Lifecycle & Retention Lead

Antler; Toronto; On-site; CAD 80,000 - 120,000; Full time

Job summary

A fintech startup in Toronto seeks a highly analytical Lifecycle Marketing leader to own end-to-end lifecycle strategy, enhancing customer activation, retention, and churn. This senior individual contributor role involves designing customer journeys, collaborating with product and data teams, and building a lifecycle roadmap. Ideal candidates should have 5-10 years in lifecycle marketing within consumer tech or fintech, with strong analytical and copy instincts. Remote work options may be available.

Qualifications

• 5-10 years in lifecycle/CRM/retention at a consumer tech/fintech/subscription company.
• Proven ability to improve activation, retention, and churn.
• Strong copy and messaging instincts.

Responsibilities

• Own lifecycle strategy from onboarding to retention and reactivation.
• Partner with Product to improve conversion through in-product journeys.
• Create segmentation and personalization frameworks to drive relevance.
• Lead churn monitoring and root cause analysis.

Skills

Analytical thinking

Lifecycles/CRM experience

Collaboration with Product teams

Experimentation design

Data interpretation

Tools

Customer.io

Klaviyo

SQL

Job description

At Chexy, we’re reshaping the way money moves—making payments smarter, faster, and more rewarding.

We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money—helping you get more value from every dollar you spend.

As a high‑growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.

About the role

Chexy is looking for a senior, highly analytical Lifecycle Marketing leader to build and own our lifecycle strategy end-to-end—from a customer’s first moments with Chexy through activation, repeat usage, and long-term retention. You’ll be responsible for designing the journeys, triggers, and messaging that move customers from “interested” to “activated” to “habitual,” using a combination of lifecycle channels (email, in‑app, push/SMS as appropriate) and in-product experiences. This role is ideal for someone who loves digging into funnels and cohort behavior, translating insights into crisp hypotheses, and then shipping experiments that measurably improve conversion and retention.

You’ll work in lockstep with Product, Engineering, and Data to ensure the foundations are strong: clean event tracking, clear customer states, reliable segmentation, and trustworthy measurement. Beyond building the lifecycle “machine,” you’ll be the internal owner of churn monitoring—spotting leading indicators, diagnosing root causes, and partnering cross‑functionally to address them through product improvements and targeted lifecycle programs. This is a very senior individual‑contributor role to start, with the opportunity to build a lifecycle/CRM team as Chexy grows.

What you'll do

• Own Chexy’s end-to-end lifecycle strategy, from first‑touch onboarding to retention, reactivation, and winback.
• Partner with Product to improve conversion and activation through in-product journeys (nudges, education, paywalls/prompts where relevant) and optimized flows.
• Build and run lifecycle messaging programs across email, push, SMS, and in-app (channel mix based on product + compliance).
• Create a segmentation and personalization framework (behavioral, cohort-based, and value-based) to drive relevance and reduce message fatigue.
• Establish a lifecycle experimentation engine: A/B tests, holdouts, cohort tests, and measurement tied to real retention and churn outcomes.
• Lead churn monitoring and root-cause analysis: cohort retention curves, leading indicators, cancellation reasons (if applicable), and qualitative feedback loops.
• Define lifecycle “north star” behaviors and next-best-action strategies to drive repeat value.
• Collaborate with Data/Eng on event tracking, customer states, and data pipelines so lifecycle programs are reliable and measurable.
• Build the lifecycle roadmap, operating cadence, and—over time—hire and scale lifecycle specialists (CRM ops, copy, analytics, marketing ops).

What we are looking for

• 5-10 years in lifecycle/CRM/retention at a consumer tech/fintech/subscription company.
• Proven ability to move activation, retention, and churn through structured lifecycle programs and product collaboration.
• Highly analytical: comfortable with cohorts, funnels, experimentation design, and interpreting retention curves (SQL is a plus).
• Practical technical fluency: you can partner with engineers on event schemas, data quality, and journey logic.
• Strong copy + messaging instincts (you don’t need to be a copywriter, but you can set direction and quality).Experience building lifecycle from scratch: tooling, templates, QA, deliverability, governance, and measurement.

Nice to have

• Hands‑on experience with Customer.io / Klaviyo (or similar), plus Segment/CDPs.
• Experience building retention loops in fintech-like products (trust, education, frequency, habit formation).