Senior Product Engineer (DevTools & AI reliability, remote) - #2686673

(Fully remote, async-first, DevTools SaaS, 32-40h/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: end-to-end tests and synthetic 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. In 2024 we raised $20M in Series B funding from Balderton, CRV and Accel.

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. You will build reliability for this kind of software.

Our stack is AI (Codex, Claude, use what you like best), Vue.js, TypeScript, Node.js, Golang, Postgres, ClickHouse and AWS. We ship to prod all day, every day. We practice Agile (not scrum) and take pride in good documentation and good looking products.

We’re a remote-first startup that keeps things simple—low on meetings, high on productivity, and always shipping. If you love building cool things, working async, actually listening to and working with customers, and keeping it lean, you’ll fit right in!

What You'll Do

Build and ship with AI

You will actively use coding agents for full stack development, from exploring solutions and generating scaffolding to refactoring, test generation and debugging. At Checkly we push the limits of AI tools every day.

Talk to our users

You will talk directly to the developers, DevOps and Site Reliability Engineering (SRE) teams who are on-call, debugging incidents, or wiring Checkly into production pipelines. You will understand their workflows, pain points, and feedback. You use those conversations to validate ideas, course-correct early, and iterate on what you build. Customer calls and the weekly support rotation are part of the job, not a distraction from it.

Find the right problems to solve

In a world where the cost of building software trends to zero, the hard part is picking what to build. You will focus on real developer pain: flaky tests and flaky checks, unclear failures, noisy alerts. You will favour pragmatic solutions that ship quickly, validate assumptions in production, and compound into long-term reliability improvements.

Own your work end to end

From shaping the initial idea, through implementation and rollout, to watching how it behaves in production. You will take part in on-call and help support customers when things don’t work as expected.

What You Should Have

• You have shipped features with AI, not just experimented with them. You have taken work from zero to shipped with a comparable stack, made implementation decisions that held up, and put things in front of real users.
• You have built and run production software. You know the realities of operating software that people depend on: edge cases, incidents, regressions, and the need for observability and follow-up. You are not surprised when things break. You help fix them.
• You can hold a product conversation, not just a technical one. You can look at a customer problem and reason about whether the thing we are about to build actually solves it.
• You work well without an office around you. You are autonomous and self-motivated in a remote setup, and you still enjoy getting to know your colleagues and helping other people get unstuck.
• FULLY remote role, within the UTC-3 to UTC+3 time zones. You need to be able to travel to (other) European countries without having to wait for a visa appointment, for our annual kickoff, a team meetup or a conference.
  
  

What You Will Hate About Us

We 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 documents and threads, not meetings. If you do your best thinking out loud in a room full of people, you will miss it here.
• We are lean, so you own the unglamorous parts too. There is no separate QA team, no ops layer to hand things off to, and you are on the support rotation and the on-call rotation like everyone else.
• We ship constantly and change our minds. Priorities move as we learn from customers. If you need long, stable planning cycles, this will feel chaotic.
• Customer signals come first, and most of the time they matter more than your instinct. We build what customers actually want, not the clever thing we dreamed up.
  
  

Benefits

• 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
  
  

Find out more here.

What We Pay

Fair, competitive, and transparent pay is very important for us. Therefore we work with a standardized salary calculator that includes several factors such as seniority level as well as location.

For this role, the range is

• €88k - €105k for someone in a similar cost of market as UK, Germany etc, + stock options
• €79k - €97k for someone in a similar cost of market as Spain, Poland, Ukraine etc, + stock options
  
  

Apply

If this sounds interesting, please apply! Studies by several different sources have shown that on average men will apply for a job if they meet 60% of the application requirements. Women, non-binary people and POC will seek to match a much higher percentage of requirements before applying. If you're not sure you're the right fit, apply anyway and let us know what you bring to the table. We'd love to hear from you!

We're all about being transparent and setting clear expectations. That's why we've put together our hiring playbook and open-sourced our employee handbook. There you'll find a sneak peek of who we are, how we work and what you can expect in our hiring process.

Compensation Range: €79K - €105K