Senior Manager, Lifecycle Marketing

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 and Venrex, and we partner with Aeroplan and other leading Canadian financial and telecom brands.

About the role

Chexy is hiring a Senior Manager, Lifecycle Marketing to own every message that leaves the app and the numbers behind them. You report to the CMO and own lifecycle end to end: the sequences that bring non-activators back, engagement around each monthly payment, retention and churn saves, and, for every new line we launch, marketing it to our existing base and the upsell number that comes with it, starting with our first credit card in Q1 2027.

Launches to the base are yours. For each new product you decide who gets it first, the offer, the waitlist and early-access sequence, launch day, the 90-day follow-up, and the cross-sell journeys that run after. You feed positioning with what you know about the base; the CMO owns the positioning itself.

You run on agents. Segmentation, journey builds, copy variants, send-time optimization and reporting are done by agents you build and supervise. Your job is deciding what we say, to whom, when, and what it's worth.

We care about taste, speed and results.

What you'll own

Activation recovery

• Day 1 to day 30 sequences for people who signed up and haven't paid a bill yet: triggered by drop-off step, segmented by bill type and customer segment, with offer and timing tests running continuously
• Win-back offers and their economics, with a budget line agreed with finance

Engagement and retention

• The monthly rhythm: reminders, confirmations, rewards moments and what sits around each payment
• Churn risk and saves: who is at risk, why, and what brings them back

Upsell

• Cross-sell into premium tiers and new products, and the upsell number for each
• The cross-sell journeys that run after every launch: who, when, what offer

Launches to the base

• For every new line, the existing-customer go-to-market: who gets it first, the offer, the waitlist and early-access sequence, launch day, the 90-day follow-up
• The upsell number for each launch, starting with our first credit card in Q1 2027
• Input to positioning from what you know about the base: which segment bites, what objection shows up in support

Channels, cadence and caps

• Push, email, SMS and in-app: what goes where, how often, and the caps across channels so nobody gets four nudges in a day
• The notification taxonomy with product (transactional, behavioural, promotional), opt-in strategy, deliverability
• Opt-out and uninstall rates, reviewed weekly

Measurement

• Holdouts on every major program: incremental impact, not open rates
• The weekly lifecycle read to the CMO

Your agents

• Segmentation and audience builds, journey builds, copy variants, send-time optimization, fatigue flags, reporting

Compliance

• CASL consent and unsubscribe handling, claims review, Québec French where it applies. Agents check first, humans sign off

What success looks like

Twelve months in:

• Thirty-day activation is up, with holdouts proving your sequences did it
• Every new line has launched to the base with a plan, an offer and an upsell number, and hit it or taught us why not
• Cross-sell into premium tiers and the card runs on journeys, not one-off blasts, and converts at the rate the plan assumes
• Churn saves have a measured impact, and the at-risk model is yours
• The credit card launch reaches the base as a sequence of moments, with every message in place before launch day
• Opt-out and uninstall rates are flat or down while send volume is up
• A notification taxonomy and cap policy exists, agreed with product and revisited quarterly
• Agents run the builds, variants and reporting; your time goes to journey design and offers

What we're looking for

• 5+ years in lifecycle, CRM or retention marketing at a consumer app, fintech, telco or subscription business, including at least one product launch to an existing base
• You have launched a product to an existing base and owned the upsell or adoption number: the plan, the offer, the sequence, and what it did
• You have owned a lifecycle program end to end in Braze, Customer.io, Iterable or similar: journey logic, segmentation, cadence and caps, not just the copy
• You have run holdouts and can tell us the incremental impact of a program you owned, and about one that didn't work
• You know push: opt-in strategy, frequency, deep links, and what drives uninstalls
• You write SQL and build your own segments; you build automations and agents (Braze Canvas with APIs, n8n, Zapier, LLM tools) and use them daily
• You write well enough to draft the message yourself when the agent's variant misses
• You have worked in a regulated or claims-sensitive category (CASL, financial promotions), or can show you'll learn it fast

Strong plus: fintech or payments; offer and incentive economics; Canadian market; French.

This probably isn't the role for you if

• Lifecycle to you means writing emails while someone else builds the journeys
• You have never owned a launch to an existing base, only sent the announcement
• You have never run a holdout and report on open rates
• You need a CRM admin, an analyst and a copywriter before you can ship
• You think a launch is a single announcement email
• AI on your resume means ChatGPT for subject lines

Why join Chexy?

• Own the whole journey: every message to every customer, and every launch to the base
• A launch worth owning: our first credit card to an engaged base in Q1 2027, with more to follow
• A product with a built-in rhythm: monthly bills give lifecycle something to work with that most apps don't have
• Work the way lifecycle is going to work: agents on builds and variants, you on journeys and offers
• Work with the CMO and the founders: small team, fast decisions
• Equity: meaningful equity in a high-growth fintech
• Toronto office: we work in-office 5 days a week

How we hire

We 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 a lifecycle program you owned end to end with its holdout result, a launch you ran to an existing base and what it did to upsell, and an agent or automation you built that runs part of your work without you.

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.