Product Manager (DevTools & AI Reliability, remote)

(Fully remote, async-first, DevTools SaaS, 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: 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. Now we need a PM who wants to take that further, in a market being rewritten in real time.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. Nobody has really figured out what reliability means for this kind of software yet. That's the problem you'd own.What you'll doAs a Product Manager, you will be responsible for empowering developers and designers to solve customer problems. You will work directly with our SVP Product Engineering Daniel.You will:Shape company and product strategy alongside our SVP of Product Engineering. It's a genuine partnership: you'll develop the vision for where Checkly goes next, decide where we play in the AI testing, monitoring, and observability landscape and where we don't, and turn that into a direction. You build the strategy with us, not execute someone else's.Shape Checkly's point of view on reliability in an AI-native world: how teams monitor AI-generated code, agent-driven workfl