Member Of Technical Staff

SiftMed turns thousands of pages of messy medical records into a clear, source-linked account of what happened. Insurance claims teams, lawyers, life care planners, and independent medical experts use it to review a file in under 30 minutes instead of days. Behind every file is a person waiting on a decision about an accident or disability claim, and our job is to make sure that the facts that matter don’t get missed.

Founded in 2020 in St. John's, Newfoundland;
about $11 million raised, most recently a $5 million seed led by Staircase Ventures Revenue has more than doubled every six months Cuts medical record review time by 50-70%

The team: our small but mighty team of engineers all report directly to the CTO. We're based in St. John's, Newfoundland, with remote team members in Nova Scotia, New Brunswick, and Ontario. Four times a year, the whole company gets together outside the office for Boil-Up: a week of strategic planning and fun!

SiftMed is growing quickly, and our customers are asking for more: new use cases, bigger case files, and higher expectations for accuracy. We are looking for a senior engineer to help shape the platform for its next stage. It's a role with founding-engineer scope on a product that already has paying customers, and you'd work directly with the CTO on decisions that matter. Day to day, you'll move between UI, backend services, data pipelines, and cloud infrastructure.

Build reliable, event-driven pipelines that turn thousands of pages of medical records into structured, trustworthy output Keep the platform fault-tolerant and observable under real-world workloads as case volumes grow Work directly with customers to understand what they actually need, and turn competing requests into one product that works for insurers, lawyers, and life care planners alike

You balance pragmatism with technical excellence, and you know which one a problem calls for You're excited about AI tools and clear-eyed about their limits. You own what ships, no matter who or what wrote it You value visibility into the whole business: the numbers, the strategy, and the reasoning behind decisions You appreciate just enough process to ship well and no more You want your work to make a difference for real people, not just move a metric

Product ownership: Own features from the customer problem through to production and monitoring, working directly with the CTO, VP Product, and our customers

Technical direction: As one of our most senior engineers, shape how the platform grows, from the document pipeline to AWS infrastructure and security. Nothing is off-limits to rethink

Engineering practices: Help build the testing, release automation, and review habits that let a small team ship quickly and safely with AI coding tools

Mentorship: Help a team of 10 engineers grow through code review, pairing, and design feedback

• 5+ years building production web products across frontend and backend, including with React and Next.Js
• Built and run production systems in the cloud, including keeping them secure and reliable as usage grows
• Used AI coding tools every day, with the judgment to know when the output isn’t good enough
• Improved how a team builds software (code review, testing, and mentorship)
• Worked closely with customers or product to decide what to build, not just how to build it

• Have shipped features built on LLM APIs (prompting, evals, cost, latency)
• Have worked with sensitive data such as health, legal, or financial records
• Have built document-processing or data-heavy pipelines
• Have worked with AWS serverless and infrastructure-as-code (Lambda, Step Functions, Terraform or CloudFormation)
• Have helped a startup grow through its next stage

• Frontend: React and Next.Js in TypeScript
• Backend: NestJS REST API in TypeScript with Prisma;
  a public customer API that integrates with customers' systems
• Data: MySQL per customer, a central PostgreSQL platform database, OpenSearch for search, S3 for documents
• Pipelines: AWS Step Functions orchestrating Lambda and ECS tasks in TypeScript and Python for file preparation, classification, extraction, grouping and de-duplication
• AI: Several LLMs through AWS Bedrock, chosen per step, with fallbacks;
  prompts and model configuration managed as data, not code
• Infrastructure: AWS ECS Fargate, Cognito, Terraform, CloudWatch;
  separate processing accounts per region (Canada and US)
• CI and testing: Trunk-based development with tag-based releases cut by CI. Every PR gets its own production-like test environment, and Playwright and AI accuracy checks run there before review
• Dev tooling: Claude, Codex, and Cursor for every engineer, with a generous token budget. GitHub, Linear and PostHog, plus Skipper, our internal agent that turns requests into draft PRs and picks up routine chores overnight

Four interviews, usually within two to three weeks. There's no take-home.

Intro chat with our CTO (45 minutes). What the team is working on, what the role involves, and what you're looking for. We'll also cover compensation up front.

Technical session with our CTO and Chief AI Officer (90 minutes). We'll pick a real problem from our backlog and work on it together. Bring your own setup and whatever AI tools you normally use. Expect to read some unfamiliar code, decide what to build, write some of it, and talk through the tradeoffs. We care more about how you work than whether you finish.

Peer interview with an engineer and a product manager (45 minutes). How you work with others and how you think about what to build: handling conflicting requests, pushing back on a spec, getting a feature from a customer conversation to production. It's also your chance to ask the people you'd work with every day what it's actually like here.

Conversation with our CEO (45 minutes). Past experiences with ownership, ambiguity and disagreement, what you need from a company to do good work, and your questions about the business.

You'll hear from us within two business days after each interview, including if we decide not to move forward. Before an offer, we'll ask to speak with two or three references.

As a group, we never take ourselves too seriously but believe we truly can make a big difference. We work very hard but we also enjoy having fun. From pickleball, full company strategic offsites, and plenty of jokes in every meeting. We want everyone to be empowered, regardless of your role, you have a seat at the table and we want to hear from you.

We believe in trust and autonomy and therefore provide a flexible working environment. We want members of our team to be able to work closely together while also having the flexibility to manage their life and work responsibilities based on what works for each individual.

We're committed to building an inclusive, diverse, and equitable team, and we welcome applicants of all backgrounds. If you need an accommodation during the hiring process, let us know.