Senior Retention Strategist

Headquarters: United States URL: http://lilosocial.com

About Lilo Social Lilo Social is a full-funnel eCommerce growth agency specializing in acquisition and retention for direct-to-consumer brands. With a team of over 65 professionals, we deliver best-in-class paid media, email marketing, and creative services to help brands scale profitably. We work across the entire customer lifecycle from content creation and paid advertising to conversion rate optimization and retention marketing. Our partnership-first approach has earned us a 90% client retention rate and recognition as an Inc. 5000 honoree for three consecutive years (2023, 2024, 2025). We are proud to be a Klaviyo Master Elite Agency, a distinction held by only 0.2% of Klaviyo's 6,500+ partners. To date, we have driven billions of dollars in attributed revenue for our partners. The Role As a Senior Retention Strategist, you will architect and execute comprehensive retention strategies that maximize customer lifetime value across the entire post-purchase journey. You will own the strategic vision for retention programs spanning email, SMS, subscription optimization, loyalty initiatives, and customer success transforming one-time buyers into high-value, loyal customers. This role combines strategic thinking with hands-on execution to drive measurable revenue growth and retention for our DTC ecommerce partners. What Success Looks Like Consistent month-over-month increases in customer LTV and retention revenue across your client portfolioMeasurable reduction in churn rates and improvement in repeat purchase frequency through strategic lifecycle programsData-driven segmentation strategies that deliver personalized customer experiences and drive engagement across all touchpointsStrong cross-functional collaboration that aligns retention initiatives with acquisition and creative strategies to optimize the full customer journey Responsibilities Develop and execute comprehensive lifecycle retention strategies encompassing email, SMS, subscription programs, loyalty initiatives, and customer success touchpointsDesign and architect advanced segmentation frameworks and customer journey maps that deliver personalized experiences across the entire post-purchase lifecycleBuild and optimize subscription retention programs including churn reduction strategies, failed payment recovery, dunning management, and upgrade/downgrade flowsLead strategic A/B testing roadmaps across all retention channels to continuously improve performance and identify scalable opportunitiesAnalyze customer cohorts, purchase patterns, and behavioral data to identify at-risk segments and develop targeted retention initiativesCreate advanced automation flows in Klaviyo including welcome series, abandoned cart recovery, post-purchase sequences, win-back campaigns, and VIP customer nurtureCollaborate with creative and design teams to develop high-converting retention creative assets and messaging frameworks that drive actionMonitor and report on retention KPIs including LTV, repeat purchase rate, churn rate, revenue per recipient, engagement metrics, and cohort analysisPresent strategic insights and performance results to client leadership teams with actionable recommendations for growthPartner cross-functionally with paid media, CRO, and creative teams to ensure cohesive customer experiences from acquisition through retentionMentor and develop retention team members, sharing best practices and elevating the team's strategic capabilitiesStay current on retention marketing trends, platform updates, subscription commerce best practices, and emerging technologies in the lifecycle marketing space Requirements 4+ years of experience in retention marketing, lifecycle marketing, or customer success with a focus on DTC ecommerce brandsExpert-level proficiency in Klaviyo with deep understanding of advanced segmentation, flow architecture, and analytics capabilitiesProven track record of driving significant revenue growth and LTV improvement through comprehensive retention programsStrong experience with subscription commerce including churn analysis, cohort retention optimization, and subscription lifecycle managementAdvanced analytical skills with ability to extract insights from complex datasets, build predictive models, and make data-driven strategic recommendationsDemonstrated client-facing experience presenting strategies, insights, and results to senior stakeholders with confidence and clarityDeep understanding of lifecycle marketing principles including customer journey mapping, segmentation strategy, and multi-touch attributionLeadership experience mentoring team members, developing retention frameworks, and building scalable processesExperience with subscription platforms such as Recharge, Skio, Ordergroove, or similar subscription management toolsProficiency with additional retention channels including direct mail, loyalty programs, referral systems, or community building initiatives Nice to Have Technical knowledge of API integrations, webhooks, and advanced Klaviyo custom properties or eventsExperience with analytics platforms such as Looker, Tableau, or advanced Shopify analytics for cohort and LTV analysisBackground in customer success, retention operations, or subscription analytics roles Compensation and Benefits Benefits: 401(k) Retirement Plan: Fully customizable 401(k) with up to 4% company matchComprehensive Health Coverage: Fully-covered medical, dental, and vision insuranceTime Off: Competitive PTO policy and paid holidays to maintain work-life balanceWellness Benefits: Complimentary Headspace subscription and fitness stipendFully Remote: Work from anywhere with flexible hours and a distributed team cultureTechnology Supplied: Equipped with the latest laptop and necessary tools for successProfessional Development: Opportunities for growth, training, and expanded responsibilitiesCompensation: Competitive salary commensurate with experience.

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