Chief Executive Officer

ROLE TITLE
Chief Executive Officer

COMPANY
My Well Self — Abby

LOCATION
Hamilton, Ontario (Remote-friendly)

EQUITY
20–30%

JOB TYPE
Co-founder

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ABOUT ABBY

Abby is an AI-powered health benefits assistant built to close the utilization gap between Canadian employees and their benefits plans.

Named one of Canada's Top 100 AI Start Up Companies in 2025, Abby uses large language models and conversational AI to help workers understand and act on their benefits — reducing waste for employers and improving health outcomes for employees.

We're in active commercial expansion, including a formal partnership with Quikcard, and are building toward a TotalRewards+ placement model.

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THE ROLE

We're looking for a proven operator to step in as CEO and own everything commercial.

You'll build and close our sales pipeline, lead BD and partnership strategy, and run day-to-day operations — while our visionary founder stays focused on KOL positioning and brand.

This is an equity-first role for someone who understands AI products deeply enough to sell and position them credibly — and who sees the white space in Canadian benefits technology.

Equity: 20–30% | Vesting: 4-year, 1-year cliff | Stage: Early / commercial

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A NOTE ON AI FLUENCY

You don't need to be an engineer — but you need to think like someone who understands what AI can and can't do. You should be comfortable discussing LLMs, conversational AI, and AI-powered product experiences with enterprise buyers, brokers, and partners. You'll be selling a product that lives at the intersection of AI and healthcare — and credibility in that conversation matters.

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WHAT YOU'LL OWN

• All revenue: sales pipeline, BD, partnership negotiations, and deal closure
• Commercial expansion with benefits brokers, TPAs, and small employer groups
• Management and growth of existing partner relationships (including Quikcard)
• Go-to-market strategy and execution, including AI product positioning
• Day-to-day operations: team, vendors, process, and execution rhythm
• Fundraising readiness and investor relationships when the time comes

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WHAT WE'RE LOOKING FOR

• Proven background in healthtech, benefits/HR tech, or B2B SaaS — ideally in a BD or sales leadership role
• Genuine working knowledge of AI: you understand how LLMs, conversational AI, and AI-powered products work at a functional level
• Able to speak credibly about AI capabilities, limitations, and value to non-technical buyers — brokers, HR leaders, and small business owners
• Experience selling to benefits brokers, TPAs, or small-to-mid-size employers
• Track record of closing partnerships and building commercial pipelines from early stages
• Comfortable operating as a generalist: you can sell, build process, and lead a small team
• A network in the Canadian benefits or employer health space is a strong asset
• Equity-motivated — you want ownership in something you're building, not just a salary

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WHAT THIS IS NOT

• A big-company role with a large team and budget — this is early-stage, scrappy, high-upside
• A purely technical or engineering role — you're leading commercial, not building the model
• A role where you're the public face of the brand — the founder retains that position

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A NOTE FROM THE FOUNDER

I built Abby to solve a real problem — people leaving benefits money on the table because the system is too complicated. I'm looking for someone who wants to take this commercial, understands AI well enough to represent it confidently, and has the relationships and drive to make it happen.

I'll stay close on vision.