Senior Retention Strategist

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.

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.

• Consistent month-over-month increases in customer LTV and retention revenue across your client portfolio
• Measurable reduction in churn rates and improvement in repeat purchase frequency through strategic lifecycle programs
• Data-driven segmentation strategies that deliver personalized customer experiences and drive engagement across all touchpoints
• Strong cross-functional collaboration that aligns retention initiatives with acquisition and creative strategies to optimize the full customer journey

• Develop and execute comprehensive lifecycle retention strategies encompassing email, SMS, subscription programs, loyalty initiatives, and customer success touchpoints
• Design and architect advanced segmentation frameworks and customer journey maps that deliver personalized experiences across the entire post-purchase lifecycle
• Build and optimize subscription retention programs including churn reduction strategies, failed payment recovery, dunning management, and upgrade/downgrade flows
• Lead strategic A/B testing roadmaps across all retention channels to continuously improve performance and identify scalable opportunities
• Analyze customer cohorts, purchase patterns, and behavioral data to identify at-risk segments and develop targeted retention initiatives
• Create advanced automation flows in Klaviyo including welcome series, abandoned cart recovery, post-purchase sequences, win-back campaigns, and VIP customer nurture
• Collaborate with creative and design teams to develop high-converting retention creative assets and messaging frameworks that drive action
• Monitor and report on retention KPIs including LTV, repeat purchase rate, churn rate, revenue per recipient, engagement metrics, and cohort analysis
• Present strategic insights and performance results to client leadership teams with actionable recommendations for growth
• Partner cross-functionally with paid media, CRO, and creative teams to ensure cohesive customer experiences from acquisition through retention
• Mentor and develop retention team members, sharing best practices and elevating the team's strategic capabilities
• Stay current on retention marketing trends, platform updates, subscription commerce best practices, and emerging technologies in the lifecycle marketing space

• 4+ years of experience in retention marketing, lifecycle marketing, or customer success with a focus on DTC ecommerce brands
• Expert-level proficiency in Klaviyo with deep understanding of advanced segmentation, flow architecture, and analytics capabilities
• Proven track record of driving significant revenue growth and LTV improvement through comprehensive retention programs
• Strong experience with subscription commerce including churn analysis, cohort retention optimization, and subscription lifecycle management
• Advanced analytical skills with ability to extract insights from complex datasets, build predictive models, and make data-driven strategic recommendations
• Demonstrated client-facing experience presenting strategies, insights, and results to senior stakeholders with confidence and clarity
• Deep understanding of lifecycle marketing principles including customer journey mapping, segmentation strategy, and multi-touch attribution
• Leadership experience mentoring team members, developing retention frameworks, and building scalable processes
• Experience with subscription platforms such as Recharge, Skio, Ordergroove, or similar subscription management tools
• Proficiency with additional retention channels including direct mail, loyalty programs, referral systems, or community building initiatives

• Technical knowledge of API integrations, webhooks, and advanced Klaviyo custom properties or events
• Experience with analytics platforms such as Looker, Tableau, or advanced Shopify analytics for cohort and LTV analysis
• Background in customer success, retention operations, or subscription analytics roles

Benefits:

• 401(k) Retirement Plan: Fully customizable 401(k) with up to 4% company match
• Comprehensive Health Coverage: Fully-covered medical, dental, and vision insurance
• Time Off: Competitive PTO policy and paid holidays to maintain work-life balance
• Wellness Benefits: Complimentary Headspace subscription and fitness stipend
• Fully Remote: Work from anywhere with flexible hours and a distributed team culture
• Technology Supplied: Equipped with the latest laptop and necessary tools for success
• Professional Development: Opportunities for growth, training, and expanded responsibilities
• Compensation: Competitive salary commensurate with experience.