Lead Technical Support Engineer

About HappyRobot

HappyRobot is the infrastructure for enterprises to build and orchestrate AI workforces. Our AI workers don't just communicate - they make decisions, take action, and run operations autonomously across voice, email, and enterprise systems. Born in Y Combinator (S23) and backed by a16z and Base10 with over $60M raised, we power critical operations for global enterprises worldwide.

Our platform is battle-tested in the most demanding environments - where AI has real consequences. We started in logistics, built our own voice stack, models, and orchestration layer from the ground up, and are now bringing that infrastructure to every enterprise that runs the real economy. Learn more about our vision in our manifesto.

About the Role

We’re looking for a Lead Technical Support Engineer to be the bridge between our customers and our tech. You’ll be the first person users turn to when something breaks—or when they’re just a little confused. You’ll work closely with engineering, product, and ops to fix bugs, improve workflows, and make our AI workers smarter and more reliable.

This is a high-trust, high-impact role. You’ll own customer-facing troubleshooting, root cause investigations, and escalations. You’ll turn noise into signal, helping the whole company learn faster from user pain.

If you love solving puzzles, calming chaos, and making things just work, this one’s for you.

Must-Have

• 3+ years of experience in a technical support, solutions engineering, or SRE-like role

• Comfort working with APIs, logs, databases, and modern web stacks (we use Python, JSON, Postgres, etc.)

• Clear, calm written communication — especially when customers are stuck or frustrated

• Curiosity and grit — you’ll go deep to figure out what’s actually going wrong

• High ownership mentality — if something is broken, you fix it or escalate it fast

• Comfort juggling a mix of tickets, tools, and ad hoc problem-solving every day

Nice-to-Have

• Experience with support platforms like Intercom, Linear, or Zendesk

• Ability to write scripts or tooling (in Python, Bash, or similar) to automate repetitive workflows

• Exposure to observability tools like Sentry, Datadog, or Grafana

• Experience supporting AI/ML, data-intensive systems, or developer-facing tools

• Previous work in logistics, operations tech, or comms-heavy B2B platforms

Why Join Us?

• Rapidly growing and backed by top investors including a16z, Y Combinator, and Base10.

• Top-Tier Compensation — Competitive salary + equity in a rocketship

• Ownership & Autonomy — You’ll own critical systems and shape user experience

• Real Impact — Every customer you help keeps freight moving and businesses running

• Work With the Best — Join a world-class team of builders, engineers, and operators

Our Operating Principles

Extreme Ownership

We take full responsibility for our work, outcomes, and team success. No excuses, no blame-shifting — if something needs fixing, we own it and make it better. This means stepping up, even when it’s not “your job.” If a ball is dropped, we pick it up. If a customer is unhappy, we fix it. If a process is broken, we redesign it. We don’t wait for someone else to solve it — we lead with accountability and expect the same from those around us.

Craftsmanship

Putting care and intention into every task, striving for excellence, and taking deep ownership of the quality and outcome of your work. Craftsmanship means never settling for “just fine.” We sweat the details because details compound. Whether it’s a product feature, an internal doc, or a sales call — we treat it as a reflection of our standards. We aim to deliver jaw-dropping customer experiences by being curious, meticulous, and proud of what we build — even when nobody’s watching.

We are “majos”
Be friendly & have fun with your coworkers. Always be genuine & honest, but kind. “Majo” is our way of saying: be a good human. Be approachable, helpful, and warm. We’re building something ambitious, and it’s easier (and more fun) when we enjoy the ride together. We give feedback with kindness, challenge each other with respect, and celebrate wins together without ego.

Urgency with Focus
Create the highest impact in the shortest amount of time. Move fast, but in the right direction. We operate with speed because time is our most limited resource. But speed without focus is chaos. We prioritize ruthlessly, act decisively, and stay aligned. We aim for high leverage: the biggest results from the simplest, smartest actions. We’re running a high-speed marathon — not a sprint with no strategy.

Talent Density and Meritocracy
Hire only people who can raise the average; ‘exceptional performance is the passing grade.’ Ability trumps seniority. We believe the best teams are built on talent density — every hire should raise the bar. We reward contribution, not titles or tenure. We give ownership to those who earn it, and we all hold each other to a high standard. A-players want to work with other A-players — that’s how we win.

First-Principles Thinking
Strip a problem to physics-level facts, ignore industry dogma, rebuild the solution from scratch. We don’t copy-paste solutions. We go back to basics, ask why things are the way they are, and rebuild from the ground up if needed. This mindset pushes us to innovate, challenge stale assumptions, and move faster than incumbents. It’s how we build what others think is impossible.