Steve Regester
Engineering manager
Fifteen years building software
Led small teams at an AI security startup and a pharma-research platform
Southwest Washington • Portland Metro Area • Open to engineering manager roles, remote or local
The short version
I'm an engineering manager. For fifteen years I've built software in domains where the details matter — mobile security at Lookout, crowdsourced pentesting at Synack, pharma research at Studylog, AI binary analysis at Delphos — and since 2021 I've led the small teams that build it.
At Studylog Systems and at Delphos Labs I managed a team of three: hiring, performance reviews, and roadmap and stakeholder negotiation. I hire for talent over experience, I cut every ask down to its minimum valuable version, and I coach engineers toward the point where they no longer need me in their pull requests.
Most recently I was a founding engineer at DesignForge AI, which shut down in October 2026, and I'm making the move back into engineering leadership.
What I'm good at
I started writing code because it was the closest thing I'd found to magic — the ability to make an idea real. Fifteen years later, that's still the part I care about. I've spent that time in domains where the details matter: mobile security at Lookout, crowdsourced pentesting at Synack, pharma research at Studylog, AI binary analysis at Delphos.
The thing I keep coming back to is the feel of software — the difference between systems that flow and systems that grind. Good software respects momentum and the person on the other side of the screen. What I want now is to lead the team that builds it.
How I lead
How I hire
I look for talent over experience. It shows up as enthusiasm, the stories people tell about things they've built, and what they do on their own time. My interview is one simple problem that gets harder as we go and has more than one good answer. I keep it conversational and relaxed, because what I want to know is what it would feel like to work next to this person every day.
How I grow people
The measure I remember best: an engineer whose pull requests I used to leave a lot of comments on, and after a while I stopped needing to. The standard had moved into their head, which was the whole point.
Hard conversations
I try to see the other side before I deliver anything difficult, and I try to deliver it with kindness. Nothing should be a surprise, so I raise concerns early and in small doses. Sometimes the news is genuinely bad, and I feel awful delivering it. There's still a chance to listen and to learn something.
Roadmaps and stakeholders
When someone wants too much for a first release, I cut it down to its minimum valuable version, ship that well, and build on it. Yes, no, wait. The core ask is a yes. The bells and whistles are usually a wait, and some of the extras are a no.
Once a product designer wanted a long list of features in the first release. I offered the core set up front and a sequenced plan for the rest. She wasn't pleased, but most of it shipped over the following weeks.
When someone is stuck
Most engineers will tell you. When they do, I sit down and act as a sounding board without solving it for them, and I bring in a teammate with the right experience if that isn't enough. The ones to watch are the engineers who power through a stuck ticket quietly. You can see it in standup if you're paying attention.
What good looks like now
I prefer small pull requests scoped to a single bounded piece of work. Beyond that, I'll be honest: the pull request was historically where the craftsmanship filter lived, and it doesn't feel like many people are writing or reading code that way anymore. I don't know where that standard lives now. I'm paying attention.
What colleagues say
"He goes above and beyond to break down complex concepts… while allowing you the autonomy to learn from your failures, creating a culture of intellectual vulnerability. Steve doesn't settle for mediocre code; he consistently delivers beautiful, clear, best-practice code."
— Christina Wright, who reported to Steve at Studylog
"Steve architected and developed a cloud-native platform… passing a rigorous third-party security audit and achieving the company's first SOC 2. He also recruited and mentored a talented team."
— Brad Nemer, who managed Steve at Studylog
"Steve's patience, clarity and thoughtfulness are exactly the qualities you'd look for in a staff full-stack engineer if not a CTO. Steve is a joy to work with."
— Faye Salwin, Platform Engineer at Delphos Labs
"Steve still represents the high-water mark for me in terms of sheer front-end engineering talent… equally passionate about doing things the right way, at a high level of quality."
— Derek Halliday, Chief Product Officer at Benchling
"His ability to get a good overview of large and complex systems and design and implement elegant solutions for them is very impressive. He always pushed for the right solution first."
— Christophe Verbinnen, Principal Architect at KnowBe4
"I haven't before or since met anyone more passionate about engineering front-end applications in a structured way. His skills were in very high demand and allowed us to build web-based tools for very complex analysis workflows."
— Mikko Tervahauta, Staff Engineer at Oura (led Steve at Lookout)
More references available on LinkedIn.
Let's talk
I'm looking for engineering manager roles at startups and growth-stage companies with product engineering teams: a small team, real users, and problems worth the care. If that's you, let's talk.
Open to engineering manager roles • Remote or Portland metro