Senior · Staff · Engineering Leadership
I make good teams ship like great ones.
Good teams rarely lack talent. They lack speed, focus, and the visibility to see what’s working. That’s the gap I close, fast.
What changed after I showed up
The real outcomes teams measured after I joined.
“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.”
Software Engineer, CyberGRX
Protectwise’s product teams never had to ask whether the backing systems would hold. I built the infrastructure ahead of their scale and kept it boring: thousands of Cassandra nodes, petabytes in S3, $10M+/yr of production AWS.
My role: Senior DevOps Engineer, Protectwise
“We were deploying C# on vSphere when Jake joined our first Node.js team. He brought Docker, we moved to Kubernetes, and our services had the fastest release cycle in the company.”
Architect, Food Service Warehouse
“Everyone else told us how to work around problems. Jake built us better tools.”
Operator, Magic
Whatever you’re short on, I’ve shipped it
My core is delivery: making teams ship fast and see what’s working. 15+ years across many related disciplines have made me fluent in most and genuinely deep in a few.
SaaS & AI Products
Spent my career building SaaS, lately deep in AI: LangChain agents at Cloaked, the framework behind Block Party’s internal coding bots, Ravi, an agent-native SaaS for secret management, and Fountain, the control plane that runs my own fleet of sandboxed coding agents.
SRE & DevOps
Ran SRE on petabyte-scale systems at Protectwise, through dozens of production deploys a day, and across multiple lines of business. Off the clock, same discipline: a GitOps-run k3s cluster serves production from my house.
IoT & Firmware
Designed custom air-quality sensor PCBs, wrote their firmware, and built the SaaS that drives it all to a target climate. Deployed across a controlled-environment agriculture facility: 100 control units and 200+ sensors.
Business Ownership
Ran a full-service steakhouse outright: hired and led the team, drove $500K in annual revenue, and owned the vendors, the costs, and the margin. Now I build software with the business math in mind.
My first 90 days on your team
Anyone can claim they can build. Here’s what I actually do in the first three months, with a receipt behind every move.
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, so design, product, engineering, and the executives shared 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, the agent-native SaaS I founded, started as an embarrassingly small instrumented v1, and its real usage data is what won its funding. Fountain, my agent control plane, was largely built using itself.
Hiring for a senior, staff, or leadership role?
If your team needs someone who can lift the whole team and build at every layer, let’s talk.
Or browse my projects & ventures, or tour the homelab. Screening with an AI assistant? Point it at ai.jakegaylor.com.