VP Marketing

King Street East, Toronto, Ontario, Canada, M5A 1L3full-time. October 20, 2026DescriptionAbout 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 a

VP 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 senior leadership 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 numberConsumer acquisition, activation and retention targets, CAC and payback, and the marketing budgetThe weekly growth read: what's working, what isn't, where the next dollar goesMeasurement: incrementality tests and a view of what is actually moving the business, not what the ad platforms reportExperimentsA constant pipeline of growth experiments: referral mechanics, contests, partnership activations, unconventional channels and ideas no Canadian fintech has triedFast kills and fast scaling: what wins expands across channels within weeksBrand and positioningThe Chexy brand in market after the 2026 relaunch: voice, creative standard, and consistency across paid, organic, lifecycle, partnerships, PR and webPositioning and messaging for the core product and every new launchProduct marketing. There is no separate PMM function;

you own how we describewhat we sellLaunchesGo-to-market for every product launch over the next 12 months,



starting with our first credit card in Q1 2027Launches that feel like moments, not feature announcementsLifecycleActivation, cross-sell into premium tiers and new products, and churn savesThe journey logic and guardrails. Agents draft and executePartners, creators and pressCo-marketing with Aeroplan and our bank and telecom partners, including the brand and legal reviews that come with themThe creator and referral programsPR and communications, with the foundersTeam and systemsThe consumer marketing plan, budget and hiring plan: you decide what the team needs to be and you build itLeading senior ICs who build their own agents and automationsThe marketing agent stack, with engineering: data layer, creative pipeline, lifecycle automation, experimentation, reportingAgencies and contractors, used for specialist work onlyMarketing compliance in a regulated category: every claim gets reviewed, and you make that fast rather than slowWhat 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 attributionOur first credit card has launched with a go-to-market that partners and the board point to as the standard for what comes nextCanadians increasingly recognize Chexy unprompted. Awareness and consideration are measured and movingPaid, organic, lifecycle, partnerships and web feel like one brandA team of senior ICs is in place, sized to the plan you set, each shipping weekly, with agents doing most of the production and analysisNew creative and experiments reach market every week, and the weekly growth read tells the company what won, what lost and what's nextPartner co-marketing campaigns ship on time and get through partner reviews without dramaAgency and contractor spend is lower than today and output is higherWhat 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 brandYou owned a real number and a real budget, and can show what happened to CAC, payback and growth while you held itYou have scaled channels: taken paid, referral, partnerships or organic from small to a meaningful share of growth, and you know what breaks at each stageYou 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 wayBoth 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 creativeYou 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 themYou are still hands-on. You write briefs, kill creative and read the numbers yourselfYou like growth hacks.

Referral mechanics, contests, partnership stunts, unconventional channels: you have a record of trying things, and some of them workedExperience in a regulated or claims-sensitive category, or with large partners whose legal and brand teams review everythingStrong 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 teamYou need a large team or agency roster to functionYou come from brand only or performance only and want to stay in that laneYour experience with AI is a strategy deck, not a function you built and ranYou want every decision to go through layers of approval before it reaches customersYou have spent your career at incumbents and have never had to win attention without a big budgetWhy join Chexy?

Build a category-defining consumer brand:

shape how Canadians think about the biggest payments in their livesOwn the number and the brand:

one leader, one view of the P&L;, no split between brand and growthLaunch real products:

our first credit card ships in Q1 2027, with more to followWork the way marketing is going to work:

a senior team running on AI agents, designed and built by youWork directly with the founders:

a seat on the leadership team and real influence on company strategyEquity:

meaningful equity in a high-growth fintechToronto office:

we work in-office 5 days a weekHow we hire

We keep our hiring process transparent 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.

📌 Vp Marketing (Winnipeg)
🏢 Chexy
📍 Winnipeg