Senior Product Engineer (DevTools & Artificial Intelligence Reliability)

• Build and ship with AI
• You will actively use coding agents for full stack development, from exploring solutions and generating scaffolding to refactoring, test generation and debugging. At Checkly we push the limits of AI tools every day
• Talk to our users
• You will talk directly to the developers, DevOps and Site Reliability Engineering (SRE) teams who are on-call, debugging incidents, or wiring Checkly into production pipelines. You will understand their workflows, pain points, and feedback. You use those conversations to validate ideas, course-correct early, and iterate on what you build. Customer calls and the weekly support rotation are part of the job, not a distraction from it
• Find the right problems to solve
• In a world where the cost of building software trends to zero, the hard part is picking what to build. You will focus on real developer pain: flaky tests and flaky checks, unclear failures, noisy alerts. You will favour pragmatic solutions that ship quickly, validate assumptions in production, and compound into long-term reliability improvements
• Own your work end to end
• From shaping the initial idea, through implementation and rollout, to watching how it behaves in production. You will take part in on-call and help support customers when things don’t work as expected
• We would rather tell you now than have you find out in month two
• We use AI for everything, and we mean everything. AI skepticism is not a thing here. If you have the slightest hesitation about working with AI every day, this is not the place for you, and that is completely fine
• We write more than we talk. We are async-first, so a lot of decisions happen in documents and threads, not meetings. If you do your best thinking out loud in a room full of people, you will miss it here
• We are lean, so you own the unglamorous parts too. There is no separate QA team, no ops layer to hand things off to, and you are on the support rotation and the on-call rotation like everyone else
• We ship constantly and change our minds. Priorities move as we learn from customers. If you need long, stable planning cycles, this will feel chaotic
• Customer signals come first, and most of the time they matter more than your instinct. We build what customers actually want, not the clever thing we dreamed up

Benefits

• Competitive salary & stock options
• 27 days of vacation & local public holidays
• Inclusive health package
• Home office setup
• Team retreats
• Inclusive paid parental leave
• Employment & contractor options
• Paid sick leave
• $1,500 learning, visiting & wellbeing budget
• Remote-first- Studies by several different sources have shown that on average men will apply for a job if they meet 60% of the application requirements. Women, non-binary people and POC will seek to match a much higher percentage of requirements before applying. If you’re not sure you’re the right fit, apply anyway and let us know what you bring to the table. We’d love to hear from you!
• You have built and run production software. You know the realities of operating software that people depend on: edge cases, incidents, regressions, and the need for observability and follow-up. You are not surprised when things break. You help fix them
• You work well without an office around you. You are autonomous and self-motivated in a remote setup, and you still enjoy getting to know your colleagues and helping other people get unstuck
• You have shipped features with AI, not just experimented with them. You have taken work from zero to shipped with a comparable stack, made implementation decisions that held up, and put things in front of real users
• You can hold a product conversation, not just a technical one. You can look at a customer problem and reason about whether the thing we are about to build actually solves it
• FULLY remote role, within the UTC-3 to UTC+3 time zones. You need to be able to travel to (other) European countries without having to wait for a visa appointment, for our annual kickoff, a team meetup or a conference