The Top Misconceptions in Startup Sales, Episode 4
Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the next few months, in the form of weekly episodes, we’ll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you’ll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here’s your fourth installment. Read on.
“My product will sell itself once I demo it.”
I’ve seen this belief permeate Startup Land. “We’ll just book a lot of demos, show our product off to prospects and then ask them to sign on with us. Done deal!”
That’s just not how sales works. Or sales processes for that matter.
Flash back to early 2014. At Whitetruffle, we had just overhauled our business model; transitioning from a contingency fee-based shop to a SaaS company. My close friend & CEO Alex had handed me the keys of the customer-facing side of the business. And I was tasked with figuring out how we’d build our new sales model. I went to Mike, one of our cofounders, for advice. “Paul, I don’t think we’ll have a big enterprise motion here. You might not even need to demo the product.” Mike is a mover and shaker in The Valley, as founding partner over at Riviera. I had never designed a sales process from scratch. Armed with a 14-day credit card activated free trial, I aimed to keep things simple.
We installed a 15-minute qualification call with new prospects. After qualifying them, and getting them excited about our product, I’d tell folks, “Sounds like there’s a fit here. Why don’t we get you started with a 14-day free trial? It’s credit card activated, so you’re going to have to enter your credit card. We’ll be monitoring your account. If anything pops up, we’ll reach out to address it together. And if any issues arise on your end, please feel free to reach out. We’re always happy to help.”
Click. Prospects left the call excited at the possibility of testing out our tech talent sourcing platform. I could hear it in their voices.
And yet, guess what ended up happening?
Of all the folks that had both been qualified and committed to trialing Whitetruffle, only about a third of them would actually create trial accounts.
I couldn’t believe it.
These folks had expressed their pain to me on our qualification calls. They needed our software to help them source candidates, so they could build out their tech teams. And yet two thirds of them weren’t following through.
‘What the hell is going on? They want our product. Why aren’t they starting free trials?’ I kept asking myself. Dumbfounded, I banged my head against the wall for weeks.
Then, a solution came to me. Mostly out of frustration. ‘If these folks aren’t going to start these trials, we’ll install a forcing function to make them do so’, I thought to myself. With that, we installed a trial onboarding call. Dubbed “Account Optimization Call”, it sounded a bit fancier and more value-laden. We sold it to prospects as a way for us to “ensure that you’ll be onboarded properly to our platform and make the most of your 14-day free trial and beyond.”
Overnight, everything changed.
We went from having only around 33% of our qualified prospects converting to a free trial to nearly 100%. Interestingly, about a third of prospects would now show up to this account optimization call a little frazzled, apologizing for not having entered their credit card info and starting their free trial. I’d tell them, “No worries whatsoever. We’re scheduled for thirty minutes today. That’s more than enough time. If you have to go get your CFO’s credit card right now, no problem. You can also enter yours. And swap it out later if need be.”
We finally had our backstop to get prospects doing what we needed them to do. The hemorrhaging of opportunities had stopped. And our sales were off and running.
A hard realization was also sinking in: human beings don’t do what they’re supposed to do.

Yes, as a salesperson, you might be within a prospect’s top five priorities while they’re on a call with you. Family, Faith, Friends, in whatever order they might have them. Then perhaps you: the seller. After all, you’ve got their undivided attention. But when the “End” Zoom button is pressed, you’re likely to slide down that list. Fast. Their dog gets a case of indigestion and needs to be taken to the vet. Their kids come home with a project that needs to be completed by the next morning. Only twenty four hours later, you’ve likely slipped all the way down to number 19 on their priority list. Unintentionally. Without installing forcing functions to control the sale, you run the risk of deals stalling or dying outright.
Back to our original premise. Sales don’t get generated just through demoing. Yes, a product demo can be an integral part of a sales process. But we build sales processes to take our prospects through a journey that maximizes our chances of closing them. We also need to do things like qualifying, conducting discovery, obtaining the buyer journey, sharing commercials, and obtaining a verbal close. These sales fundamentals are all part of controlling the customer conversation.
Building a successful sales process takes experience, intelligence, curiosity, and humility. After putting together the initial version, you’re going to want to battle test it and refine it based on the feedback you’re getting from the market.
And between these steps in the sales process, you’re going to need some connective tissue. The reason why our Account Optimization Call was such a hit is because we made it feel valuable to the prospect. We sold them the next step. And with that, they not only agreed to get it scheduled, but they showed up in large numbers. It’s not enough to build and refine a sturdy sales process, you’ve got to work on the transitions between stages. Those that know me in a sales context know how much I preach for selling next steps. Without it, you run the risk of massive leakage in your funnel.
Exhibit A. Our first sales hire at Whitetruffle was Chris. A student of the game (I knew I’d recruited the right person when “Fitz” handed me a copy of Challenger Sale in his first few days on the job. A book I devoured over a long weekend). The man is conscientious. After onboarding him as best I could onto our newly minted sales motion, Chris got in front of customers. A few weeks in, Chris astutely came to me with an issue: massive drop-off in his funnel post-intro call. Folks were willing to schedule the Account Optimization Call, but he was getting a lot of no-shows. As I listened to the way Chris was selling the next step at the end of the intro call, it didn’t take long to unearth the root cause.
Chris wasn’t yet fully articulating the value contained in our account optimization call. When prospects were seeing it pop up on their calendars, they probably couldn’t recall there being something in it for them in the upcoming meeting. And thus would not attend. After a bit of coaching – the guy is a quick study – Fitz became assertive in conveying why it was in the prospect’s best interest to attend our trial onboarding. His show rates rose up fast to above 90%. And his sales funnel was now patched up and humming on all cylinders.
The moral of the story?
It’s great to have a well-designed sales process. But without sturdy connective tissue between its steps, you’re running the risk of draining your pipeline of deals.
So next time you hear a founder tell you they’re “just going to schedule loads of demos with our ICP, showcase our cool new AI product, and have them sign up with us right away.”
You’ll know to say, “Hold your horses, Cowboy. How’s your sales process? How are you going to control the sale? To make sure prospects stay engaged and on tracks to becoming a paying customer?”
Next week, we’ll examine why it’s rarely too early to kickstart your go-to-market.