Work With Me
I’m Diya Wadhwa Shah, founder of Henry Street Group.
For the past 14 years, I’ve worked inside high-growth companies alongside founders, operators, and commercial teams, helping turn strategy into execution and ideas into real operating systems. Most of my background is in health-tech, but the problems I help solve are not industry-specific. Early GTM confusion, messy handoffs, and unclear ownership are common growing pains, especially for leadership teams moving fast without a shared operating model.
I work at the intersection of go-to-market and operations. When something is not scaling the way it should, I help figure out why. What is actually working, what is noise, and what needs to change so the business can grow without compounding risk.
My approach is hands-on and pragmatic. I embed with teams as a fractional operator, project lead, or strategic advisor, depending on what the moment calls for. Sometimes that means helping founders get their first repeatable sales motion in place. Other times it means tightening execution across teams that have already grown faster than their systems.
Before starting Henry Street Group, I joined Zipdrug in its early days and helped scale the company through its acquisition by Elevance Health. I later served as Chief of Staff and Head of Partnerships at Photon Health, where I built sales, operations, and strategic partnerships as the company grew.
I tend to step in during the in-between stages, when the vision is right, the market is responding, but the operating model has not quite caught up yet. I stay until things feel clearer, more aligned, and built to last.
I primarily work with Seed through Series C teams building or scaling revenue, most often in health-tech and other complex, regulated, or founder-led environments. I am Brooklyn-based, but I work wherever I am needed.
How I Help
Go-to-Market & Early Revenue (Pre-Seed to Series A)
For teams with early product-market fit but inconsistent or founder-led sales. I help turn early signals into a repeatable commercial motion by clarifying positioning, shaping a practical sales approach, supporting early deals, and putting the right metrics and operating rhythms in place for the first commercial hires.
Commercial Scale & Execution (Series A to Series C)
For companies where growth is creating more complexity than the organization can handle. I tighten execution across GTM, partnerships, and customer success, and help build systems that scale so growth does not outpace accountability.
Fundraising & Board-Level Operations
For moments where narrative, metrics, and execution all need to line up. I support founders by sharpening operating metrics, refining fundraising stories, building board and investor materials, and coordinating across leadership. I also step in to stand up and run advisory boards, from advisor selection to cadence and follow-through, so founders get real leverage, not performative advice.
Special Projects & Interim Leadership
For short-term, high-impact work where execution matters more than polish. This includes GTM or organizational resets, new market or partnership launches, and interim leadership coverage during transitions.
Who I Work With
How I Work
I work fractionally or on a project basis, embedded with your team, with clear ownership and direct access to decision-making. This is for founders who want senior GTM and operational leadership without the commitment or risk of a full-time hire.
If you are at a point where misalignment or execution is holding the business back, I help you move forward deliberately and with less guesswork.
Interested in working together?