Molly Shelestak

About Molly Shelestak

I spent 20 years as the person teams called when things were stuck, broken, or impossible-looking.At Google, I became the translator between engineering, product, and business. At Heap (now Contentsquare), I led the shift to a decoupled data platform — $2M+ in annual cost savings, 60× faster ingestion, sub-second queries across 3M events/sec. Then I did it again: cut another $2M/year in platform costs, launched an EU-hosted platform that generated >$1M in new ARR, earned our first ISO certification, and built a product team from scratch.I\'m good at making impossible-looking infrastructure problems ship.But here\'s the part that doesn\'t fit on a resume: while doing all of that, I built three businesses on the side. Not by sleeping less or hustling harder — by taking the exact same systems I used to ship at work (roadmaps, milestones, sprint reviews, accountability) and pointing them at my own projects.That\'s when something clicked. The system wasn\'t just mine. It worked for anyone who knew how to build but had never built for themselves.Now I do both. By day, I lead data platform infrastructure and data products at Contentsquare. And outside of work, I help senior tech employees ship the side projects they\'ve been sitting on for months — as a build partner, not a coach. Same systems. Same rigor. Just pointed at YOUR thing.What I bring to any room:→ Clarity when tradeoffs are complex and stakes are high→ Alignment across product, engineering, and business→ The ability to turn \"we should do this\" into \"it shipped\"Currently: Senior Director of Product Management at Contentsquare. Building \"Unstuck with Molly\"(build partnerships for side-project shippers) and Outli.ne (portfolio platform for visual creators).Previously: Google, SoftBank, Neustar, Andela.If you\'re a senior tech employee with a side project that won\'t ship → unstuckwithmolly.comIf you want to talk infrastructure, product, or impossible problems → mollyshelestak.com

Experience

1. Senior Director of Product Management

   Contentsquare

   Feb 2026 — Present

Education

• University of Florida

  B.S., Digital Arts & Sciences Engineering, Minor in Mathematics

  2002 — 2006