How PMMs find Product-Market Fit

This case study was created from an episode of the Product Marketing Adventures Podcast. It has been adapted into Dusted's case study format to preserve and showcase the guest's real-world experience. Written to preserve the voice of the true author, Pranav Deshpande.

Finding product-market fit is one of the hardest things a PMM will ever do—and knowing when you don’t have it is even harder. I’ve seen both sides across my career. At Twilio I worked on high-scale messaging and developer-first GTM after the company had already achieved insane PMF with SMS and voice; they went public within a year and a half of my joining. I later joined the early Autopilot team (an NLU chatbot/voice-bot API in beta, pre-LLMs, around 2019). After Twilio I became the first marketing hire at Modern Treasury (~14 people), built the product marketing function over two years while wearing every marketing hat, and faced the challenge of creating narrative and demand in a new FinTech category. Now at OpenAI I help define GTM for the API platform and frontier AI products that developers and enterprises use to build new businesses.

At Twilio Autopilot I carried over the mindset from SMS/voice PMF and didn’t sufficiently question assumptions. We had massive distribution and customer interest thanks to the Twilio halo—no shortage of pilots, especially in contact center and customer service—and the ROI story plus programmability looked strong versus legacy tools. The real problem was core product and underlying tech: the models required heavy hand-holding and hard-coding, were orders of magnitude less capable than even small modern LLMs, and the low-level customizability made flows brittle and created a barrier past initial trials. It wasn’t messaging or distribution; it was product readiness and form factor.

At Modern Treasury the first customers (startups and a few larger logos) came through founder sales, word of mouth, and VC networks. What I didn’t examine critically enough early on was whether those paying customers were acquired and using the product the same way. The business model was untested: a two-sided (effectively three-party) motion requiring the customer, Modern Treasury, and a bank all to align so companies could run cheaper/faster B2B payments on bank rails. We effectively had ~20 different ICPs across a few dozen deals. Product risk felt secondary (strong eng team, great demos); the bigger issues were business-model and market risk and the absence of repeatable sales.