As Segment grew from open source afterthought to the leading customer data platform, we "refound" product market fit several times. Surprising to me as a product person, our biggest learnings in PMF were from wildly uncomfortable questions from our sales team a thread 1/14

Our 2nd sales hire was @entrp4life, who we hired despite my protests to @RaphaelParker about a likely culture clash with engineering buyers. I couldn't have been more wrong. Not only did Surdi blow his number out of the water for years, but his customers loved him. 2/14

Clearly, I had something to learn here. I took the chance to travel with Surdi to visit customers all over the world. And every sales meeting, Surdi's questions made me wildly uncomfortable. How on earth was this working?? 3/14

Eventually, I started to notice the pattern. Surdi would open with something unexpected like "Why did you have us here today?" and follow it up with "Why is customer data a problem for you?" plus 10 other "why" questions including "Why don't you just build Segment yourself?" 4/14

It was awkward because... shouldn't we be explaining this stuff to them? But every question got the awkwardly off-balance & surprised customer to explain what their challenges around customer data were and share their deeper thinking and inclinations. 5/14

And then selling them was easy. It wasn't really even selling. We just explained how Segment the product fit into their problem and their approach. It was all backwards from how I noobishly expected sales to work. And it was phenomenally more effective, not just for sales. 6/14

It was also incredibly effective at learning what the customer's real problems were. Suddenly we could see much more clearly what our customers needed from our product. 7/14

It's no accident that a few months later we launched Segment SQL, which was our most explosive product market fit moment in the company's history. After that launch we grew ARR from $2.5M to $10M in 12 months and became cash flow positive. 8/14

I was just beginning to learn that sales "discovery" and "qualification" were like x-rays of a customer, hugely powerful for product development and product market fit search (and often clarifying for the customer too.) Later, this got 10x more structured and rigorous. 9/14

In 2019 @morrisseyjoe joined as our Chief Revenue Officer. Joe's first assessment was that we were wasting precious sales time talking to bad leads. I remember my eyes got big with panic at first, we're going to talk to _fewer_ customers?? 10/14

Indeed. And so Joe rapidly implemented MEDDPICC. A crystal clear method to qualify customers by not just asking Surdi's awkwardly powerful "why" questions, but also asking even more awkward questions like "Who's the ultimate economic decision maker on this? You?" 11/14

Again it was like a new product market fit superpower. You don't get anywhere by asking the easy boring questions like "What feedback do you have on my product?" You get somewhere interesting by asking hard-hitting sales qualification questions. 12/14

Now @CharmIndustrial, where I'm working on carbon removal and steel decarbonization, you might think this is all irrelevant. Hardly. We awkwardly ask Surdi's 10 whys and Joe's MEDDPICC of software companies about carbon removal and steel manufacturers alike. 13/14

...and it's in part thanks to learnings from them and the rest of the Segment sales team that Charm has found product market fit in both voluntary carbon removals and steel, and seen such acceleration over the past year. Thank you team! 14/14