Lifecycle & Retention Lead

Office-first - Toronto, Canada

$90,000 - $140,000 + equity

Your opportunity

We’re supporting a fast-growing Canadian fintech that has reimagined how people manage their largest recurring expenses and is focused on helping them gain more value from every dollar spent. Already processing over a billion dollars in annual payment volume and serving a rapidly expanding user base, the team is building critical financial infrastructure that demands robust, secure, and scalable systems.

As the platform continues to grow, long-term success increasingly depends on how effectively customers are activated, educated, and retained over time. Lifecycle performance sits at the center of product adoption, trust, and repeat usage.

This role is designed to own the customer journey end to end, from first interaction through habitual usage and long-term retention. It is a senior individual contributor position with broad cross-functional ownership and a clear path to building and scaling a dedicated lifecycle or CRM function as the company grows.

Key responsibilities 

  • Lifecycle strategy ownership: Own the end-to-end lifecycle strategy across onboarding, activation, engagement, retention, reactivation, and winback

  • Product partnership: Partner closely with Product to improve conversion and activation through in-product journeys, education, prompts, and optimized user flows

  • Lifecycle programs: Design and operate lifecycle messaging across email, in-app, push, and SMS, with channel selection informed by product context and compliance requirements

  • Segmentation and personalization: Build and maintain behavioural, cohort-based, and value-based segmentation frameworks to drive relevance and reduce message fatigue

  • Experimentation and optimization: Establish and run a structured experimentation engine using A/B tests, holdouts, and cohort analysis tied to real retention and churn outcomes

  • Churn ownership: Lead churn monitoring and root-cause analysis using retention curves, leading indicators, cancellation signals where applicable, and qualitative feedback loops

  • Behavioural strategy: Define lifecycle north-star behaviours and next-best-action strategies that drive repeat usage and long-term customer value

  • Data foundations: Collaborate with Data and Engineering on event tracking, customer states, and data pipelines to ensure lifecycle programs are reliable and measurable

  • Roadmap and scale: Own the lifecycle roadmap and operating cadence, and over time hire and scale lifecycle specialists across CRM operations, analytics, and messaging

Your know-how

  • 5-10 years of experience in lifecycle, CRM, or retention roles within consumer technology, fintech, or subscription-based companies

  • Demonstrated success improving activation, retention, and churn through structured lifecycle programs and close collaboration with product teams

  • Strong analytical capabilities, with comfort working in funnels, cohorts, experimentation design, and retention curve analysis

  • Practical technical fluency, including the ability to partner effectively with engineers on event schemas, data quality, and journey logic

  • Strong instincts for customer messaging and copy quality, with the ability to set direction and maintain high standards

  • Experience building lifecycle foundations from scratch, including tooling, templates, QA processes, deliverability practices, governance, and measurement frameworks

It’s a bonus if

  • You have hands-on experience with lifecycle platforms such as Customer.io, Klaviyo, or similar tools, as well as CDPs like Segment

  • Your background includes building retention loops in fintech or fintech-adjacent products where trust, education, frequency, and habit formation are core to engagement

Interested in learning more?

Please send your resume or LinkedIn profile URL to talent@lutrapartners.com with “Lifecycle & Retention Lead” as the subject line. One of our talent partners will be in contact shortly.