Senior Product Engineer (DevTools & AI reliability, remote)

(Fully remote, async-first, DevTools SaaS, 32-40h/week, time zones: UTC-3 to UTC+3) The best developers don't wait for a customer to tell them something's broken. They catch it first, in the pull request, in staging, or in the checkout flow at 3am, before a single user notices. That instinct is Checkly's whole reason to exist. We give developers and their agents the tools to own reliability the way they own their code: end-to-end tests and synthetic monitoring defined as code, powered by OpenTelemetry and Playwright, versioned and reviewed like everything else they ship. From pull request to post-mortem, in one place. Thousands of them, from modern AI companies like Mistral and resolve.ai to large engineering orgs like LinkedIn, Citi, and 1Password, build with us. In 2024 we raised $20M in Series B funding from Balderton, CRV and Accel. Here's the thing about 2026: AI agents and coding assistants are shipping more software, faster, than any team could review by hand, and more of it is breaking in ways nobody has seen before. LLM-backed features fail probabilistically. Agents take actions no runbook anticipated. "Is my app healthy?" is becoming an unanswerable question for a whole generation of AI-native software. You will build reliability for this kind of software. Our stack is AI (Codex, Claude, use what you like best), Vue.js, TypeScript, Node.js, Golang, Postgres, ClickHouse and AWS. We ship to prod all day, every day. We practice Agile (not scrum) and take pride in good documentation and good looking products. We’re a remote-first startup that keeps things simple—low on meetings, high on productivity, and always shipping. If you love building cool things, working async, actually listening to and working with customers, and keeping it lean, you’ll fit right in! What you'll do 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. What you should have • 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 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 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. • You wo