{"id":3388486,"url":"https://alion.io/job/checkly-support-engineer-devtools-ai-reliability-remote","title":"Support Engineer (DevTools & AI Reliability, remote)","company":{"id":3061,"name":"Checkly","domain":"checklyhq.com","url":"https://alion.io/company/checkly","size_band":"51-200","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Ashby","truth_index":null},"role":"Support","role_family":"Support","seniority":null,"employment_type":"full_time","work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"board_field","remote_working_hours":null,"hiring_geo_confidence":"inferred","locations":["Boston, United States","Atlanta, United States","Tampa, United States","Philadelphia, United States"],"countries":["US"],"hiring_countries":["US"],"hiring_countries_total":1,"salary":{"min":43000,"max":87000,"currency":"USD","period":"year","gross":null,"usd_annual":87000},"salary_estimate":null,"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"AI Agents","optional":false},{"name":"CI/CD","optional":false},{"name":"Claude Code","optional":false},{"name":"Cursor","optional":false},{"name":"JavaScript","optional":false},{"name":"Node JS","optional":false},{"name":"OpenAI Codex","optional":false},{"name":"OpenTelemetry","optional":false},{"name":"Playwright","optional":false},{"name":"Rest API","optional":false},{"name":"TypeScript","optional":false}],"status":"live","first_seen_at":"2026-10-28T08:44:31Z","employer_posted_date":"2026-10-28","last_verified_at":"2026-10-30T21:23:54Z","board_verified":true,"closed_at":null,"days_open":2,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":2},"description":"(Remote, US East Coast or the same time zone. Series B. DevTools SaaS. Synthetic monitoring. 40h/week)\nThe best developers don’t wait for a customer to tell them something’s broken.\nThey 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. Now that agents write and ship more and more code, they can carry that instinct too. Agents write, run, and maintain the monitoring setup that guards production, while developers stay in control. Everything is defined as code, powered by OpenTelemetry and Playwright, and versioned and reviewed like everything else that ships. From pull request to post-mortem, in one place.\nAI agents are shipping more code than any team can review, and reliability is lagging behind. Checkly closes this gap. As a Support Engineer, you’ll support our most valuable customers, from modern AI companies like Mistral and resolve.ai to large engineering orgs like LinkedIn, Citi, and 1Password on that journey.\nIn 2024 we raised $20M in Series B funding from Balderton, CRV and Accel. We’re a remote-first startup that is low on meetings, high on productivity, and always shipping. If you love actually listening to and working with customers, working async, and keeping it lean, you’ll fit right in!\nWe care about building a team where people of all backgrounds are encouraged to do their best work. To achieve this we built a flexible and async-first startup environment with inclusive benefits and full transparency about how we pay.\nWhat you’ll do\nSupport has always been about solving real problems for real people. What’s changing at Checkly is how we do it: AI lets us automate routine work and assist us with troubleshooting, so we can go deeper on hard cases and bring what customers tell us straight back to the product. Here’s where you come in:\nResolve customer issues. Debug Playwright tests (flaky selectors, timeouts, auth flows). Dig into API check failures with packet captures (PCAPs), traceroutes and timing breakdowns. Set up single sign-on (SSO) and SAML. When it’s a bug, bring engineering a clean reproduction, or open the pull request (PR) yourself.\n\nBuild an outstanding AI support process. Our internal and external support agents already resolve 80% of tickets. You’ll help lift the bar: what the agent answers, when it hands off to a human, and how good those answers are.\n\nTurn tickets into product. Spot patterns across customers and bring product and engineering a reproduction. Your work becomes bug fixes and features.\n\nOwn the docs. If you’ve answered something twice, it belongs in the docs and in the agent, so customers and AI get the same right answer.\n\nWork with modern tooling. We are continuously updating our workbench, and you’ll have modern tools like Plain, Linear, and Mintlify.\n\nThis won't be the right role if you...\nWant a clear process for every situation before you act.\n\nWould rather code all day than talk to customers.\n\nSee AI tools as something you’ll get around to eventually.\n\nWant the structure and pace of a large company.\n\nWhat you should have\nYou will often speak with developers who need assistance understanding if their applications work well and if not, what caused the issue. This requires a solid technical background and a genuine motivation to help and learn.\nEmpathy: You love working with customers and solving their problems. Checkly is critical to them, and we genuinely want to unblock them.\n\nSome experience in a technical role, for example, as a developer or in technical support.\n\nYou can read and debug JavaScript, TypeScript and Node.js code.\n\nYou’re comfortable with HTTP, REST APIs, browser dev tools, git and CI/CD practices.\n\nAI is already how you work. Claude Code, Codex, Cursor or similar are part of your day. You’ve built your own workflows.\n\nYou write and speak clear, friendly English.\n\nYou can run your own day remotely and still enjoy working with your team.\n\nYou're based on the US East Coast or the same time zone.\n\nWhy us?\nTransparent salary because your salary shouldn't be dictated by how good a negotiator you are. (more info below)\n\nAsync-first (low meeting, high productivity) and transparent culture\n\nStock options\n\nFlexible paid vacation\n\nPaid sick leave & up to 14 weeks of paid parental leave\n\nUS: Medical, Dental, Vision, FSA, long- and short-term disability, life insurance, 401(k) and more\n\nAnnual company off-site\n\nFind out more here.\nWhat we pay\nFair, 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.\nFor this role, the range is\n$57,500 - $70,000 for someone in the US\n\n$71,910 - $87,000 for someone in US Tier 1 locations like NYC, Boston\n\n$43,000 - $52,000 for someone in e.g. South America\n\nApply\nIf 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!\nWe'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.","description_format":"text","description_chars":5558,"description_truncated":false,"requirements":{"experience_years_min":null,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[{"language":"English","level":"All levels","optional":false}]},"benefits":["Life insurance","Parental leave","Stock options"],"hiring_locations":[{"name":"United States","iso":"US","kind":"country"},{"name":"Philadelphia","iso":null,"kind":"city"},{"name":"Atlanta","iso":null,"kind":"city"},{"name":"Tampa","iso":null,"kind":"city"},{"name":"Boston","iso":null,"kind":"city"}],"hiring_excludes":[],"relocation_offered":false,"industries":["Software Testing & QA","Observability & APM"],"lifecycle":[{"event":"open","at":"2026-10-28T08:55:35Z"}],"visa":[],"liveness":{"score":86,"band":"hot","label":"Hiring now","p_open":1,"p_active":0.86,"p_room":1,"age_days":1,"expected_fill_days":35,"reasons":["conf:1","win:early"],"computed_at":"2026-10-30T05:48:23Z"},"pay":{"stated_usd_annual":87000,"is_top_pay":true},"html_url":"https://alion.io/job/checkly-support-engineer-devtools-ai-reliability-remote","json_url":"https://alion.io/job/checkly-support-engineer-devtools-ai-reliability-remote.json","meta":{"generated_at":"2026-10-30T22:26:47Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":13269,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-10-31T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":3061},"rest":"https://alion.io/mcp/rest/get_company?id=3061"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fcheckly-support-engineer-devtools-ai-reliability-remote"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fcheckly-support-engineer-devtools-ai-reliability-remote"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fcheckly-support-engineer-devtools-ai-reliability-remote"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/checkly-support-engineer-devtools-ai-reliability-remote\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fcheckly-support-engineer-devtools-ai-reliability-remote"}],"agent":{"mcp":"https://alion.io/mcp/jobs","mcp_open":"https://alion.io/mcp/open","next":[{"tool":"get_job","arguments":{"id":3388486}},{"tool":"search_jobs","arguments":{"company":"checklyhq.com","detail":"compact"}},{"tool":"match_people","arguments":{"job_id":3388486},"note":"people open to offers who fit this vacancy"}],"note":"The same data through MCP tools: https://alion.io/mcp/open needs no sign-in (compact searches, postings, people); https://alion.io/mcp with an Alion account has everything. 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