About Checkly
What is Checkly?
Checkly describes itself as a company that "was founded to enable developers to monitor their critical APIs and UIs easily", building "the best monitoring as code (MaC) platform for developers using modern stacks." Its postings say "Thousands" of developers use it, "from modern AI companies like Mistral and resolve.ai to large engineering orgs like LinkedIn, Citi, and 1Password", and that "In 2024 we raised $20M in Series B funding from Balderton, CRV and Accel." The product covers uptime and heartbeat monitoring, synthetic monitoring, Playwright checks, status pages and AI root cause analysis, with checks written in TypeScript in the customer's own repo.
Where will I work?
Checkly is remote-first: "Most of our team works remotely from 16+ countries, with flexible working hours. We've got a sales team in our NYC office". The open roles are remote, with location limits: the Senior Product Engineer role is "FULLY remote" within "the UTC-3 to UTC+3 time zones", with a requirement to travel to European countries for the annual kickoff, a team meetup or a conference, and the Solutions Engineer role is remote on the US East Coast. Company retreats have been held in Portugal (February 2026), Italy, Spain and Greece.
What is the Checkly team like?
The careers page lists values including "We Talk To Customers", "We ship results and follow up", "We assume good intentions" and "We are reliable and trustworthy". It is direct about fit: you won't be happy working there if you "need meetings to communicate and make decisions", and the postings say "We write more than we talk. We are async-first, so a lot of decisions happen in documents and threads, not meetings." It has open-sourced its employee handbook, publishes a hiring playbook and uses a standardized salary calculator.
Work-Life Balance
The postings describe a "Remote-first, flexible work hours, async-first and transparent culture" ("low meeting, high productivity"). The Senior Product Engineer posting is advertised as "32-40h/week", a stated range of working hours rather than a fixed week, and the Solutions Engineer posting carries no hours line. Time off is "27 days of paid vacation + your local public holidays" outside the US, and "flexible paid vacation" for US roles, with "Paid sick leave & up to 14 weeks of paid parental leave".
Perks and Benefits
- Remote-first, flexible work hours and an async-first culture
- 27 days of paid vacation plus local public holidays (non-US); flexible paid vacation (US)
- Paid sick leave and up to 14 weeks of paid parental leave
- Stock options and a transparent, calculator-based salary
- $1,500 learning, visiting and wellbeing budget
- Co-working budget or home office setup
- Annual company kickoffs and bi-annual company retreats