make his investment back in a couple of hours.

Dorsey knew focusing on culture first would pay off. He’d read the science and knew that a happy team would consistently outperform an unhappy team—but he still felt apprehensive during his first few months.

He’d come in as the Vice President of Sales. He was responsible for all the revenue coming into the company and reported directly to the CEO, Luke Kervin. Yet despite this senior leadership position, he’d spent his first two months just talking to his sales reps, solving minor problems, and formalizing the team’s culture. If you didn’t know how important culture is, it might have felt like Dorsey was wasting his time.

As his first quarter at PatientPop rolled to a close, Dorsey pored over his sales performance data, searching for proof that his approach was working. And he found that proof in spades.

He’d tripled PatientPop’s lead conversion, doubled revenue from its inside sales team, increased field sales revenue by 1.5X, and improved conversion rates from 15% to 26%.

Dorsey laughs at his detractors who describe his work on culture as a waste of time and money.

“Go ahead and treat your team like crap,” Dorsey says. “I won’t and I’ll beat you in the long run.”

The message piqued Hurst’s interest, so she clicked into the target company on LinkedIn’s Sales Navigator and began investigating. It was an international baby food manufacturer with offices all across Europe.

After a quick search, she found the company’s managing director, Rachel, on LinkedIn and sent her a connection request. A couple of days later, Hurst’s phone dinged with a notification. Rachel had accepted her invite. Immediately, Hurst hopped on LinkedIn and bashed out a message. “Hi Rachel,” Hurst wrote. “It’s great to meet you. Do you have time for a quick chat about your business travel needs?”

And then… nothing.

Hurst could see that Rachel had read the messages but she never replied. Hurst tried sending a handful of follow-ups but nothing elicited a response.

After several weeks of complete silence, Hurst was ready to mark the lead as lost—but then she remembered an idea from a recent sales training workshop. Using something called a trigger event, Hurst would tempt Rachel into a conversation, engage her in the sales process, and eventually close her as a customer.

In fact, Hurst would go on to use trigger events to kickstart dozens more conversations over the next 18 month, improving her overall close rate from 26 to 63%.

When Hurst joined Corporate Traveller UK in 2017, it was already an established company with a mature sales team. Everything seemed to run like a well-oiled machine. All of Hurst’s prospecting was done externally and leads were fed into a central CRM. Each month, a sales manager assigned Hurst and her colleagues a handful of new leads. After that, it was left to Hurst to employ whatever sales strategies she deemed fit.

And while Hurst was very successful—she was selected as a top-performing employee across the whole of Corporate Traveller UK—she occasionally hit dead ends like with Rachel.

Hurst’s colleagues hit similar problems. They’d find a lead, make the connection, and then everything would shut down. It was frustrating as they knew they could help out the prospect, but only if the prospect were willing to speak to them. Short of turning up at their prospect’s offices unannounced, they couldn’t see a solution.

Precisely what counts as a trigger event depends on what you’re actually selling: A recruitment consultant will look for companies posting job ads, a human resources company will look for organizations with a rapidly growing headcount, and a public relations firm will keep an eye out for anyone winning awards.

For Hurst, who was selling a business travel management platform, a trigger event was anything that suggested a company was expanding into new territories or opening new offices.“Some example triggers include seeing that a lead has just opened a new office in America or noticing that they have just raised more investment,” says Hurst.

But identifying good trigger events for her business was just the start. Hurst still had to work out how to monitor her target companies and pick out possible trigger events as soon as they popped up.

Tracking just one company is difficult, especially when its activity is scattered across half a dozen social media platforms, its own website, guest content on other sites, press releases, interviews, and so on. Manually tracking multiple businesses simply isn’t practical. Faced with this problem, Hurst and her colleagues designed a lightweight monitoring system that could be set up in half an hour and reviewed in a couple of minutes.

For example, if a company has recently raised a new round of funding or recruited a senior member of staff, Sales Navigator will flag it immediately and add a note to the company account. For larger deals, Hurst says she also adds senior individuals like CFOs, CEOs, and managing directors. Adding individuals gives her a more granular look into the business and helps identify smaller trigger events that she might otherwise miss.

Next, Hurst sets up a custom Google Alert for each company with a weekly update schedule. “On Fridays, I get a list of any Google alerts that relate to my target companies,” Hurst says. “Then I work through the list picking out any positives.” The Google alerts typically flag any news to do with the company so there’s a lot of irrelevant updates to comb through. But after a couple of months reviewing the alerts, Hurst says can now scan through each update in a couple of minutes. At that point, with everything set up, the waiting game begins.

Back in early-2018, Hurst was ready to consign her baby food lead to the bin. It was a relatively poor lead to begin with. The company’s address was a PO box, there was no phone number on the website, and no one had a personal connection to anyone who worked there. The managing director was Hurst’s only route into the company—and she was ignoring all of Hurst’s messages.

After a couple weeks of silence, Hurst decided to give the trigger event strategy a shot. The sales trainer had only recently delivered his presentation and Hurst and her colleagues were still a little reluctant to invest time into the new tactic without any proof that it worked. But with the lead going nowhere, Hurst was willing to try anything. She added the company to Sales Navigator and set up a Google alert for the company’s name. Neither returned any useful information so Hurst pushed the lead to one side and turned her attention to other leads.

But a couple of days later, her new strategy threw her a lifeline.

One Friday, a Google alert dropped into Hurst’s inbox. It contained a news story saying her target company had just been included in The Sunday Times Fast Track 100, an annual list ranking the UK’s fastest-growing companies. It was the perfect trigger event: a feel-good award and a sign that the company was gearing up for expansion.

“I went back to the managing director and put a message together saying, ‘Hi Rachel, congratulations on your Fast Track 100 inclusion. It's great to see a company preparing for great global expansion!’” Then she clicked send and sat back to wait.

Rachel responded almost immediately, thanking Hurst for the compliment. And that small interaction was the in Hurst needed. “It was now a warm introduction and I was likely to get further in the sales process,” Hurst explains. Over the next few weeks, Hurst talked Rachel towards a meeting. And after that, towards a proposal and a sale.

In late 2018, Rachel signed on the dotted line and Hurst celebrated another closed deal. “They've been with us for a few months now,” says Hurst, smiling. “ It's been a very successful relationship.”

That success solidified the success of the sales strategy in Hurst’s mind. Over the next year-and-a-half, she set up trigger event monitoring for all new leads—and the results were phenomenal. In just 18 months, Hurst has improved her close rate from 26 to 63%.

Hurst says she knows that event triggers alone can’t produce an effective sales strategy. “Trigger events are a perfect scenario, but the reality is that they don't happen all the time,” Hurst says.

But she’s always on the lookout for a trigger event to provide a way in. And when one pops up, she’s ready to pounce.

After she introduced her trigger event strategy, Hurst noticed a clear improvement in her sales performance. In the past six months, she can point to 20% of her clients that she wouldn’t have closed without trigger events. But the improvements didn’t stop there.

After seeing Hurst’s success, Corporate Traveller UK rolled out the strategy across the entire sales team. “Trigger events give you a personalized icebreaker with a prospect,” says Hurst.

“You might have to be patient, and you definitely have to do your due diligence, but it’s worth the effort. They turn cold emails into warm introductions—and that’s always going to result in more sales.”

She built a list of her ideal clients, researched their businesses, planned how she could help them and personally reached out to the key decision-makers.

And then… nothing.

After several months, Meyer realized her direct sales approach wasn’t working. “When we approached these brands, they probably weren’t considering expanding into Japan,” explains Laurène Oudart, Tokyoesque’s research project manager, in an interview with Copper. “Also, in Japan, personal introductions are really important. It’s difficult to get access to the right person without one.”

After several quiet months, Meyer eventually landed a high-profile job with Twitter after being contracted by an established marketing agency. And that gave her an idea. Instead of selling directly to customers, Meyer could build a robust referral network and have her partners find work for her. In just five years, Meyer has built a far-reaching referral network that established a consistent initial pipeline, allowing her company to grow from two clients to more than 40.

When Meyer founded Tokyoesqe, she had plenty of experience in the industry. She had worked for several leading Japanese marketing companies and spent three years at Nielsen as an analyst. But personal experience only got her so far. Few people outside of Meyer’s immediate network had heard of Tokyoesque and no one was willing to take a shot on the fledgling company.

But in the winter of 2014, the company caught its first break. Meyer was scouring the British market looking for opportunities when she saw a large digital agency had won a contract to help Twitter run a new global marketing campaign.

“Twitter wanted to have pictures of their users in three different countries, including Japan,” Oudart says. Meyer immediately fired off an email, explaining that she owned a company with employees already in Japan. If the agency needed help, Tokyoesque was the perfect partner. Twitter agreed and suddenly Tokyoesque was working with a social media giant worth $30 billion.

That instant success provided a blueprint for Tokyoesque’s future referral network. All Meyer needed was a dozen more agencies referring a dozen more projects.

She knew that organizations entering the Japanese market would look for local professional services like accountancy firms and law firms. So she started by building a list of all the professional services companies in Tokyo.

Next, Meyer whittled that list down using a rigorous screening process. Since she needed partners of a similar or larger size, she discarded companies she deemed too small, as their referred projects meant little in terms of profit. She likewise avoided companies that were too large, since they’d probably want a big-name partner.

Meyer then evaluated how established each potential partner was in the Japanese market.

When she had whittled the list down, she pitched her deal to the remaining firms. According to Meyer, this was a mutual referral arrangement with a monthly, quarterly, or yearly quota, which usually sat around 5 to 15 percent of revenue.

The response from her initial outreach was incredibly positive. Potential partners saw the value in what they were offering and a handful signed up immediately. The small referral network was a proof of concept and provided a steady flow of leads into Tokyoesque’s sales pipeline. It wasn't enough to drive rapid growth, but it was enough for Meyer to bring on her first new hires—mostly translators, project managers, and operations specialists— to handle the new workload.

With her referral system in place, Meyer could begin to expand her network with the best-performing referral partners. She recruited a wide range of partners, tracking exactly how much work they referred to her. And after a few more months, she identified the best-performing category: design, marketing, and insights agencies. All she needed to do was find and recruit them.

Meyer set up online alerts on LinkedIn, Twitter and Google, monitoring the industry for the telltale signs that an agency had won a contract related to Japan. And whenever an alert popped up, one of the Tokyoesque team would reach out, offer to help out, and pitch them on the referral agreement.

After a couple of years, Tokyoesque had significantly grown its referral network and it was generating dozens of leads into their sales pipeline every week.

But as the network grew, Meyer noticed a problem: how do you keep every partner happy?

By 2017, Tokyoesque had developed a large network of partners—and it was proving difficult to manage. “The hard part is to ensure we keep those relationships hot and that both of us don’t forget the other,” Meyer says.

Instead of just trying harder and hoping for the best, Meyer decided to formalize her referral system. There were two parts to her new structure: account managers and quotas.

First, she divided up Tokyoesque’s referral partners and assigned them to different staff members. Each was responsible for maintaining and strengthening the relationship at each referral partner. Often, this took the form of a simple email, checking in and asking how the organization was performing. Other times, it was a more in-depth meeting to discuss where Tokyoesque could support their work. Occasionally, it was just a friendly call to chat through weekend plans.

Tokyoesque’s personalized account management also helped Meyer identify potential outbound sales opportunities. Often, partners didn’t realize what the company could actually help with. But now that Meyer’s colleagues were proactively asking about their workload, Meyer had an up-to-date list of potential pitch opportunities.

“If we don't keep in touch, we don't know what they’ve been working on and we might miss something,” explains Oudart.

The second part of Meyer’s new structure was a quota system. During her negotiations with each referral partner, Meyer tried to estimate how much work each they should pass to each other. But what she’d found is that it was difficult to remember where leads came from, especially if they had long sales cycles. That left both parties wondering if the referral agreement was actually working for them.

But with her new system, each person had to log leads in a CRM whenever they were sent or received. With tracked leads and a quota system in place, Meyer now knew exactly how much work Tokyoesque had sent to a partner and how much work they had received in return. And that allowed Meyer’s employees to follow up on old leads, asking whether their referral partner had closed the deal. That followup helped remind the partners about all the work they had recently referred, which kept the relationship hot.

Meyers didn’t expect sales to be a challenge for Tokyoesque. She was confident in her skill set and she knew she could offer real value to her customers—all she needed was an opportunity to pitch. But she quickly found that just couldn’t get those opportunities via a direct approach—and neither could professional sales reps.

Since founding Tokyoesque in 2014, Meyer has tried to build out an outbound sales team on three different occasions—and each time, she found herself unsatisfied with the results.

It may have been a blessing in disguise.

Because her outbound sales efforts didn’t work, she was forced to try alternative strategies and discovered how effective a referral network could be. And with her burgeoning referral network continuing to generate leads, Meyer says she isn’t even thinking about trialling outbound sales again—she plans to double down on what’s working.

“My next goal,” says Meyer, “is to build out a partnerships department rather than a sales department and focus on growing the network.”

So, on the long drive back home, she resolved to create a better, more accessible networking group.

The next morning, Barlow started a LinkedIn group called Like Minded Females. Then she invited her LinkedIn connections to join. The group filled up and quickly became a hotbed for discussion, debate, and news. The next week, Barlow created her first event: a networking brunch—and opened up ticket sales to her community members.

By the date of the brunch, Barlow had received dozens of responses and was preparing for a sizeable turnout. But when she turned up at the venue, all she found was an empty table. “No one showed up,” says Barlow in an interview for Copper. “That was our first failure.”

But Barlow didn’t let her initial failure derail her plans. Instead, she drew upon her analytical background, iterating and experimenting with her approach to improve her community sales strategy.

Over the next 18 months, Barlow turned her vacant brunch into a thriving event, attracting over 100 attendees each month. And Barlow is funneling her rapidly growing profits back into her business. Next year, she plans to turn her venture into an online learning platform.

Barlow knew that building a community was going to be key to the success of her networking events. “There's a study out there that says 83 percent of your customers come from word of mouth,” Barlow says. “Having a community is the same idea but you are proactively creating those interactions.”

All she had to do was work out how to nurture her community so that it fostered those interactions.

For her next event, Barlow planned to seed her brunch with handpicked attendees. She combed through her personal network, looking for people who matched her ideal customer profile—young women who were new to London and wanted to grow their personal network. She found three and personally invited them to her next event.

“The great thing was that they hadn't met each other so it felt like a real networking event,” Barlow says. “It was about meeting new connections, learning, and sharing.” The brunch proved to Barlow that her product was worthwhile and, perhaps more importantly, it validated her networking event to her potential customers.

With her community’s initial hesitation out of the way, Barlow began thinking about how to drive more ticket sales. Her solution was simple: grow the community.

Initially, Barlow’s Like Minded Females community had grown slowly by word of mouth. She needed a way to promote what they were doing and drive more traffic back to her LinkedIn group. For that, she turned to Instagram.

At every event, Barlow made sure she collected photos, videos, and quotes, later sharing them on social media. “It was all about creating empowering content so people could discover what we are doing visually,” she says. Her plan worked. New members began flocking to Like Minded Females, growing her community and boosting event attendances.

Barlow says her business was built on failures or, more precisely, on the lessons she learned from them. And as Like Minded Females has continued to grow, Barlow has doubled down on this idea, adopting a ‘failing forward’ mentality. “Every time we fail, we fail better,” she says.

One of these failures occurred when she tried to expand her community to new platforms.

In June, 2019, Barlow decided to experiment with new platforms beyond LinkedIn. Her LinkedIn group was good, but it didn’t facilitate the informal conversation that communities thrive on. After comparing a few different options, Barlow selected WhatsApp as her next platform. But after a few weeks, it was clear something was wrong. Users were posting their own sales and marketing messages into the WhatsApp group, turning the feed into a maelstrom of competing messages. After several attempts to implement a moderation system, Barlow admitted defeat and ditched the WhatsApp group.

But she learned from her failure and tried again. Barlow was sure that her community still needed a place for informal conversation, so she launched a Slack workspace. Since the workspace was split into channels—events, general, promotion, and so on--it was easier to keep conversations on track. And it also gave Barlow better access to her community members.

Barlow says she had to learn from another mistake when she realized she had misjudged the make-up of Like Minded Females. “I thought our community was young professionals, who were working in a very masculine environment and who needed help,” Barlow explains. But that narrow definition alienated huge swathes of Barlow’s potential market.

As Like Minded Females grew, she began receiving messages from people outside their target demographic asking if they could join. And while Barlow assured them that they were welcome, the fact that they had to ask proved that something was wrong.

Barlow says she now runs 12-week sprints, during which she analyzes and optimizes different parts of her community and business. For example, she recently reassessed her brand messaging, removing all language related to younger women and refocusing her strapline on more general female empowerment. She now calls her community a “diversity and inclusion network,” which ensures everyone is a potential customer.

In August, 2019, Barlow passed a major milestone. Like Minded Female’s monthly events, which were attracting a handful of personal connections just last year, were now pulling in attendances in excess of 100 people.

Barlow attributes her success to the community that she built from scratch. And it’s a sales resource that will continue paying dividends. In 2020, Barlow plans to take her events back online, creating a range of e-learning resources. With her community already in place, she has a pre-made customer base for her new products, which she is confident will kickstart sales.

She thinks other businesses could learn from her approach.

“People sell to people,” says Barlow. “And the best way to support that is with a community. You are creating spaces and opportunities for people to come together and turn a personal interaction into a sales opportunity.”

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