Head of Retention
Full-Time (40 Hours/Week) and Remote | US Eastern Time | Long-Term Contract
About the Role
Our client is a fast-growing US-based direct-to-consumer brand at the intersection of beauty, lifestyle, and functional product design, currently operating at an eight-figure annual run rate with a clear trajectory toward $100M. They are hiring a Head of Retention to own email and SMS as a top revenue line, build the full lifecycle engine end-to-end, and compound the program as the business scales. This is a builder's seat with real authority — you will report to the Head of Marketing, direct a small team of designers and specialists, and be measured directly on retention revenue, LTV, and repeat purchase rate.
Key Responsibilities
- Own retention strategy and revenue — email and SMS contribution to total revenue, flow revenue, campaign revenue, repeat purchase rate, and 90-day retention
- Build and optimize complete email and SMS flow sets across every product funnel and paid landing page simultaneously (welcome, abandoned cart, browse abandon, checkout, post-purchase, win-back, and the full 90-day LTV journey)
- Own sitewide opt-in coverage — every paid landing page with its full flow set tagged to its opt-in, including technical integrity of subscriber entry and tracking
- Design and evolve a sophisticated segmentation strategy by product interest, behavior, and value, paired with strong list health and deliverability management
- Own the full monthly calendar end-to-end — daily email plus weekly SMS plan, including segmentation, exclusions, offers, send times, and forecasted revenue per send
- Design and run the QA system that keeps every send on-brand, accurate, and on-offer before it ships
- Hold brand voice and editorial craft across the entire program — cultural fluency, nuance, and the ability to make the customer feel seen
- Build AI-driven automations for QA, segmentation, reporting, competitor monitoring, and campaign generation on top of proprietary infrastructure
- Run a structured weekly testing program across subject lines, segmentation, timing, content angles, and flow triggers — codify wins and carry learnings forward
- Own revenue forecasting per send and per flow, reviewed against actuals, plus weekly stats, flow benchmarks, and performance reporting
- Direct and develop designers, specialists, and contractors who execute the program
Requirements
- 6+ years in lifecycle, retention, CRM, or email and SMS marketing, with experience inside a brand or agency scaling eight- or nine-figure DTC brands where retention was owned as a meaningful share of revenue
- Deep, hands-on technical mastery of Klaviyo — flow architecture, triggers and conditions, opt-in and source tracking, suppressions, and deliverability — built and debugged independently
- You build, debug, and deploy flows and campaigns directly in Klaviyo — independently, without technical support
- Hands-on experience with Postscript or a comparable SMS platform at a lifecycle strategy level
- Proven, meaningful improvement to customer lifetime value in a durable goods or considered-purchase category
- Experience building complete flow coverage across a multi-product catalog and improving several funnels in parallel
- Genuine AI fluency as a builder — you have built AI-driven automations using tools like Claude, Make.com, N8N, or Zapier for tasks such as QA, segmentation, campaign generation, or reporting. This is not a nice-to-have; it is core to how this brand operates
- Sophisticated segmentation and data fluency — designs segmentation that compounds over time and reads performance data to drive decisions
- Strong editorial and cultural sensibility — holds a distinct brand voice and catches the nuance that elevates a program
- Experience directing specialists or contractors against a clear standard of output and quality
- Comfortable in a lean, fast-paced, founder-led startup environment where ownership is high and process is minimal
Nice to Have
- Experience in beauty, hair care, accessories, or apparel
- Track record building retention reporting or automation infrastructure from the ground up
- Experience scaling SMS into a material standalone revenue channel
- Experience supporting a brand through wholesale, retail, or international expansion
Ideal Candidate
This role is built for someone who is energized by owning a function outright. You anticipate gaps, close them early, bring solutions, and move the number. You are technically deep in Klaviyo and SMS, analytically fluent, and editorially sharp enough to hold a distinct brand voice at scale. You have already stood up retention programs at eight-figure brands and you know what good looks like — not just in metrics, but in the quality of the program. You bring AI into your workflow as a builder, not just a user. You thrive in lean, founder-led, fast-moving environments where ambiguity is normal, priorities shift quickly, and your work is visible from day one. If you need extensive process, handholding, or a structured corporate environment to do your best work, this is not the right role.