Head of Retention, DTC Subscription

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 Retention, DTC Subscription based in Canada.

We are seeking an experienced retention leader to take full ownership of subscription growth, lifecycle marketing, and customer experience across two direct-to-consumer brands. This strategic yet hands-on role will focus on reducing churn, increasing customer lifetime value, and building stronger relationships throughout the customer journey. You will lead subscription initiatives, email and SMS marketing, post-purchase experiences, and customer support operations. Working closely with the founder and senior leadership team, you will turn customer insights and performance data into measurable growth opportunities. The environment is fully remote, fast-paced, and highly entrepreneurial, offering significant autonomy and direct influence on business performance. This is an opportunity to shape the retention strategy of a rapidly scaling business and help drive its next stage of growth.

Accountabilities:

• Own the subscription programs across both brands, including offers, bundles, subscription cadence, customer portals, and cancellation flows.

• Develop and test retention initiatives such as save offers, skip, swap and pause options, and win-back campaigns to reduce churn and increase subscriber value.

• Lead email and SMS strategy, oversee lifecycle campaigns, manage the retention agency, and maintain strong list health and deliverability.

• Build and optimize the full customer lifecycle, from welcome and post-purchase journeys to replenishment, cross-sell, loyalty, VIP, and win-back programs.

• Improve the post-purchase experience by analyzing cancellation reasons, customer reviews, surveys, and support interactions to identify and address retention issues.

• Lead the customer experience team, establish customer service policies, and monitor key performance indicators including CSAT, response times, refunds, and chargebacks.

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

• Run regular retention reviews with senior leadership, identify the highest-impact growth opportunities, and document processes and standard operating procedures.

• Collaborate with growth and brand teams on promotional campaigns, launches, and initiatives that increase subscription adoption and customer loyalty.

• Maintain a consistent testing and optimization rhythm, using data, automation, and AI tools to improve performance and operational efficiency.

Requirements:

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

• Essential 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.

• Hands-on experience developing and managing email and SMS marketing programs using Klaviyo or a comparable platform.

• Deep familiarity with Loop or a similar subscription management platform.

• Proven ability to lead retention and customer experience teams, manage external agencies, and drive performance through clear KPIs.

• Strong analytical skills, with the ability to interpret retention, churn, and lifetime value data and translate findings into actionable initiatives.

• Experience designing, running, and evaluating structured tests across offers, customer journeys, and retention tactics.

• Commercial judgment and a strong understanding of profitability, margins, and the economics of discounts and save offers.

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

• Fluent English communication skills.

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

• Strong alignment with a culture built around continuous improvement, speed, smart execution, and consistently exceeding expectations.

• Motivated to work closely with the founder and contribute directly to the growth of a scaling 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 and influence over the retention strategy and customer experience across two brands.

• Opportunity to contribute to the growth of a profitable, rapidly scaling direct-to-consumer business.