Head of Retention ($20M+ Ecommerce)

Everstride is a rapidly growing DTC ecommerce brand operating at a $20M+ annual run rate. We make compression socks for women who have been let down by the category — women in their 50s, 60s and beyond with swollen, painful legs, and a drawer full of other brands they gave up on. As Head of Retention, you'll own everything that happens after the first click. Email, SMS, lifecycle, repeat purchase rate, AOV, LTV, community and subscription. This is an exciting role for an A player — we have the perfect environment to grow in. Company: Everstride Website: www.everstridesocks.com Language: English Availability: 35+ hours / week (exclusive) Working Time Zone: CET Work Type: Full-Time, Remote Payment: $8,000 - $10,000+ USD per month, plus bonuses ### Responsibilities - Own LTV, repeat purchase rate and email/SMS revenue as your headline numbers - Manage the full relationship and strategy for our email agency, ramping campaign volume and holding them to a standard - Write and direct the copy — you'll be the voice speaking to our customer, whether you're writing it yourself or setting the bar for the agency - Rebuild and continuously test our flow architecture: welcome, abandoned cart, post-purchase, winback, replenishment and VIP - Improve retention specifically in the 30 and 90 day windows after first purchase, where the compounding happens - Grow the email and SMS list actively — popups, lead magnets, quizzes, offers, paid capture, whatever works - Investigate the opportunity of subscriptions for Everstride - Build and nurture a genuine customer community, in whatever form serves our audience best: VIP lists, a Facebook group, subscriber tiers, reviews and UGC - Collaborate closely with our CRO agency on website funnels, landing pages and offers that lift AOV and LTV - Report monthly on retention performance with a clear narrative — what moved, why, and what you're doing next - Recruit and build a team beneath you as the function grows ### Must-Haves - Exceptional copywriting skills — you write emails and copy that converts, and you can write warmly to a 60-year-old woman without sounding clinical or patronising. This is non-negotiable for the role. - Deep, hands-on Klaviyo experience — you build in the platform, you don't just approve someone else's work - Strong grasp of retention and lifecycle strategy: segmentation, cohorts, replenishment cycles, winback - Genuine financial literacy — you can pull, read and act on LTV, CAC, margin and cohort data without waiting for a report - Proven experience managing external agencies — you set expectations, approve work and drive results - Highly organised with sharp presentation of your work and thinking; you track multiple workstreams and stay on top of them without being chased - Ability to hire and onboard support when growth requires it - Self-directed and genuinely autonomous — we're remote and lean, and nobody will be managing your calendar ### Nice To Haves - Experience working with 8 or 9-figure DTC brands — strongly preferred - Background at a retention or email agency, now looking to move brand-side and own the function properly - Experience launching or managing a subscription programme - Experience with an older or health-adjacent customer base - Hands-on experience and genuine enthusiasm for AI tools and how they accelerate marketing workflows - CRO or conversion optimisation experience — if you're strong here, the scope of this role grows ### Benefits - Full-time role aligned to CET time zone - Remote setup with flexible hours (freelance remote position) - Direct collaboration with the founder, with high ownership and real impact - Own an entire function at a fast-growing brand rather than one channel at an agency - Performance bonuses tied to the growth you create - Opportunity to build a team beneath you as the function scales