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 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. What you should haveYou'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. What you will hate about usWe would rather tell you now than have you find out in month two. We use AI for everything, and we mean everything. AI skepticism is not a thing here. If you have the slightest hesitation about working with AI every day, this is not the place for you, and that is completely fine. We write more than we talk. We are async-first, so a lot of decisions happen in document