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Full Stack Engineer (AI-Forward)

Posted 18 hours ago

Company Description

Chief Rebel helps business owners understand what their business is actually worth and what to do next.

Most founders don’t have clean numbers, clear options, or a real plan for an exit. They’re busy running the business, making decisions in the dark, and reacting instead of preparing. We exist to change that.

We work with owner-led businesses to bring clarity to valuation, readiness, and timing. Sometimes that means preparing for a sale. Sometimes it means fixing what would break a sale. Sometimes it means building a business worth keeping. We don’t push outcomes. We surface reality and help founders act on it.

We are not a brokerage or a coaching program.
We are a technology company focused on execution and precision.

Our work sits at the intersection of operations, finance, and real-world decision-making. The people who do well here are disciplined, direct, and comfortable talking to founders who don’t have time for fluff.

If you care about doing work that actually moves businesses forward and you take ownership seriously, you’ll fit in.

Why This Role Matters

The small business market is massive and almost entirely untouched by modern technology. We're building the platform that changes that. You won't be joining a team that's figured it all out. You'll be one of the people who figures it out, and your fingerprints will be on the architecture.


About the Role

You'll work directly with our Head of Engineering and Head of Operations, embedded in the core product team from day one. This is not a siloed role. You'll have visibility into how decisions get made and direct input into what gets built next.


What You'll Do

Own problems end to end. Discovery, design, build, deploy, and debug with minimal hand-holding.

On the technical side:

  • Build and extend a production-grade platform running Next.js, Go, Supabase, and an async job pipeline built for scale
  • Work across the full stack, React and TypeScript on the frontend, Go on the backend, with cloud infrastructure on Fly.io and Vercel
  • Integrate and manage AI workflows using large language models, document intelligence, and structured data extraction, and know when not to use AI at all
  • Build and improve async processing pipelines with signed delivery, auto-retry, and idempotency built in
  • Help design and build out our go-to-market funnel infrastructure, including tooling that supports outbound prospecting, lead enrichment, and off-market deal sourcing
  • Write clean, well-tested code and contribute to engineering standards as the team grows

On the team side:

  • Work closely with the Head of Engineering on architecture, code quality, and technical direction
  • Partner with the Head of Operations to build tooling that supports go-to-market execution and off-market deal sourcing
  • Translate vague requirements into working systems, and push back when the scope doesn't make sense
  • Help establish engineering culture and practices as the team grows

What We're Looking For

Skills matter. Mindset matters more.

We want someone who:

  • Has 5+ years of professional engineering experience, with real production systems to point to
  • Has built AI-integrated systems end to end, not just connected an interface, but thought through orchestration, output quality, and what happens when things go wrong
  • Is comfortable with Go or Python on the backend and React with TypeScript on the frontend
  • Has worked with PostgreSQL, async job queues, cloud infrastructure, and multi-tenant data design
  • Understands how to scope and ship under uncertainty without needing perfect requirements
  • Can talk through technical decisions with a non-technical founder and a developer in the same conversation
  • Has opinions about the current AI tooling landscape, including contrarian ones

Bonus if you have:

  • Experience building go-to-market or sales funnel tooling, outbound automation, or data enrichment pipelines
  • Familiarity with document parsing, financial data normalization, or working with messy real-world inputs
  • Background in tools built for small business, financial services, or professional services markets
  • Interest in how private companies are valued and what makes them attractive to buyers

What You Won't Find Here

A slow approval process. A 12-step standup ritual. A roadmap locked in six quarters ago.


What You Will Find

  • Direct access to leadership and real influence over product and technical direction
  • Flexible, remote-first work
  • Work with tangible impact on business owners who have spent years building something

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