Product Manager (DevTools & AI Reliability, remote)

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.

• 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 workflows, and LLM-backed features
• Lead initiatives across Product Engineering, Sales and Marketing, and represent Checkly directly to customers and in developer communities.
• Live in the product and the problem. Empathy for DevOps, SRE and Platform Engineering isn't a line item. It's the job.
• You ship with AI where it helps and know when not to. You don't just talk about it.

• You've built software before this. You're an ex-engineer, ex-founder, or ex-solutions engineer who has written real code and shipped real things, and now you want to own the product. This one's non-negotiable: you should be able to reason about APIs, MCPs, CLIs, and how systems fit together without a translator.
• You've worked in a startup, not just a big company. You're comfortable with ambiguity, small teams, and owning outcomes end to end. You don't need a big-company machine around you to be effective.
• You've built technical products, ideally developer tools. Adjacent technical products count. Experience in monitoring or observability is a nice-to-have, not a requirement.
• New to the PM title? That's fine. If you're coming from a founding or solutions-engineering seat and want to go all-in on product, we want to hear from you.
• You're technical enough to be dangerous with AI tooling. You can prototype in code, throw together a mock, or pressure-test technical viability yourself when it moves things forward.
• FULLY remote role, within the UTC-3 to UTC+3 time zones. Need to be able to travel to (other) European countries without having to wait for a visa appointment.

• Transparent salary because your salary shouldn't be dictated by how good a negotiator you are. (more info below)
• Remote-first, flexible work hours, async-first (low meeting, high productivity) and transparent culture
• Become part of a fast-growing, international, and remote team where your work matters, and your impact won't get lost in layers of bureaucracy.
• Stock options
• 27 days of paid vacation + your local public holidays
• Paid sick leave & up to 14 weeks of paid parental leave
• Co-working budget or home office setup
• Annual company kickoffs
• Employee & contractor options