5 Tips for Startup Sales Success From the World’s Worst Salesperson™ | by DC Palter | Mar, 2023

Founders have to do product sales even if they hate it

My personality is almost the stereotype of an engineer — I love working through problems to find the optimal solution but suck at building relationships. I can send you an email with the 10 reasons why you need my product, but I struggle to build an emotional connection that makes you want to jump up and send in your order.

In other words, I’m good at building products. I’m horrible at selling them. I’ve even been given the moniker, of which I’m quite proud, of World’s Worst Salesperson™.

But as company founder and CEO, I didn’t have a choice. I was responsible not only for company’s success, but for doing the actual sales.

After every painful sales call, I prayed to Ebisu, the Japanese god of trade and fortune, that the company would grow quickly so I could hire a head of sales to take over the selling.

I was sure that once we had a professional salesperson with the golden rolodex, a perfect haircut, and a natural ability to schmooze, new deals would flow like water and old ones would close quickly. Once I had that guy who could sell ice to Eskimos, we’d be unstoppable.

And yet, all 3 times when I got to the stage of bringing in a pro, sales not only failed to explode, but actually went down. Is it possible I wasn’t such a bad salesperson after all?

No, with all due modesty, I am truly the world’s worst salesperson™. But that’s exactly what an early-stage startup needs.

As I mentor new startup founders, especially scientists and engineers building hardtech products, I find I’m not alone. Nearly every founder puts hiring a salesperson at the top of their to-do list once they have funding. I think that’s a mistake. Because nobody can sell a product better than the founder, even if the founder is the world’s worst salesperson.

I don’t want to cast aspersions on all the great salespeople. They’re professionals doing a hard job. An unloved job. Is there any insult worse than calling someone a used car salesman?

Sales is a skill that takes dedication and training. Who really wants to be out schmoozing customers at Noma on the company’s expense account when they could be in the lab getting real work done? Not me!

But at the early stages until the product and marketing is ready-to-go, repeatable, and truly turnkey, it’s up to the founders to do the sales. Which is usually about 1–2 years beyond the time when the founders think the product is ready to turn over to a sales pro.

Why the Founder Has to be the Salesperson

If only we had a dedicated salesperson, we’d get more sales. If it’s commission-only, eat-what-you-kill, there’s no risk at all. Even if we have to pay a salary to get the right person, it will pay for herself. That’s the logic. It never actually works.

I get so many quarterly investor updates from startups that repeat the same story. They’ve been lucky to bring onboard the perfect salesperson and sales are about to explode. The next quarterly update includes an impressive sales funnel. The following quarter, the pipeline has grown to millions of dollars of potential orders, but sales remain disappointing. Some time around the one year mark comes the update that they’ve parted ways with the salesperson who wasn’t such a perfect fit after all.

What went wrong?

What was wrong? Well…everything. The salesperson’s job is to sell the product you have. Not design it. Not market it. Sell. Go find users. Get deals closed. Rinse and repeat. All day long.

But the product isn’t ready for that. Even if you think it is. Early sales is an extension of customer discovery — who needs it, what do they need it for, how are they using it? What gets them excited about the product? What causes them to tear out their hair? What’s missing that needs to be there, and what’s in there that’s getting in the way?

That’s not a salesperson’s job. It’s not how they think. They need to generate sales, get their commissions, and move on to the next customer as quickly as possible.

But customers aren’t biting. Yes, they’re interested in learning more about your innovative new product, so the pipeline looks impressive. But closing those deals is going to take more than the best salesperson in the world. It’s going to take time. Take pilot testing. And more iterations of the product.

Meanwhile, the salesperson is growing frustrated. They gave up a solid job with a big company in the expectations of getting higher pay and the chance of a huge fortune when those stock options pay off.

Despite your promises that the product was locked and loaded and ready to roll, they’re struggling to make the lease payments on their BMW. It’s time to go back to an established company again.

You may think the failure was a due to bad fit with the particular salesperson and look for a replacement. What was really wrong was your product wasn’t ready for a salesperson. And now you’ve lost a year and burned a lot of bridges with potential customers.

5 Tips to be Effective at Sales When You’re the World’s Worst Salesperson

I was actually an effective salesperson specifically because I wasn’t a salesperson. I was an engineer talking to other engineers. They appreciated that. Instead of being hounded to buy a product they weren’t sure they needed by someone who didn’t understand the product, we spoke a common language.

My goal as founder was more to understand their needs and make sure the product matched. I did more listening than speaking, and was honest about what the product could do now, what it would be able to do in the next release, and what the product wasn’t designed for.

I didn’t try to sell a product that would leave them disappointed. Short term, a sale is great but word gets out. Rather than trying to sell ice to Eskimos, I advised them not to buy my product if it wasn’t the right fit, then redoubled my efforts to search for the people who really needed ice.

So here’s my tips for how to be successful at sales without being a good salesperson.

1. Think like a customer: if the users are engineers, be an engineer. If the customers are data scientists, be prepared to discuss data science. If they’re bartenders, talk with them about the challenges of bartending. You’re one of them. You understand their needs and are building something to solve their problems, not just pushing whatever’s in your catalogue.

2. Be honest: Early iterations of the product have a lot of limitations. Be upfront about what the product can and can’t do. If you tell them it isn’t the right fit now, they’ll trust you when you come back later.

3. Be responsive: Ever try to buy a product from a big company? It usually takes weeks to get an answer to a simple questions like how much does it cost? If they ever reply at all. Respond right away with answers and you’re already way ahead of the competition. Be flexible about terms and willing to modify the product to fit their requirements and you’ll be their favorite salesperson ever.

4. It’s about customer discovery: Yes, sales are important. But your goal now is more about making the right product for the right customers than maximizing revenues. Listen to their needs instead of telling them why they should buy your product. Instead of “always be closing”, try “always be listening.”

5. Don’t try to be a salesperson: You suck as a salesperson so don’t try to be one. Don’t try to mimic sales techniques that won’t work for you. Frankly, most customers hate salespeople. Instead, be yourself. Be the innovator who wants to help them with their problem instead of a salesperson who wants you to sign a PO today so they can make quota.

Sales will always be frustrating, especially if you feel like you don’t know what you’re doing. Excited prospects will ghost you, your advocates will switch jobs, deals about to close will lose funding. It’ll feel like you’re doing everything wrong and someone else would do it better.

But nobody will do it better, because nobody else cares as much as you; nobody else knows the product as well as you; nobody else can change the product, the marketing, the company strategy to fit the customer needs like you. Only the founders can be effective at selling a startup’s products. Only the founders care about the long-term success of the business rather than getting a deal done today.

Which is why even if you’re the world’s worst salesperson, you’ll be better at selling your products than the world’s best salesperson.