Engineering Leadership · Lead / Manager / Head of
Teams I lead ship faster and can prove it.
I have led as a staff engineer inside other people’s orgs, as the owner of a restaurant, and as a founder raising on what the team shipped. My job is clearing what slows the team down, putting its results where everyone can see them, and keeping releases small and instrumented so product has real numbers to steer with.
Led from three different seats
Staff Engineer, Restaurant GM, and Startup Founder.
I owned and ran a full-service steakhouse, everything from hiring and scheduling to vendors and margin. Seven people, no two of whom needed the same training or the same patience, and I had to learn each one. I still weigh every engineering call against what it costs, and people are the biggest line.
At Cloaked I built a cross-functional ideation portal so design, product, engineering, and the executives worked from one board of the work in flight, from idea to usage reports. Nearly everyone in the org used it, and an exec’s idea and an engineer’s idea looked the same inside it.
At CyberGRX deploys were a quarterly, manual event. I redesigned the build and deploy process, presented it to the org, and had roughly 50 engineers across several teams trained and shipping with it inside 3 days. From then on they deployed whenever they wanted.
I have founded three startups. At SocialDrizzle I ran engineering and product with a team of peers fresh out of college, and learned to set expectations out loud and get everyone to agree to them before the work started. At GrowBuds, three founders and a hardware product meant a million moving pieces. I kept the team taking small steps forward through the hard stretches, and made time to look back at the ground we had covered.
How I run a team
Each with the receipt behind it.
Agree on the standard before the work starts
When a team forms, we agree on how the work gets done and what good looks like. New hires hear those expectations out loud, even though they will see them modeled by their teammates. When someone falls short, they know how it lands on the team, and any conversation about training, remediation, or letting go has something to stand on.
At SocialDrizzle I ran engineering and product with peers fresh out of college. Once we had agreed that perfect is the enemy of good, saying it again kept everyone moving. Without the agreement, it would have sounded like a manager asking for less than their best.
Learn each person
The work runs through people with lives. By knowing each one, I know which problem will excite someone, and I hear early when something is off. I used to fire fast, on the theory that a team trusts teammates who always deliver. Now I wait for the team to tell me someone is really a problem before I act, because some things take longer than a month to clear.
A cook came in late one night at the steakhouse, and I knew they would be wound up about it. I took them aside, said the work could wait, and we took a minute before service. That was cheaper than a cut hand or a burned plate.
Sit down, shut up, and leave silence
The best idea in the room can come from anyone, and it is often unsaid, waiting for a gap to interject or for a little more prodding. So I wait ten seconds after asking for questions, give people time to unmute, and don’t jump in when someone pauses to breathe.
When I lost my train of thought on a call, Raunak Singwi insisted I take a moment, and he meant it. The idea came back the second the pressure left. I have run meetings that way since.
Make the change something people want
I have watched teams reorged every quarter with no warning, eroding trust and morale. Smart people given objectives and room to operate get there themselves. So my changes have to be better for the people doing the work, and they see it coming.
At CyberGRX the new deploy process was pleasant to use, PRs spent less time in queue, and people got back to the interesting work. I announced it ahead of time, ran demos, and had people block the time. Fifty engineers were shipping with it inside 3 days.
“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
“Jake worked in the pit with [the operations team] and everyday came in with killer energy. Everyone else told us how to work around problems. Jake built us better tools.”
Magician, Magic
Sound like the role you’re hiring for?
Email me and let’s find out. My resume digs into the details if you need more convincing.
Or browse my projects & ventures. Screening with an AI assistant? Point it at ai.jakegaylor.com.