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Checkly is a DevTools SaaS company that helps developers monitor and test software reliability through code-defined monitoring, powered by OpenTelemetry and Playwright. The company serves thousands of customers including AI-native companies like Mistral and large engineering organizations like LinkedIn, Citi, and 1Password.
As Product Manager for DevTools & AI Reliability, you will shape Checkly's product strategy and point of view on reliability in an AI-native world. You'll work directly with the SVP of Product Engineering as a genuine strategic partner—developing the vision for where Checkly plays in the AI testing, monitoring, and observability landscape, and translating that into actionable direction.
Key responsibilities include: leading cross-functional initiatives across Product Engineering, Sales, and Marketing; representing Checkly to customers and developer communities; developing Checkly's perspective on how teams monitor AI-generated code, agent-driven workflows, and LLM-backed features; and living deeply in the product and customer problems. You'll ship with AI where it creates value and know when not to use it.
You should be an ex-engineer, ex-founder, or ex-solutions engineer who has written and shipped real code. Startup experience is essential—you're comfortable with ambiguity, small teams, and owning outcomes end-to-end. Technical product experience, ideally in developer tools or adjacent domains, is expected. Experience in monitoring or observability is a nice-to-have. You're technical enough to prototype in code, pressure-test viability, and reason about APIs, MCLs, and system architecture without translation.
The role is fully remote within UTC-3 to UTC+3 time zones, async-first, 40 hours per week. The company is AI-forward (AI skepticism is not compatible with the culture), writes more than it talks, ships constantly with changing priorities, and prioritizes customer signals over internal hunches. You'll own both strategic and unglamorous work—there's no PM ops layer to delegate to.
Benefits include transparent salary, 27 days paid vacation plus local holidays, paid sick leave, up to 14 weeks paid parental leave, stock options, co-working or home office budget, and annual company kickoffs.
