Jeff Gray COO and Operating Partner to Founders

Jeff Gray

Services

I'm an operator who builds. I join B2B technical companies with a product that works and growth problems to solve, and I build the operating system that lets them scale. Increasingly I ship software rather than spreadsheets.

Scaling go-to-market

"We've got two sellers but think we're ready for five or thirty"

Making cross-functional processes work

"Sales, finance, and ops each have a version of the truth, and quarter-end is a fire drill"

Company planning, sales comp, growth strategy...

Building an operating plan

"Where should we spend our money and how long will it last?"

Interim and fractional CxO

"Omigod this key exec in GTM or finance left or went on parental leave"

You can engage me in three primary ways:

Series A to Series D in a box.

About Me

As a consultant, I led finance at c1.ai through diligence and its agreement to be acquired by Workday, and rebuilt its FP&A and commissions processes as software along the way. I've also been the fractional finance leader for three other startups in the past year and rebuilt pricing for multi-year, complex clinical studies at Picnic.ai, where my custom app now runs with no engineering support.
Before that, I was Chief Operating Officer at Honeycomb, growing the company from under $5m to well over $50m ARR and raising ~$100m.
  • Owned the full operating model: GTM strategy and execution, all corporate functions, business planning and management.
  • Took on CRO (2023) and CMO (2024) responsibilities as well.
  • Interim CEO during the founder's parental leave.
  • Managed board and investor relationships.
I ran business operations and day-to-day execution at a data science startup and an infrastructure startup for two years each. Each time, I partnered with the CEO on managing the board and raising growth VC rounds, leading one to the doorstep of its successful acquisition.
I spent the first 16 years of my career at ThoughtWorks, the global software consultancy. I started as a novice developer, ran software development teams all over the world, and led a 600-employee, $200m P&L, the company's largest, by the time I left. ThoughtWorks was where I grew up as a professional. While it feels so long ago, it's where I learned how fast feedback loops are the most important thing in technology projects, where I learned how to treat people and build inclusive teams, and where I learned from the best managers and mentors I'll ever have. I try to live up to their examples every day.

Sometimes fractional work turns into something bigger. I'd consider a President or COO role with a founder I trust, at a B2B technical company with a product that works and growth problems to solve. Working together first is the best way for both of us to find out.

I live in the Potrero Hill neighborhood of San Francisco. I enjoy cycling around the city to work with people in person and collaborating remotely with folks anywhere in the world.

Resources

FP&A Agent

A set of Claude Code commands for people who build financial plans.

Planning for Startup Founders

Why and how to try to predict the future for young companies.

How to OKR

The only thing worse than doing OKRs is not doing them.

Contact

Prefer to talk directly? Book a call — or send a message below.