Engineering Leadership · Lead / Manager / Head of
Nothing I build needs me in the room.
Leadership, as I practice it, means building the conditions where the team ships whether I am there or not. I have done it as a staff engineer inside other people’s orgs, as the owner of a whole business, and as a founder raising on the strength of what the team shipped.
Leadership with a P&L attached
People, visibility, and business outcomes, each with a number.
I owned and ran a full-service steakhouse. Hiring, training, scheduling, vendors, costs, and margin were all mine. I now lead software teams with the business math in mind, because I have personally signed the checks the math describes.
At Cloaked I built the product-analytics stack that taught the company to make data-driven calls, then a cross-functional ideation portal so design, product, engineering, and the executives shared one transparent view of the work in flight.
At CyberGRX I redesigned the build and deploy process and had every engineer trained and shipping with it inside 3 days. At Inception Health I mentored product and mobile teams on CDK, serverless, and CI/CD until they ran their own platform.
I cofounded Ravi, an agent-native SaaS, carried the product end to end from prototype through the Apple App Store, and raised a $400K pre-seed from South Park Commons on the strength of real usage data.
My first 90 days with your team
The same three moves every time, with a receipt behind each one.
Make delivery easy
I find the slow, error-prone parts of shipping and rebuild them into tools the whole team actually uses, even as AI floods the pipeline with PRs.
CyberGRX went from quarterly manual deploys to shipping on demand. At Food Service Warehouse, teams on my infrastructure ran the company’s fastest release cycle.
Bring visibility to the team’s work
I get real metrics in place so decisions stop being guesses and everyone can see what’s actually working.
Built the product-analytics stack at Cloaked that taught the company to make data-driven calls, then an ideation portal that gave the whole org one transparent view of the work in flight.
Ship the small first version, instrumented
I put an embarrassingly small v1 in front of real users with tracking from day one, then let how they use it decide what’s next.
Ravi started as an embarrassingly small instrumented v1, and its real usage data is what won its $400K funding.
“Jake is a force for good unlike any other. He migrated our infra to a cheaper and more scalable system, crafted a CI pipeline that accelerated deploys by 30x, and taught the whole company how to make data-driven decisions by building an entire product analytics stack. And that was just his first 6 months.”
Aaron Biller, Director of Platform Engineering, Cloaked
“I watched Jake redo a build and deploy process over the span of 3 days, whip up a presentation, and get every engineer in the org up to speed using it, a moment I’ll never forget because our productivity EXPLODED afterwards.”
Stephen Bapple, Software Engineer, CyberGRX
Sound like the role you’re hiring for?
The resume has the full 15-year history. Or skip straight to a conversation.
Or browse my projects & ventures. Screening with an AI assistant? Point it at ai.jakegaylor.com.