I recently sat down with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital. As someone who leads product teams and thinks deeply about product-market fit and go-to-market, I was eager to unpack the 0 to 1 thinking behind Persona’s trajectory.
Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. For anyone operating in B2B SaaS, that’s the kind of signal you can’t ignore.
In our conversation, one theme stood out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, he brings this mindset to every aspect of running Persona. I share that instinct — when we anchor on “why it won’t work” early, we surface edge cases, stress-test assumptions, and prioritize outcomes over output. It’s a product discovery discipline that keeps teams honest and accelerates product-market fit lessons.
Rick also shared counterintuitive practices that resonated with my own founder-led GTM experiences. His engineers sell and cold-email prospects, and he doesn’t try to convince candidates that Persona is a company that will change the world. That may sound unconventional, but it’s exactly the clarity zero-to-one companies need: tight customer feedback loops, direct exposure to objections, and authentic hiring that screens for fit over hype. In my experience, these choices reduce handoffs, sharpen messaging, and create a culture that learns faster than the market moves.
There’s a broader leadership lesson here for product management: treat pre-mortems as a muscle, not a meeting. I apply this to hiring scorecards, roadmap bets, and go-to-market plays — explicitly listing failure modes, customer objections, and “anti-personas” who won’t buy. When we teach engineers to engage customers directly, we’re effectively building forward deployed engineers who carry context from discovery to delivery to launch, closing the feedback loop and improving zero to one B2B marketing execution.
For founders, engineering leaders, and hiring managers, the takeaways are practical: start with the “won’t,” design for objections, and let builders meet buyers early. Pair this with a clear definition of success metrics and a bias for candid, frequent iteration. The result is a stronger compass for product management leadership and a far more resilient go-to-market motion.
You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/
Inspired by this post on First Round.
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