This story was written in collaboration with Sawyer Celentano, part of the team bringing Middesk’s stories to life.
When Clay Tondreau joined Middesk more than three years ago, he was an engineer drawn to the company’s mission and its technical challenges. Since then, he’s helped shape the systems that power Middesk’s growth, from early internal tools to the infrastructure behind the company’s next generation of products.
Now, as a Software Engineering Manager, Clay leads a growing team that’s tackling complex problems with speed, curiosity, and collaboration. His path at Middesk reflects what makes the company’s engineering culture special: a place where hands-on builders can grow into leaders while continuing to stay close to the code.
In this conversation, Clay shares how his role — and the engineering team — have evolved, what makes building at Middesk different, and why he’s excited for what’s ahead.
What keeps you inspired at Middesk?
“The product, the people, and the pace.
On the product side, I believe in the vision. We’re building tools that make life easier for businesses — from mom-and-pop shops trying to run payroll to large organizations managing compliance. That impact is inspiring.
The people are just as important. We consistently hire folks who are passionate and bring their whole selves to work. Being surrounded by that energy pushes you to deliver your best.
And then there’s the pace. We move quickly, iterate constantly, and it keeps things exciting. You never feel like you’re doing the same thing day after day — there’s always a new problem to crack.”
What’s been one of your proudest moments at Middesk so far?
“Besides growing into leadership, one moment that stands out is when we took a hackathon idea and, in under a month, shipped a brand-new internal fulfillment system.
It broke complex government workflows into easy-to-use tasks, paired with a dynamic template system our Ops team could configure themselves. Suddenly, online forms could be autofilled in a way that fundamentally changed how onboarding and scaling worked.
For the team that used it, there’s a real line in the sand: before this system, and after. It was incredible to see how quickly an idea turned into something that transformed the business.”
What makes engineering at Middesk different from other organizations?
“Engineers here aren’t just closing tickets. They’re expected to think like product owners.
That means seeing work through end to end — from the earliest product discussions and business logic all the way to delivery. Our engineers influence design, weigh in on tradeoffs, and work directly with Ops, GTM, and Partners to understand the ‘why’ behind what we’re building.
It’s not about checking the box. It’s about solving complex zero-to-one problems, scaling them responsibly, and making sure what we ship actually makes a difference for customers. That ownership makes the work harder, but also much more rewarding.”
What technical challenges excite you right now?
“We’re in a fun spot: we’re solving zero-to-one problems while also figuring out how to scale what we’ve already built.
On one side, we’re building cross-functional systems that handle business and operational logic. On the other, we’re pushing for faster, smarter solutions — whether that’s upgrading our frontend, improving infrastructure, or exploring AI-native technologies.
And we don’t just chase AI for AI’s sake. We test hypotheses quickly, look for repeatability, keep humans in the loop when needed, and double down when something actually works. It keeps us sharp, and it keeps us honest.”
Tell us about your team — who they are and how do they work together?
“We’ve grown quickly, from 2 engineers to 7 in just six months, so there’s a lot of energy. The team is a mix of backgrounds, interests, and career goals, but everyone shares the same collaborative, product-minded approach.
One ritual I’m proud of is how we capture knowledge. As new people join, we run deep-dive sessions on different parts of the system, record them, and save them as a growing library. That way, we’re not just documenting what the code does, but also why we made certain decisions. It helps new hires ramp faster, and it preserves the thinking behind tradeoffs we made while moving fast.
That kind of shared context is essential when you’re scaling a team — it ensures we can all keep learning and leveling up together.”
Of Middesk’s values — lead with curiosity, embrace ambition, win together, put customers first — which do you find yourself living out the most?
“Win together.
A great product doesn’t succeed in isolation. It takes a well-designed product, strong go-to-market, and seamless operations. Engineering has to work shoulder to shoulder with every function.
We also make sure engineers are in the room early, helping shape the ‘why.’ That way, by the time we ship, it feels like a collective win. That team mindset is what drives results and keeps people growing.”
What would you tell an engineer thinking about joining Middesk?
“Bring curiosity, ambition, and ownership.
You’ll have the chance to propose ideas, try new approaches, and see them go from concept to impact. We move fast, we support one another, and we’re building products that make a real difference for businesses.
We’re also a Rails and React/TypeScript shop, but we’re stack-agnostic when it comes to hiring. What matters most is curiosity and problem-solving — not the language. The problems are complex, and they require both autonomy and collaboration to solve well.
If that excites you — and you want to grow with a team that wins together — Middesk is the place.”
Did you know?
Clay’s engineering team is growing. Want in? Visit our careers page and apply!
