Responsibilities

• Lead portfolio of subscription clients as the senior strategist of record and be the day-to-day retention lead for up to eight brands.
• Run client calls, write the briefs, pressure-test the data, and partner with platform vendors and internal teams to bring the work to life.
• Mentor junior strategists and contribute to playbooks and frameworks that make our work repeatable.
• Report directly to the Founder and CEO and work alongside a small, senior team of strategists, analysts, and platform specialists.
• Serve as the senior retention lead for four to six subscription brands. Run weekly working sessions, monthly business reviews, and ad-hoc strategy calls with founders, CMOs, and growth and CX leadership.
• Analyze cohort retention curves, churn drivers, cancel flow save rates, dunning recovery, LTV by acquisition source, and lifecycle gap analysis.
• Translate the diagnosis into a prioritized retention roadmap.
• Design 30/60/90 day retention roadmaps, cancel flow strategies, post-purchase and winback flows, gifting and loyalty programs, quarterly upsell mechanics, and subscription portal optimizations.
• Communicate strategy clearly to non-retention stakeholders: acquisition leads, CX teams, finance, and founders. Align cross-functional teams behind the work.
• Write detailed briefs for email and SMS flows, cancel surveys, portal banners, post-purchase journeys, and physical inserts; brief copywriters, designers, and developers with enough specificity that the first draft is close to right.
• Partner with subscription platforms (Stay AI, Skio, Recharge) and email platforms (Klaviyo) to scope, build, QA, and launch flows; lead migrations between platforms when required, including subscriber data mapping, flow recreation, and customer communication strategy.
• Set up and monitor reporting on the metrics that matter: retention curves, cancel flow save rate, dunning recovery, gifting ROI, and segmented cohort performance.

Requirements

• Six or more years in DTC retention, lifecycle marketing, or CRM, with at least two to three years specifically in subscription businesses (CPG, supplements, beauty, wellness, or services).
• You have owned retention end-to-end for at least one subscription brand at meaningful scale, in-house or agency-side.
• You know what the numbers look like at the founder-and-CMO level.
• You have led other strategists, analysts, or contractors.

Preferred

• Direct experience leading a Stay AI, Skio, or Recharge migration, including subscriber data mapping and customer communication strategy.
• You’ve diagnosed and resolved an email deliverability incident at scale.
• You’ve built or maintained cohort-based LTV models for finance or investor reporting.
• Direct response copywriting chops. You can write the first draft when you have to.
• You’ve presented retention strategy to a board or investor group.

Benefits

• a benefits package including medical, equipment, and wellness stipends.