Head of Lifecycle & Customer Experience

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Head of Lifecycle & Customer Experience based in Canada.

We are looking for a senior lifecycle and customer experience leader to own the entire customer journey beyond the first purchase across two direct-to-consumer brands. In this high-impact role, you will shape subscription strategy, lifecycle marketing, post-purchase engagement, and customer support operations. Your mission will be to reduce churn, increase customer lifetime value, and build experiences that turn first-time buyers into loyal customers. You will combine strategic leadership with hands-on execution, using customer insights, data, testing, and automation to drive measurable results. Working closely with the founder and senior leadership team, you will help scale a fast-growing business toward its next stage of growth. This is a fully remote opportunity within a lean, ambitious, and fast-paced environment where ownership, speed, and continuous improvement are highly valued.

Accountabilities

• Lead the subscription programs across both brands, overseeing offers, bundles, subscription cadence, customer portals, and cancellation journeys.

• Develop and test retention initiatives, including save offers, skip, swap and pause options, and win-back campaigns to reduce churn and improve subscriber retention.

• Own email and SMS marketing strategy, manage the retention agency, oversee campaign calendars and lifecycle flows, and maintain strong list health and deliverability.

• Build and optimize the complete customer lifecycle, including welcome, post-purchase, replenishment, cross-sell, win-back, loyalty, and VIP journeys.

• Improve the post-purchase experience by analyzing cancellation reasons, customer reviews, surveys, and support interactions, then coordinating solutions with relevant teams.

• Lead the customer experience function, manage the Customer Experience Manager, establish customer service policies, and monitor key metrics such as CSAT, response times, AI resolution rate, refunds, and chargebacks.

• Track subscription performance, monthly recurring revenue, churn, save rates, repeat purchase rates, cohort retention, and customer lifetime value by brand and channel.

• Establish a consistent testing and optimization process, ensuring that retention initiatives are measured, documented, and improved continuously.

• Collaborate with growth and brand leadership on promotional campaigns, product launches, and initiatives that increase subscription adoption and customer engagement.

• Lead regular retention performance reviews, identify the most important growth opportunities, and develop standard operating procedures to ensure sustainable execution.

Requirements:

• 5–6+ years of experience in retention or lifecycle marketing within direct-to-consumer businesses.

• Essential: previous experience leading retention for a subscription-based brand generating at least $30–50M in annual revenue, ideally at nine-figure scale.

• Strong expertise in subscription growth, churn reduction, save strategies, cohort analysis, and monthly recurring revenue.

• Proven ability to develop and manage email and SMS programs using Klaviyo or a comparable lifecycle marketing platform.

• Hands-on experience with Loop or a similar subscription management platform.

• Demonstrated leadership experience managing retention and customer experience teams, as well as external agencies.

• Strong analytical capabilities, with the ability to interpret customer, cohort, churn, and lifetime value data and translate insights into measurable improvements.

• Experience designing, running, and evaluating structured tests across subscription offers, lifecycle flows, and retention strategies.

• Strong commercial judgment and an understanding of profitability, margins, and the financial impact of discounts and retention incentives.

• Customer-focused mindset, with the ability to identify the underlying reasons customers stay, disengage, or cancel.

• Excellent communication skills and fluency in English.

• Comfortable working in a fully remote, fast-paced environment with significant ownership, accountability, and autonomy.

• Strong alignment with a culture of continuous improvement, speed, resourcefulness, data-driven decision-making, and high performance.

• Motivated to work closely with the founder and play a meaningful role in scaling a growing business.

Benefits:

• Fully remote position, open to candidates based outside the United States.

• Annual salary of USD $115,000–$145,000, depending on experience and expertise.

• Performance bonus of 15–20% of base salary after the trial period.

• Direct collaboration with the founder and senior leadership team.

• Significant ownership of lifecycle marketing, retention, and customer experience strategy across two brands.

• Opportunity to make a measurable impact on the growth of a profitable, rapidly scaling direct-to-consumer business.