How I learned to stop worrying and love indie sales
Here’s some advice: Don’t go into indie consulting if you don’t love sales. And here’s some more: Don’t decide you hate sales until you’ve really tried it.
Now that I’ve tried selling in earnest, I love it. But when I was considering going out on my own, I dreaded the idea that my livelihood would depend on my abilities as a salesperson. The prospect of doing sales was my number one hesitation. I was bad at it, I told myself, and worse yet, I didn’t enjoy it. Not a great combination.
I’d done a bit of product sales, and I’d managed salespeople, but I’ll be honest: I found sales cringe. Lead gen, cold emails, qualification funnels, forced conversations, awkward start of call chitchat, constant rejection, pushiness, framing tricks, price negotiation, and repetition, repetition, repetition? No thanks. (I really admired the folks I managed, though. Truth be told, I envied their confidence.)
What I know now is that selling services is totally different from selling products, and selling at the individual level is totally different from selling at the company level. The things I need to do well as an indie consultant bear only a passing resemblance to the things a product sales team needs to do well. In indie consulting, you’re selling yourself. You might have standardized pricing or a few packaged options, but ultimately they’re buying you. You’re not selling a solution, you’re selling a belief that you will be able to find an implement the solution. That gives you so much more room to listen and adapt.
The breakthrough came just before I decided to make the leap to indie. In fact, the breakthrough caused the leap. I had a hunch that I’d be valuable to founder CEOs of relatively young companies. To validate the hunch, and decided to go on a research sprint: One month, as many conversations with these founder CEOs as I could manage. Thankfully I already knew a few, and friends knew a few more, so I was able to have about ten conversations in the month.
Here’s the email I sent:
Hi ___,
A small favor to ask: Any chance you'd be up for a 15-minute call in the next couple weeks? I'm considering going independent and offering myself as an embedded exec for 3- to 12-month stints. Still trying to work out what this would look like and where I could help, so I'm talking to as many founders / CEOs as possible before committing to the idea. This would truly be 0% sales and 100% research, and if you can't squeeze me in, no worries at all.All the best,
Andrew
Every person I emailed said yes and the conversations were a delight. I asked about their business model, their leadership team, the gaps they had, the competitive landscape, their customer segmentation, their go to market motion, their analytics capabilities, the conversations they couldn’t have with investors, and on and on. All of them ran well over the scheduled time because we were really getting somewhere.
Though these conversations truly were 100% research, I had unintentionally stumbled into an approach that would form the foundation of a repeatable sales process. Those foundations:
Warm intros
Founder-focused
Intensive discovery
Highly personal
Highly collaborative
By the end of each conversation I knew whether I could be helpful and how. Conveniently, the founders knew too. Just from the questions I asked and the back and forth that followed, several of them decided they wanted my help. “These were great questions — when can you start and what do you charge?”
That was all I needed to hear. The research sprint validated some pull from the market. Potential customers told me they wanted to buy what I was selling — even though I had told myself I wasn’t selling it yet.
And in the process I learned to love sales. No more existential dread about turning into a “sales guy.” Instead, going indie was an opportunity to lean into my persona as an “inquisitive guy,” and that was something I could get excited about. A month later I’d left my job and was out on my own.
I’ll link to Part 2 as soon as I have it, which will cover what my proper sales process looks like now.