PITTSBURGH, PA · OPEN TO RELOCATION

I translate fragmented, expert-heavy problems into products that ship, scale, and exit.

Over six and a half years at UPMC Enterprises, I turned unfamiliar domains, clinical workflows, cognitive care, chronic pain, into products that ship, scale, and exit.

Debashish Sasmal
THE PATH ·

A decade in engineering roles before venture leadership at UPMC Enterprises, plus guest lecturing at Carnegie Mellon's MS Product Management program and co-hosting The Product Signal.

// THE PROOF

Three ventures, the same method.

Regulated healthcare, an EHR-scale investment, a venture built from zero. Different bets, same pattern: find the real constraint, then re-architect around it.

// HOW I LEARN A DOMAIN

I don't start with the product. I start with the room.

Rapid domain acquisition is the skill that lets me move between markets. Here's the sequence I run every time.

01
Map the experts and their incentives

I learn who holds the knowledge, who decides, who pays, and who quietly blocks. In expert-heavy markets, the org chart lies and the incentive map doesn't.

02
Hunt the constraint, not the feature

Almost every product I've shipped won because I found the real bottleneck (specialist time, onboarding friction, a broken handoff) and built against that.

03
Write a thesis I can be wrong about

I put a falsifiable thesis on the table early and let domain experts stress-test it. The fastest way to learn a market is to be wrong in front of people who know better, then fix it.

04
Decide build / buy / partner from the thesis

Once the constraint is clear, the path usually is too. My job is to make that call honestly, even when it's inconvenient for the org's default.

// THE THROUGH-LINE

The constant was never a domain. It was a method.

Same method, three markets: CRM data, real estate, and six years in regulated healthcare, where the stakes and the expertise run deepest.

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// EXPLORE

// WORK

Case Studies

Three ventures across digital health: the bet, the call, and what it proved.

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// AI

AI Builds & POV

A point of view on AI in regulated products, backed by things I actually built.

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// ABOUT

Who I Am

The through-line, the method, the podcast, the teaching, the track record.

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// CONTACT

Let's Talk

Building something ambitious in a hard market? That's the conversation I want.

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