Work With Me

About

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, turning strategy into execution and ideas into real operating systems. Most of my background is in health-tech, but the problems I solve are not industry-specific. Early go-to-market confusion, messy handoffs, unclear ownership, and org structures that quietly slow everything down are common growing pains for leadership teams moving fast without a shared operating model.

I work at the intersection of go-to-market and operations. On the revenue side, I help teams find and build a repeatable commercial motion. On the operations side, I redesign how the company actually runs: how work flows across teams, who owns what end to end, and where the structure itself is creating friction. When something is not scaling the way it should, I help figure out why. What is 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. Sometimes it means redesigning how a company is organized once it has grown faster than its systems, moving teams off functional silos and onto a structure built around how value actually gets delivered.

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, and I work wherever I am needed.

How I Help

Operating Model & Organizational Design For companies that have outgrown the structure they scaled on, where functional silos, unclear ownership, and undefined handoffs are quietly slowing everything down. I diagnose where the operating model is breaking, then redesign the org around how work actually flows rather than around job titles. That includes reorganizing teams around the core pipelines that run the business, defining clear end-to-end ownership, building a director layer with real authority, and closing the white space between functions with explicit interfaces and handoff SLAs. I also connect operating decisions to cash, so structure and unit economics move together. The result is a company that can grow without every decision routing back through the founder.

Go-to-Market & Early Revenue 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 For companies where growth is creating more complexity than the organization can handle. I tighten execution across GTM, partnerships, and customer success, redesign the handoffs between revenue and operations so deals do not fall through the seams, and build the revenue operations systems that let growth scale without outpacing 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 the fundraising story, building board and investor materials, and coordinating across leadership. I also stand up and run advisory boards, from advisor selection to cadence and follow-through, so founders get real leverage rather than performative advice.

Special Projects & Interim Leadership For short-term, high-impact work where execution matters more than polish. This includes operating-model redesigns, GTM or organizational resets, new market or partnership launches, and interim leadership coverage during transitions.

Who I Work With

Founders and leadership teams with real traction who are navigating the shift from experimentation to scale, and need their operating model, go-to-market motion, and leadership execution to keep up.

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 operational and GTM 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? Get In Touch