Director of Loyalty & Retention

What We’re Looking For

We’re looking for a Director of Loyalty & Retention to own the strategy and execution of loyalty, lifecycle, and retention initiatives across Phoenix and Raven. This role is critical to maximizing customer lifetime value, reducing churn, and building trust-driven, long-term patient relationships in a discretion-based, medical context.

This role offers end-to-end ownership of cross-brand loyalty programs, lifecycle journeys, communication frameworks, and personalized experiences, with broad influence across CRM, product, content, and patient experience. You’ll set the vision and roadmap for how loyalty shows up across the patient journey while ensuring strong operational execution across CRM, product, content, and the patient experience. This is a highly senior, strategic leadership opportunity for someone who has fully owned the function before, brings a deep understanding of trust, empathy, privacy, and timing, and is excited to redefine what loyalty can look and feel like in healthcare.

What You’ll Do

Loyalty & Retention Strategy

• Build a multi-year loyalty and retention roadmap for Phoenix and Raven, including program design, membership tiers, benefits, incentives, and unique value-adds.

• Define the loyalty value proposition in a category where discretion, emotional trust, and personal outcomes matter as much as traditional rewards.

• Establish a clear framework for measuring LTV, retention, and customer health metrics with supporting hypotheses and experimentation plans.

Lifecycle Marketing & Communication

• Own the full customer communication ecosystem, from onboarding through long-term engagement, across email, SMS, in-app messaging, and offline touchpoints.

• Craft emotionally intelligent, privacy-safe messaging that resonates with sensitive patient needs and reflects our brand values.

• Design and deploy segmented lifecycle journeys tailored to condition, treatment stage, sentiment, and behavioral signals.

Program Management & Innovation

• Conceptualize and launch loyalty programs that serve as true differentiators; integrating education, clinical confidence, community, access, and personalized care.

• Collaborate closely with product, care teams, clinical operations, and marketing to ensure programs deliver real value and are operationally sound.

• Lead cross-functional execution of retention experiments, from A/B tests to full-scale program rollouts.

Analytics & Performance Management

• Own retention KPIs across brands and programs.

• Partner with customer service, ops, and other teams to understand behavioral cohorts, and identify high-leverage retention opportunities.

• Translate complex data into clear insights, decision frameworks, and action plans.

Team Leadership & Cross-Functional Influence

• Build and lead a high-performing loyalty, retention, and lifecycle team.

• Serve as the internal expert and educator on customer loyalty: helping shift the organizational mindset from transactional to relational engagement.

• Build and maintain strong partnerships with product, engineering, care delivery, creative, compliance, and the executive team.

Bring Success To This Role

• Increase retention and lifetime value across patient cohorts and conditions.

• Create a loyalty experience that patients genuinely value and trust and that differentiates Phoenix and Raven in the market.

• Design a cohesive, data-driven communication system that guides patients through every stage of their journey.

• Generate a measurable reduction in churn and a meaningful increase in engagement, satisfaction, and repeat treatment rates.

What You’ll Bring

• 8+ years in retention, lifecycle, loyalty, CRM, or customer marketing roles, with at least 3+ years in a leadership position.

• Proven track record building loyalty programs or high-performing retention functions: ideally in health, wellness, DTC, subscription, e-commerce, or other sensitive-decision categories.

• Expert-level understanding of customer segmentation, lifecycle frameworks, and LTV economics.

• Deep familiarity with CRM platforms, customer data infrastructure, experimentation tools, and personalization engines.

• Ability to blend qualitative insights (human behavior, patient psychology) with quantitative rigor.

• Empathy-driven marketer mindset with an instinct for privacy-safe communication and emotional nuance.

• Creative, first-principles thinking and ability to redefine what loyalty means in a discretion-based medical context.

• Exceptional communication and collaboration skills, allowing you to build alignment, shape perspective, and lead change across diverse teams and leadership levels.

• Comfortability working in a fast-paced, evolving startup environment.

• Nice to Haves

• Experience operating in regulated, privacy-centric, or clinical environments.

• Experience with Klaviyo.

Why Work at Phoenix?

• A Rewarding Mission: Through our asynchronous care model, Phoenix is reimagining patient-centric care for Canadians across the country by making diagnoses and treatment delivery faster, more accessible, and completely discreet.

• Impact & Autonomy: You’ll work directly with passionate, experienced leaders who’ve seen the ups and downs of building a business and genuinely care about your growth. You won’t just execute — you’ll help shape the future of Phoenix and Raven.

• Collaborative In-Office Culture: Based in the heart of downtown Toronto, our HQ team comes together on-site five days a week to build fast and push what’s possible. We love the fast feedback loops, spontaneous brainstorms, and actually knowing the people we work with. Bonus points if you’re into the occasional foosball tournament or have strong opinions about the best lunch spot in the neighbourhood.

• Competitive Pay, Real Benefits: Our compensation bands are backed by real market data, so offers are competitive and fair. Our benefits package includes standard healthcare coverage, a remote-first holiday season, and holistic wellbeing support — such as a wellbeing allowance and flexible additional time off to care for loved ones, support mental health, observe meaningful religious and cultural holidays, or when life just happens.

Phoenix is an Equal Opportunity Employer. In accordance with the Accessibility for Ontarians with Disabilities Act, 2005 and the Ontario Human Rights Code, Phoenix will provide accommodations to applicants with disabilities throughout the recruitment, selection, and/or assessment process. If selected to participate in the recruitment, selection, and/or assessment process, please inform Human Resources staff of the nature of any accommodation(s) that you may require.

Phoenix uses artificial intelligence (AI) to help review applications and screen resumes during the early stages of our hiring process. These tools assist our recruitment team, and all final hiring decisions are made by real people — not by automated systems.

Thank you for your interest in joining the Phoenix team! While we are lucky to attract a high level of interest in each of our roles, only candidates selected for an interview will be contacted.