SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Chexy is a Canadian fintech platform that transforms major bills (rent, mortgages, tuition, insurance) into opportunities to earn rewards and improve cash flow. The company has just relaunched its brand and is backed by Khosla Ventures, Crossbeam Venture Partners, and Venrex, with partnerships including Aeroplan. Billions in payments move through the platform, and the company is launching several new products over the next 12 months, including its first credit card in Q1 2027.
As CMO/Head of Marketing, you will be Chexy's first marketing leader, reporting directly to the CEO and sitting on the leadership team. You own all aspects of consumer growth and brand strategy: acquisition, activation, retention, and the brand's market position.
Key responsibilities include:
**Growth & Numbers**: Own consumer acquisition, activation, and retention targets; manage CAC and payback metrics; control the marketing budget; conduct weekly growth analysis to identify what's working and where to allocate spend next; run incrementality tests to measure true business impact beyond platform attribution.
**Experimentation**: Build a constant pipeline of growth experiments including referral mechanics, contests, partnership activations, and unconventional channels. Execute fast kills and rapid scaling—winning ideas expand across channels within weeks.
**Brand & Positioning**: Establish Chexy's brand voice, creative standards, and consistency across paid, organic, lifecycle, partnerships, PR, and web following the 2026 relaunch. Own product marketing and positioning for the core product and all new launches.
**Product Launches**: Lead go-to-market strategy for every product launch over the next 12 months, starting with the credit card in Q1 2027. Create launches that feel like cultural moments, not feature announcements.
**Lifecycle Marketing**: Drive activation, cross-sell into premium tiers, and churn prevention. Design journey logic and guardrails (with agents handling execution).
**Partnerships & Communications**: Manage co-marketing with Aeroplan, bank, and telecom partners, including brand and legal reviews. Oversee creator and referral programs, PR, and communications.
**Team & Systems**: Build and lead a team of senior individual contributors (no layers of managers, no junior staff). Design the marketing agent stack with engineering, covering data layer, creative pipeline, lifecycle automation, experimentation, and reporting. Manage compliance in a regulated category.
This is a hands-on executive role. You set strategy and own outcomes, but you also write briefs, evaluate creative, read dashboards, and test growth ideas yourself. AI agents handle production and analysis; your team provides judgment, taste, and strategy.
Success metrics at 12 months: CAC and payback at or better than plan with incrementality tests backing attribution; credit card launch with go-to-market the board points to as the standard; unprompted Chexy awareness and consideration growing; paid, organic, lifecycle, partnerships, and web feeling like one cohesive brand; senior IC team shipping weekly with agents handling most production; new creative and experiments reaching market every week; partner campaigns shipping on time; agency and contractor spend lower than today with higher output.
**Requirements**
- 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 (challenger telco, neobank, fintech, consumer subscription, or DTC brand)
- Owned a real number and real budget; can demonstrate what happened to CAC, payback, and growth during your tenure
- Scaled channels: taken paid, referral, partnerships, or organic from small to meaningful share of growth; understand what breaks at each stage
- Built or rebuilt a marketing function around AI agents and automation; can articulate exactly what agents did, which tools were used, what headcount or agency spend was replaced, and what broke
- Both brand instinct and performance rigor: comfortable reading dashboards and judging creative
- Led senior individual contributors: built and run small, senior teams (not large orgs with manager hierarchies); set plan, budget, and hiring
- Still hands-on: write briefs, kill creative, read numbers yourself
- Track record with growth hacks: referral mechanics, contests, partnership stunts, unconventional channels—some of which worked
- Experience in regulated or claims-sensitive categories, 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 language skills; fintech background.
Not a fit if: you prefer leading through managers rather than working alongside a small team; you need a large team or agency roster; you come from brand-only or performance-only backgrounds and want to stay in that lane; your AI experience is strategy-only, not hands-on execution; you need layers of approval before decisions reach customers; you've spent your career at incumbents without winning attention on a limited budget.
