The Founder’s Dilemma with Sales

I’m not saying this happens all the time but I’ve seen it enough to think it’s worth writing about it. It’s when a founder (usually an engineer) starts a company with a solid product, gets a few sales/customers themselves early on, sees some traction and then hires a bunch of sales reps to go out and sell it.

Related: Founders: Before You Hire a Sales Team, Consider These Options

These sales reps inevitably struggle so the founder ends up cycling through VP’s and sales reps and then decides to invest in marketing automation to solve the problem. This may get them to a certain level but eventually they have to reinvest in sales to take things to the next level and they begrudgingly try to figure it out again. This is frustrating to everyone involved: the founders, investors, sales teams, and clients.

Related: Using Sales Conversations to Find Product-Market-Fit

So why does this happen so frequently?

In my opinion, there’s one main reason – passion.  When a founder comes up with an idea or creates something new, they’re obviously very passionate about it and rightfully so. The first people they usually approach with the idea are their friends, family and people who know them.  When they passionately explain what they’ve developed to a friendly audience they usually get very positive feedback. Some of these people may actually even purchase the solution which provides validation.

Based on this, “sales” seems relatively simple to the founder so instead of mapping out a real strategy and investing in sales they decided to hire a bunch of sales reps to go sell it.  The problem is that sales reps inherently aren’t as passionate or knowledgeable about a product or a solution as the founder is. They may try their best but the sales don’t come as easy without that passion and innate knowledge.  

Someone once told me that “sales” is the transfer of enthusiasm. I truly believe this and think that the number one thing you need to be successful in sales is a belief in what you do. Since founders obviously believe in what they do, that transfer of enthusiasm comes easily to them.  Not so much for everyone else.


This exact scenario happened to me with my first start up company. A good friend of mine started an IT services company and I came on board to run sales. I knew nothing about IT so I would go on sales calls with him. He was very passionate about what we were doing and it came across in the meetings. I vividly remember coming out of a meeting with a prospect that went really well and as we were walking to the car he said “I don’t know why everyone thinks sales is so hard. Everyone needs what we have. All you have to do is find the right people to talk to.”  

I remember thinking to myself – thanks for shitting all over my profession and minimizing everything it took to get that meeting, and everything it’s going to take to close it from here. The meeting is by far the easiest part of the sale. Unfortunately, this is usually the only part of the sales process that sales support (engineers, exec staff, etc.) are exposed to, which may be why it doesn’t seem that hard. Real sales is done in the trenches before and after the meeting.

Founders need to understand that the gap in passion between them and the people they hire, is a real issue, and sales is a group that needs it more than most.  Sales also can’t be an afterthought or a necessary evil.  If you don’t create a sales culture from the start with everything aligned to help support sales it will be a struggle and you’ll only get so far. You can have the best product in the world but if you can’t sell it, it doesn’t matter.  Ask any venture capitalist out there – one of the main reasons most companies fail is because they can’t sell.

With this in mind, here are a few tips for founders:

1. Have a clear vision and live it every day.

2. Make sure the reps know exactly how they fit into that vision and what they can do to have an impact outside of hitting their numbers.

3. Review your onboarding process and have a heavy focus on getting people bought into the vision of the company and the difference you make for clients.

Example: I used to give new reps a blank org chart with only titles and they had to go find the people with the titles and interview them. They had to treat it like a sales call with prep and specific questions focused on understanding why that person worked at the company. Then they had to put together a one-page summary of what they learned.

4. Make reps read all your case studies as part of the onboarding process and get familiar with telling those stories.

5. Allow new reps to go out and meet with clients to understand the value they bring to the right customer.  

Sales reps – sell what you believe in.

As a rep, if your leadership hasn’t transferred that enthusiasm to you, go seek it out and ask for it. I promise you that no leader will ever turn you down if you’re seeking to learn how to be more passionate about the business they started.  If they do turn you down, then go find another company to work for.

When I was fired after my IT service company was acquired I went through somewhat of an identity crisis. I had been an IT sales guy for seven years and hadn’t thought of doing anything else. I wondered if I was destined to be an IT sales guy for the rest of my career. The problem was I didn’t even really like IT or computers that much. My wife is the one who got me to think about my career and why I had been so successful at each of my previous roles.

Why was I one of the top reps at DeWalt? Because DeWalt power tools are badass. Why was I one of the top reps in my region at Xerox? Because, at the time, I believed Xerox was the best in the industry. Why was I so successful at the IT services company we started? Because I believed in the people I was representing and knew they would do an incredible job for our clients. It got me to realize that it didn’t necessarily matter what I was selling, it mattered whether or not I believed in what I was selling.  

Go find your passion for what you do and then transfer that enthusiasm to make it happen.

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