Caledon
We're Hiring

Build the future of
financial AI

We're creating the data infrastructure that makes AI reliable for finance. Join a small team solving hard problems with real customers.

View open rolesToronto, Canada

Why This Matters

Financial AI is one of the hardest problems in the industry. LLMs hallucinate. They make confident mistakes. In finance, that's not acceptable. Every number matters. Every calculation needs to be auditable.

Most companies trying to apply AI to finance hit the same wall: the data isn't good enough. Models trained on generic data don't understand GAAP, tax codes, or the nuances of financial reporting.

We work with vetted CPAs, CFOs, and financial analysts to create expert-validated datasets. Our tools enable rigorous annotation, validation, and quality control at scale.

This is early-stage work with real customers and real traction. You'll have direct impact on a problem that matters.

What You Get

Proven traction

We're already profitable. This isn't a bet on an idea—it's a bet on scaling something that works.

Accelerated growth

You'll work across the full stack. The decisions you make here in one year would take five anywhere else.

Zero layers

No politics. Sit next to the people making decisions and have a real voice in where we go.

Profit sharing

As we grow, you participate directly in the profits. We want builders to get wealthy from their work.

Founder-caliber team

The people here could start their own companies. They chose to build this instead. You'll work alongside people who push you to be better.

What We Expect

Speed is the default

We ship features in days, not weeks. If you're used to quarterly roadmaps, this will feel different.

High intensity

We move fast and expect a lot. This isn't a 9-to-5. We're building something ambitious.

High autonomy

You'll own outcomes, not tasks. Figure it out, ask for help when you need it, and deliver.

Comfort with ambiguity

Priorities shift. Projects get scrapped. If you need everything defined before acting, this isn't for you.

Hiring Philosophy

"We hire for slope, not y-intercept."

If you learn fast and get things done, we care more about that than your resume. If you don't meet every requirement but believe you'd be a good fit, reach out anyway.

Open Positions

Current opportunities to join the team.

Head of Delivery

Full-timeToronto3+ years

Own the success of our most important client relationships. You'll be the strategic bridge between enterprise financial teams and our engineering org—translating complex requirements into shipped solutions and ensuring every deployment drives measurable value.

What you'll do

  • Lead end-to-end delivery for enterprise clients, from kickoff to production
  • Translate CPA and CFO requirements into clear technical specifications
  • Build and refine our delivery playbook as we scale
  • Identify expansion opportunities and drive product adoption
  • Coordinate cross-functional teams to hit aggressive timelines

What we're looking for

  • 3+ years in technical delivery, solutions engineering, or client success
  • Experience in B2B SaaS—fintech or data infrastructure preferred
  • Technical fluency: comfortable reading API docs and writing basic SQL
  • Strong written and verbal communication skills
  • Bias toward action and comfort with ambiguity
Apply Now

Senior Software Engineer

Full-timeToronto5+ years

Build the core infrastructure that makes financial AI reliable. You'll work across the full stack—from data pipelines that process millions of financial documents to the interfaces that financial experts use to validate AI outputs. This is greenfield work where your architectural decisions will define the product.

What you'll do

  • Design and build scalable pipelines for processing unstructured financial data
  • Develop Python backend services with strict accuracy and auditability requirements
  • Create intuitive React interfaces for expert data annotation and validation
  • Own reliability, observability, and performance for mission-critical systems
  • Shape technical direction and mentor junior engineers as we grow

What we're looking for

  • 5+ years building production software systems
  • Deep proficiency in Python (FastAPI, async patterns, type hints)
  • Strong TypeScript and React experience
  • Experience with SQL optimization and data modeling
  • Familiarity with AWS or similar cloud infrastructure

Tech stack

PythonTypeScriptReactNext.jsPostgreSQLAWS
Apply Now

Don't see a role that fits?

We're always looking for exceptional people. Reach out and tell us about yourself.

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