Chief Marketing Officer

CMO/Head of MarketingKing Street East, Toronto, Ontario, Canada, M5A 1L3 full-time. October 11, 2026
About ChexyAt 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 roleChexy 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 ownThe 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 describewhat 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 likeTwelve 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 creative and experiments reach market every week, and the weekly growth read tells the company what won, what lost and what's next
Partner co-marketing campaigns ship on time and get through partner reviews without drama
Agency and contractor spend is lower than today and output is higher
What we're looking for
7+ years in consumer marketing, with at least one stretch owning marketing end to end (brand, performance, lifecycle, PR) at a company that took share from incumbents: a challenger telco, neobank, fintech, consumer subscription or DTC brand
You owned a real number and a real budget, and can show what happened to CAC, payback and growth while you held it
You have scaled channels: taken paid, referral, partnerships or organic from small to a meaningful share of growth, and you know what breaks at each stage
You have already built or rebuilt a marketing function around AI agents and automation, and can tell us exactly what the agents did, which tools you used, what headcount or agency spend it replaced and what broke along the way
Both brand instinct and performance rigour. The team is too small for a brand leader who can't read a dashboard or a performance leader who can't judge creative
You have led senior ICs: built and run small, senior teams rather than large orgs with managers of managers, and set the plan, budget and hiring behind them
You are still hands-on. You write briefs, kill creative and read the numbers yourself
You like growth hacks. Referral mechanics, contests, partnership stunts, unconventional channels: you have a record of trying things, and some of them worked
Experience in a regulated or claims-sensitive category, or with large partners whose legal and brand teams review everything
Strong plus: Canadian consumer market experience;
co-marketing with loyalty programs, banks or telcos;
referral, contest or creator-led growth;
French;
fintech.
This probably isn't the role for you if
You want to lead through managers rather than do the work alongside a small team
You need a large team or agency roster to function
You come from brand only or performance only and want to stay in that lane
Your experience with AI is a strategy deck, not a function you built and ran
You want every decision to go through layers of approval before it reaches customers
You have spent your career at incumbents and have never had to win attention without a big budget
Why join Chexy?
Build a category-defining consumer brand:
shape how Canadians think about the biggest payments in their lives
Own the number and the brand:
one leader, one view of the P&L, no split between brand and growth
Launch real products:
our first credit card ships in Q1 2027, with more to follow
Work the way marketing is going to work:
a senior team running on AI agents, designed and built by you
Work directly with the founders:
a seat on the leadership team and real influence on company strategy
Equity:
meaningful equity in a high-growth fintech
Toronto office:
we work in-office 5 days a week
How we hireWe keep our hiring process clear and human. You'll go through a mix of conversational interviews and practical discussions designed to show how you think, what you've built and how you work with others. Expect to walk us through the marketing function you built with AI, the number you owned and what happened to it, and how you would set the plan, budget and team here.
We use AI tools to help us organize and review applications;
every decision about who we interview and who we hire is made by a person. This posting is for an existing vacancy. If you interview with us, we'll let you know within days of your last interview whether a decision has been made.
Chexy is an equal opportunity employer. If you require any accommodations or support during the hiring process, let us know and we'll do our best to help.
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