Product Manager (DevTools & AI Reliability, remote)

About Checkly

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 teams — 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.

About the Role

As 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.

What You’ll Do

• Shape company and product strategy alongside the SVP of Product Engineering. Develop the vision for where Checkly goes next, decide where we play in the AI testing, monitoring, and observability landscape, and turn that into direction.

• 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; represent Checkly directly to customers and developer communities.

• Live in the product and the problem — empathy for DevOps, SRE, and Platform Engineering is the job.

• Ship with AI where it helps, and know when not to.

What You Should Have

• Background in building software — ex-engineer, ex-founder, or ex-solutions engineer who has written real code and shipped real things.

• Startup experience: comfortable with ambiguity, small teams, and owning outcomes end to end.

• Experience building technical products, ideally developer tools (monitoring/observability is a nice-to-have).

• Technical enough to prototype in code, mock ideas, or pressure-test viability yourself.

• New to the PM title? That’s fine — founding or solutions-engineering backgrounds welcome.

Location: Fully remote role, within UTC-3 to UTC+3 time zones. Must be able to travel to European countries without visa delays.

What You Will Hate About Us

• We use AI for everything. AI skepticism is not a fit here.

• Async-first culture: decisions happen in documents and threads, not meetings.

• Lean team: you own the boring parts too.

• Constant shipping and changing priorities — if you need long, stable cycles, this will feel chaotic.

• Customer signals come first — moonshots only after proven customer value.

Benefits

• Transparent salary — no negotiation games.

• Remote-first, flexible hours, async-first culture.

• Stock options.

• 27 days of paid vacation + 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-first environment.