Product Manager (DevTools & AI Reliability) - Checkly

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.

What you'll do

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.

• Shape strategy: 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.
• AI reliability: 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.
• Cross-functional leadership: Lead initiatives across Product Engineering, Sales, and Marketing, representing Checkly directly to customers and developer communities.
• Hands-on immersion: Live in the product and the problem with deep empathy for DevOps, SRE, and Platform Engineering.
• AI-first execution: Ship with AI where it helps and know when not to.

What you should have

• Engineering background: Ex-engineer, ex-founder, or ex-solutions engineer who has written real code and can reason about APIs, MCPs, CLIs, and how systems fit together.
• Startup DNA: Comfortable with ambiguity, small teams, and owning outcomes end-to-end without a big-company machine.
• Technical product experience: Built technical products, ideally developer tools. Experience in monitoring or observability is a nice-to-have.
• AI fluency: Technical enough to be dangerous with AI tooling, able to prototype in code or throw together a mock.
• Location requirements: Fully remote role within the UTC-3 to UTC-3 time zones, with the ability to travel to European countries without visa wait times.

Benefits

• Transparent, standardized salary calculator based on market cost
• Remote-first, flexible work hours, and async-first culture
• Stock options
• 27 days of paid vacation plus local public holidays
• Paid sick leave & up to 14 weeks of paid parental leave
• Co-working budget or home office setup
• Annual company kickoffs