Tips for Founders Doing Sales (From a Founder)

> Don't promise features you are not planning to build and align your prospects expectations with.

As an engineer turned sales for my own indie company (15 employees today, had 0 when I started doing sales) - I partially agree with this point.

Don't build something custom simply to win a new customer. But there are a few times I've listened to a prospect describe their need and I though, "huh, that kinda wasn't in my original vision but it could be useful to other customers/markets." I'd subsequently tell them the feature is on the roadmap and pitch a higher price than I normally would.

Sometimes they bite, sometimes they don't. But on a few occasions, they came on board, I delivered, and that feature became a popular differentiator with other prospects.

This is indeed a hard lesson to learn. For me I used to charge less out of insecurity that I will lose the customer. But later on I grew some backbone to ask more. It depends on customers as well. Now I simply steer clear of prospects too driven by price rather than value.

The first customers were definitely the hardest. I didn't do any classic marketing, just cold calls and emails. It took a few months to get the first paying user. I did target a specific niche.

I then went in a road trip around the northeast (literally camping in a tent at the nearest KOA or park) hitting different areas where customers were. I'd stop in town, call them up, and tell them I was passing through (which was kind of true) and ask if they could meet for a half hour. I got some of my first meetings that way.

It was extremely inefficient but helped grow the initial user base. It's definitely not an approach I'd recommend to someone - it's kind of ridiculous but it worked.

That said, the customers I was targeting were all part of the same trade association and the word spread that I was actually doing something pretty useful. That led to new customers and a lot of word of mouth.

I only seriously started with traditional outbound marketing this year, which is my 8th year in business. Other than that it's been direct outreach, word of mouth, and attending conferences and drinking my ass off with potential customers (not ideal, but every association has its own vibe and sometimes you gotta do what you gotta do).

Building partnerships with like minded entrepreneurs in your industry is a good approach too (referrals, integrations, etc)

All this said, it took 4 years to make enough money to pay myself and 5 years to hire my first employee which was a customer support manager. "Delegating and elevating" is magic and led to more time to focus on growth. I did a lot of freelancing in those first 4 years to make ends meet. It could definitely be done faster, but I was way more of a n00b than I realized at the time (isn't that always the case?)

Sales is easy if you're rich and connected;

One of the best tips I received for sales: when trying to sell a pen, don't focus on the features. Stop and ask the customer - what are they looking to do with a writing instrument? Go as deep as possible in understanding their need in that conversation by asking questions. Once you understand the need - work out how best to fit the pen you're selling to their needs.

Two benefits of this approach: the customer does most of the talking. And by listening intently you know the things to say to help the customer see what you have matches their need.