Product Manager (DevTools & AI Reliability, remote)

About the role

Checkly is looking for a Product Manager to lead its DevTools and AI reliability portfolio. You will shape the vision for monitoring AI‑generated code, agent‑driven workflows and LLM‑backed features, working fully remote with an async‑first culture.

Key responsibilities

• Shape company and product strategy together with the SVP of Product Engineering, defining where Checkly competes in AI testing, monitoring and observability.
• Develop Checkly’s point of view on reliability in an AI‑native world, influencing how teams monitor AI‑generated code and agent‑driven workflows.
• Lead cross‑functional initiatives across Product Engineering, Sales and Marketing, and represent Checkly to customers and developer communities.
• Live in the product and problem, empathising with DevOps, SRE and Platform Engineering teams.
• Ship AI‑enhanced features when they add value and know when to rely on traditional solutions.

Required profile

• Former engineer, founder or solutions engineer who has written and shipped real code.
• Experience in a startup environment, comfortable with ambiguity and end‑to‑end ownership.
• Background building technical products, ideally developer tools or adjacent solutions.
• Willingness to dive into AI tooling, prototype in code and validate technical viability.
• Open to a fully remote role within UTC‑3 to UTC+3 time zones and occasional travel in Europe.

Required skills

• APIs design and integration.
• Command‑line interface (CLI) development.
• Familiarity with OpenTelemetry.
• Experience with Playwright for testing.
• Hands‑on AI tooling and prototyping.

What we offer

• Transparent salary based on a standardized calculator (€83k‑€120k depending on seniority and location) plus stock options.
• Remote‑first, flexible hours and async‑first culture.
• 27 days paid vacation, public holidays, sick leave and up to 14 weeks paid parental leave.
• Co‑working budget or home‑office setup, annual company kick‑offs and stock options.