“People buy from you not because they believe you have a great solution – they buy from you because they believe that you understand their problems.”

These are words that have followed Dominic Caposelli since he heard them from an executive sales coach in Minnesota.

Now living in New York City, he is managing partner of client development firm JJELLYFISH, where he oversees startup engagements.

After 13 years working in enterprise sales, he has seen his fair share of founders who succumb to the anxiety of selling your dream.

“Sales is not about me convincing you to buy. It's a mutual fact-finding mission to figure out if our solution fits your needs. And when you think about it like that, your job is just to uncover that and 'no' is an OK answer,” his mentor once told him.

By seeing things from this angle, it can take the pressure off of founders. But, he advises, entrepreneurs need sales tactics to come naturally. “They've literally built a company based on solving this problem, so they should be obsessed with understanding whether folks have it.”

“Every product ultimately solves a problem with the status quo,” he highlights. “And trying to understand that pain deeply to figure out if your solution is the right one is the essence of sales.”

DO NOT OUTSOURCE SALES (Yet)

We see that founders pretty consistently are not great at sales. They don't have that skill set. They're busy and sales is very time-consuming. It seems like such an easy decision to outsource.

What they end up doing is hiring someone like me – a vice president of sales or a more junior level – and say, “hey go figure out sales.”

The vice president of sales is really good at the latter side of that growth, which is scalability. They're great for a company with a product-market fit – being able to plug in the right pieces and manage that.

For technical founders, I’d advise they not outsource the sales process. They need to be active and involved. Our whole product is about pairing with them to help with skill sets and then get closer to a product-market fit quicker.

So when we think about that repeatability piece, the founder really needs to be directly involved. They need to be the ones who are selling. They need to be the ones who are in every single conversation. 

And they really need to be focusing – not just on showing the product – but understanding the problem with the status quo.

Unique Needs

So what's really important is that a founder has a unique point of view on why the way the world works currently.

So how does that founder find people who are dealing with that challenge? Sometimes it's personal experience. Sometimes it's word of mouth. Sometimes it's just a theory. So founders need to meet with people who own that challenge to understand how it is manifesting – or if it's even manifesting for the prospect.

I think that's a part that gets kind of underappreciated. Most founders want to talk about their solution and the value it brings versus trying to understand first: does the market even care about solving the problem that you think is so important?

That's why the founder has to be involved in any kind of early sales conversations, because what they're going to learn in those conversations usually leads to five or six pivots before they actually get to a repeatable motion.

Effective sales strategy is critical because founders must personally shift focus from their solution to the customer's problem to achieve initial feasibility. This hands-on approach is essential to build a repeatable sales process before a company can scale.

Stop Guessing, Stay Flexible

One of my biggest pieces of advice for an early founder is to be flexible, because very rarely is the company that you set out to build your company for a market and the value proposition, but those plans almost always change.

Your job is to basically be a conduit for the information that you're getting and then make the little tweaks every single day to be successful. Those changes – and from a sales perspective – means understanding and actively listening while remaining being problem-focused.

The foundation of being a great salesperson is to be a great interviewer and great listener. Research shows the best salespeople spend only 30% of a conversation talking, while the worst are talking for about 65% of the time. It's in that 30% where you're actively listening, fully diving in on someone and trying to understand what their current situation is – that’s when you're most successful.

People get really caught up in things like a closing method, so, like, don't worry about specific tactics. Worry about becoming a really good active listener and focus your energy there.

Ultimately, sales is one of the few jobs where you can make more money the more emotionally intelligent you are.

The more you can sit in the room and understand what's happening, as well as in the dynamics of that conversation, the better off you're going to be, because it's ultimately about people and understanding where they are and what they're about.

‍