Principal Engineer & Technology Lead

We’re an insurance services firm processing hundreds of thousands of audits a year for our clients on a C#/.NET application hosted on AWS. We need a builder who can open the debugger, read the production code, and make the current system faster, safer, and more reliable - while also owning the infrastructure it runs on and the people who depend on it.

This is a hands-on principal-engineer role with technology leadership scope. You’ll spend most of your time in code and infrastructure, not in meetings. Once the current system is stable and you’ve built trust with the team and executive group, you’ll with the team on the build-out of our next-generation, AI-augmented audit platform - but that’s Phase 2, not Day 1. If you’re a senior IC who wants real scope and ownership without giving up your keyboard, keep reading.

What You’ll Own

Phase 1 - Stabilize and modernize the current system (first ~6-12 months)

• Own the C#/.NET application end-to-end. Read the code, fix the bugs, tighten the tests, cut down the incident rate. You should be committing meaningful code in your first two weeks.
• Take ownership of the AWS environment the platform runs on. Right-size cost, tighten security, close observability gaps, harden the deploy pipeline.
• Establish the operational fundamentals we don’t have today: CI/CD that deploys safely, monitoring that catches regressions before customers do, runbooks a new engineer can actually follow, on-call that isn’t ‘call the founder.’
• Code review, architecture guidance, and doing the unglamorous plumbing that lets them ship.
• Support ~135 auditors on the day-to-day: identity (SSO, MFA), laptops, collaboration tooling, onboarding, incident response. You’ll hire a help-desk person early to offload the ticket queue, but you own the outcomes until they’re in seat.
• Own security and compliance. Manage vendor risk, lead the response when something breaks.

Phase 2 - AI-augmented audit platform (after Phase 1)

• Help design and lead the build of our next-generation platform: LLM-augmented audit workflows, automated client-deliverable generation, smarter billing operations.
• Own the AI stack - OpenAI or Azure AI services, orchestration, vector databases, evals, cost controls, guardrails.
• Make thoughtful build-vs-buy calls in a fast-moving space. Bring practical recommendations to leadership, not vendor pitches., You’ll inherit a real business - hundreds of thousands of audits processed annually, ~135 auditors depending on the platform - with executive support, real budget, and the mandate to fix things properly instead of patching them. If you’re a senior engineer who has wanted the scope and authority to design a system the right way, without giving up hands-on work, this role gives you both.

• 10+ years writing production software, with a substantial recent stretch in C#/.NET. You should be productive in Visual Studio or Rider on our codebase within the first week.
• Deep, hands-on AWS. You’ve architected, deployed, and operated real systems there - not overseen it from a program-manager seat.
• Strong track record running production systems: uptime, cost, security, observability. You’ve been paged, and you’ve fixed the thing.
• Comfortable being both the most technical person in the room and the person who unclogs the drain.
• A recent, credible track record of shipping. If we look at your last three years, we should see systems in production that you personally built or led - not decks and roadmaps.
• Excellent judgment on what to fix now, what to fix later, and what to leave alone. You’ve inherited legacy code before and you didn’t rewrite it on day one.
• Comfort in a small-firm environment. You’ll make decisions with incomplete information, wear several hats, and have no one to escalate to.

Nice-to-haves

• Azure alongside AWS - we may use both as the AI stack takes shape.
• Practical experience shipping systems that use OpenAI or another LLM API in production (not proofs-of-concept).
• Insurance, financial services, audit, or another regulated-industry background.

Pulled from the full job description 401(k) Health insurance 401(k) matching Vision insurance Health savings account Dental insurance Flexible schedule, * 401(k) with matching

• Health, dental, and vision insurance
• Flexible schedule

Pay: $80,000.00 - $130,000.00 per year, * 401(k)

• 401(k) matching
• Dental insurance
• Flexible schedule
• Health insurance
• Health savings account
• Vision insurance