Chief Marketing Officer; CMO

Position: Chief Marketing Officer (CMO)
CMO/Head of Marketing
King Street East, Toronto, Ontario, Canada, M5A 1L3 full-time . October 11, 2026

About Chexy
At Chexy, we're building modern financial tools for Canadians, starting with their largest expenses. We turned rent, mortgages, tuition, insurance and other big bills into opportunities to earn rewards, improve cash flow and get more from money they already have to spend.

We're the first platform in Canada that lets people pay nearly any bill with a credit card while unlocking cashback, points and financial flexibility. Billions in payments move through Chexy, our customer base is growing fast, and we've just relaunched the brand. Over the next 12 months we launch several new products, starting with our first credit card in Q1 2027.

We're backed by Khosla Ventures, Crossbeam Venture Partners, Venrex and we partner with Aeroplan and other leading Canadian financial and telecom brands.

About the role
Chexy is hiring its first CMO / Head of Marketing to own how Canadians come to know, try and stick with Chexy. You report to the CEO, sit on the leadership team, and own the consumer growth and brand number: acquisition, activation, retention and the brand's place in the market. You take a newly relaunched brand and a pipeline of product launches, including our first credit card in Q1 2027, and turn them into growth.

This is a hands-on executive role in a small company. You set the consumer marketing plan, the budget and the hiring plan behind it, and you build and lead a team of senior individual contributors and the AI agent stack they run on. No layers of managers, no junior staff, no large agency roster. Agents do the production and analysis. Your team does the judgment, taste and strategy.

You own the outcome.

We need someone who can scale channels, lead senior ICs, own the numbers and the brand's place in the market, and still get their hands dirty testing growth hacks and ideas no Canadian fintech has tried.

We care about taste, speed and results.

What you'll own
The number

Consumer acquisition, activation and retention targets, CAC and payback, and the marketing budget

The weekly growth read: what's working, what isn't, where the next dollar goes

Measurement: incrementality tests and a view of what is actually moving the business, not what the ad platforms report

Experiments

A constant pipeline of growth experiments: referral mechanics, contests, partnership activations, unconventional channels and ideas no Canadian fintech has tried

Fast kills and fast scaling: what wins expands across channels within weeks

Brand and positioning

The Chexy brand in market after the 2026 relaunch: voice, creative standard, and consistency across paid, organic, lifecycle, partnerships, PR and web

Positioning and messaging for the core product and every new launch

Product marketing. There is no separate PMM function; you own how we describe what we sell

Launches

Go-to-market for every product launch over the next 12 months, starting with our first credit card in Q1 2027

Launches that feel like moments, not feature announcements

Lifecycle

Activation, cross-sell into premium tiers and new products, and churn saves

The journey logic and guardrails. Agents draft and execute

Partners, creators and press

Co-marketing with Aeroplan and our bank and telecom partners, including the brand and legal reviews that come with them

The creator and referral programs

PR and communications, with the founders

Team and systems

The consumer marketing plan, budget and hiring plan: you decide what the team needs to be and you build it

Leading senior ICs who build their own agents and automations

The marketing agent stack, with engineering: data layer, creative pipeline, lifecycle automation, experimentation, reporting

Agencies and contractors, used for specialist work only

Marketing compliance in a regulated category: every claim gets reviewed, and you make that fast rather than slow

What success looks like
Twelve months in:

CAC and payback are at or better than plan, with incrementality tests behind the numbers rather than platform-reported attribution

Our first credit card has launched with a go-to-market that partners and the board point to as the standard for what comes next

Canadians increasingly recognize Chexy unprompted. Awareness and consideration are measured and moving

Paid, organic, lifecycle, partnerships and web feel like one brand

A team of senior ICs is in place, sized to the plan you set, each shipping weekly, with agents doing most of the production and analysis

New…