Account Executives in SaaS: What It's Really Like

Surprisingly, I’ve noticed that even those who work in other departments in tech are completely mystified about what actually goes on in the hyperactive, bustling and loud sales pods.

Sales, in general, is typically portrayed in pop culture (before the millennial era anyway), through films highlighting a male-dominated and often corrupt line of work (Think: Wolf of Wall Street, Glengarry Glen Ross, Mad Men). Smoky billows of cigarettes fill the space between suited men and eager clients with pens in hand, ready to sign away thousands on grandiose promises. A smartly dressed, well-coiffed boss bellows “coffee is for closers!” intimidatingly across a room of young, gawky salesmen itching for their shot at a million dollar deal.

Pop culture did get one thing right: coffee—and lots of it!

Sales is a highly strategic art that begins before any actual contact with a buyer and ends long after the deal is signed.

Today, most of us understand the general concept of sales as selling a product or service to a prospective customer, but there’s so much more to it than that. I’ve outlined six surprising truths gathered from my years of experience on the front lines of client-facing sales roles in the hopes of revealing an experience that’s less Hollywood and closer to the truth about the SaaS (Software as a Service) sales world.

Strategic sales is consultative, which means that the customer’s business needs are crucial when deciding whether or not they need certain types of software.

I’ve talked to countless individuals who stumble upon the software I sell, Copper, which is recommended by Google and borrows from Google’s intuitive UI (user interface, for the non-techies reading this). But sometimes they lose sight of the fact that they’re looking for a wholly different sort of tool and their needs are clearly different from what I can promise them.

It is in both my best interest and the prospect’s best interest to be completely honest in order to avoid turning them into a customer who realizes down the line that they actually need an entirely different product for a completely different business problem than our tool can solve. Sales is about creating mutually beneficial business relationships—not just at the time of the sale, but years down the road too.

If you’re in B2B velocity sales like me, it’s normal to go through 5–7 demos a day. If you're not familiar with velocity sales, let’s break it down quickly.

Velocity sales refers to the comparatively short length of time (about 2-3 weeks) from my first engagement with a buyer to the final sale. SaaS sales cycles can be anywhere from a few months to over a year, depending on factors like complexity of technology and scale of decision-makers involved in the client’s procurement process. I’m often guiding over 30 prospects a week through a software evaluation, so needless to say I have days where I talk so much that my voice goes hoarse!

On a high level, software sales includes a discovery phase before presenting the solution via screen share demo. The discovery phase is all about finding out about the prospect’s business, the processes in place, and business problems or goals. Even during the presenting solution phase, it’s important to keep the dialogue going and sprinkle in questions for the client to ensure what’s shown in the demo is relevant to them.

During discovery calls, the recommended talk-to-listen ratio is 46:54. That’s almost 50/50—you’re not even selling a thing at this point! You’re asking questions and listening. During a demo on the other hand, the best talk-to-listen ratio is 65:35, so make sure you adjust for that.

You don’t want to get caught going into a decision call with zero idea of whether it’s going to close or not. How are you supposed to know though?

There’s a series of “mini-closes” that happen during the presenting solution phase of a sale. In order to achieve the “mini-close,” I’ll ask at least one open-ended question after showing one core feature of the tool. A few examples: a) “How does this compare to your current method?” b) “In what situation could you see yourself utilizing this feature?” c) “How could your team benefit from this feature?”

Not only do these questions facilitate dialogue and engagement, but you’re also forcing the prospect to provide constant feedback on which features of the tool resonate. The prospect is prompted to visualize this tool in place at their company.

Based on the answers to these questions, you can put together a mental tally of the prospect’s impression of the software. This information gives you a much clearer picture of the overall perception of the software and allows you to make a more educated guess about whether or not this deal will close.

Let’s say you’re asking those open-ended questions, but you’re getting short or one-word responses. You go, “So, how does this compare to what you’re using right now?” and all you get in reply is “Looks good!”. Or when you ask, “What specifically do you need to see before you sign off on this software?”, you get the response “I’ll know when I see it!”

You aren’t getting any combative questions or major concerns thrown your way.

In fact, they are going to make their hesitations known before signing on the dotted line. Ironically, these are buying signals. If your demo is met with intermittent “Looks great!” and “Cool!”, you may not have a serious buyer on the line.

With startups and innovative companies touting diversity and inclusion across the nation, this one is probably surprising.

The bottom line is that roughly 25% of salespeople in the tech industry are women and even less than that are in sales management (Fun fact: The incredible woman that wrote that Mashable article, Carolyn Betts Fleming, is the founder and CEO of the company that connected me to find my past and current sales jobs. If you want to find the best entry and advanced sales positions, I'd highly recommend checking out Betts Recruiting.)

I’ve had inspirational experiences from attending events intended for women in tech. These experiences include a fireside chat hosted by Emily Chang, author of Brotopia, and an event hosted by PowertoFly featuring women leadership at Slack’s SF headquarters. Typically I hear about these types of events at work or on LinkedIn, but if you haven’t come across one yet I highly encourage seeking one out if you’re a woman in tech!

I watched this TED Talk by Jia Jiang recently called “What I Learned from 100 Days of Rejection.”

He found out that the more someone gets rejected, the less it stings—so he set out to be rejected on a daily basis.

Given the pretty short sales cycle of the software I sell, I have over 50 open opportunities in my pipeline at any time. In non-sales jargon, that means I am helping ~50 prospective clients at a time determine whether or not to purchase Copper. This means I not only have 50 opportunities to win, I also have 50 chances to get rejected!

The amount of rejections you get really depends on your opportunity-to-win ratio, which is a metric used to quantify how many opportunities actually result in a sale. However, there are plenty of other ways I get rejected. Most AEs actually prospect for themselves, even if there is a sales development team under them. In order to set our own appointments, we’re constantly emailing and calling contacts who might benefit from a demo. Oftentimes, the answer on the other end of the line is “No, thanks.”

After years of being told “no,” I’ve come away with the most unexpected takeaway: rejection hurts less now, sure.

Even if it’s only once in a while. And that “yes” might be worth a hundred nos, especially when it’s revolutionizing someone’s entire business for the better.

The truths listed above are all the products of an Account Executive’s constant hustle—not just to reach quota, but also to achieve mutually beneficial, long-lasting business partnerships. I hope this post highlights the thoughtfulness that goes into consultative software sales, far from the pushy attitudes of salesmen from the wolves of Wall Street era!