Senior Product Manager (AI / Document Intelligence)

Location: Toronto, Canada

Work model: On-site, 5 days per week

Salary: CAD $185K–$220K base + competitive equity + full benefits

Sponsorship: no visa sponsorship available

I'm hiring a Senior Product Manager for a Series B AI company building applied AI systems for high-stakes decisions in insurance. Their technology runs in production at some of the largest carriers in North America.

You'd own a brand-new AI-powered document intelligence product line as the first PM on the ground, reporting directly to the CEO.

The problem you'd help solve:

Insurance claims run on large volumes of messy, unstructured documents, and the decisions made from them are consequential — for the carrier and for the claimant. That puts hard constraints on the AI: fairness, auditability and low bias aren't features, they're requirements.

The company's core platform already does this at scale. The new product line extends it into document understanding — summaries, artifact generation, AI-assisted chat, and task management. It has early traction. It has no product manager.

You'd own that: the roadmap, the KPIs and success metrics defined from scratch, and the proof-of-concept engagements with enterprise insurance carriers that determine what gets built next. You'd work across engineering, design, sales, marketing, customer success and a new data team, and move between long-term strategy and hands-on execution depending on what the week needs.

This is 0-to-1 inside a company that already has distribution. You get the ambiguity of early product work without the risk of an unproven go-to-market.





You'll likely be a fit if you have:

- 5+ years in product management at growth-stage startups
- Shipped 0-to-1 products, not just optimised existing ones
- Owned enterprise B2B products with long sales cycles and demanding customers
- Run POCs directly with enterprise customers and turned that feedback into roadmap
- Defined success metrics and KPIs from nothing, and held yourself to them
- Genuine comfort with AI/ML and LLM-based products — enough to have credible technical conversations with engineers
- A strong data instinct: A/B testing, analytics, evidence over opinion

Nice to have:

- Insurance, insurtech, fintech, or another regulated, high-stakes domain
- Document processing, OCR, or document understanding products
- Experience as the first PM on a product line or in a company
- Background working closely with a founder or CEO

What you won't find here:

Flat structure, no bureaucracy, roughly 90 people. Direct communication is expected and hierarchy isn't a route to getting things done. It won't suit you if you want a defined lane, a layer of PMs to coordinate through, or product decisions made by consensus.

It's also genuinely 5 days a week in the Toronto office. The team eats lunch together daily and runs bi-annual offsites. If you want remote or hybrid flexibility, this isn't the role.

The package:

- CAD $185K–$220K base salary
- Competitive equity
- Full benefits — 100% premium coverage
- RRSP matching
- 4 weeks PTO
- In office, 5 days per week in Toronto
- No visa sponsorship — you'll need existing authorisation to work in Canada

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