Senior Retention Strategist

Lilo Social; United States; Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

Fully Remote

401(k) with match

Health insurance

Paid holidays

Headspace subscription

Fitness stipend

Laptop provided

Professional development

Job summary

Lilo Social is a full-funnel eCommerce growth agency. We seek a Senior Retention Strategist to own retention programs across email, SMS, loyalty, and customer success for our DTC partners.

You will design lifecycle strategies, lead segmentation, and drive revenue growth while coordinating with acquisition and creative teams. Remote-first, 401(k) and comprehensive benefits are offered.

Qualifications

• 5+ years of retention marketing, lifecycle marketing, or customer success for DTC brands.
• Expert Klaviyo proficiency with advanced segmentation and flows.
• Proven revenue/LTV growth from retention programs.
• Experience with subscription platforms and churn analysis.
• Strong analytical, data-driven decision making.
• Client-facing experience with senior stakeholders.
• Knowledge of lifecycle marketing concepts and multi-touch attribution.
• Leadership and mentoring experience.
• Experience with Looker/Tableau analytics.

Responsibilities

• Develop and execute lifecycle retention strategies across email, SMS, subscriptions, loyalty, and customer success touchpoints.
• Design segmentation frameworks and journey maps for post-purchase retention.
• Build and optimize subscription retention programs including churn reduction and dunning.
• Lead A/B testing roadmaps across retention channels to improve performance.
• Analyze cohorts and purchase patterns to identify at-risk segments.
• Create Klaviyo automation flows (welcome, abandoned cart, post-purchase, VIP).
• Collaborate with creative and paid media to align retention with acquisition.
• Monitor retention KPIs and report insights to leadership.
• Mentor retention team members and share best practices.
• Stay current on retention trends and platform updates.

Skills

Retention marketing

Lifecycle marketing

Customer success

Analytics

Leadership

Subscription analytics

Tools

Klaviyo

Recharge

Skio

Ordergroove

Looker

Tableau

Job description

Lilo Social is a full-funnel eCommerce growth agency specializing in acquisition and retention for direct-to-consumer brands. With a team of over 80 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 design and run retention strategies that grow customer lifetime value across the full post-purchase journey. You will own the strategic vision for retention programs across email, SMS, subscription optimization, loyalty, and customer success, turning one-time buyers into loyal, high-value customers. The role combines strategy 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 portfolio
• Measurable reduction in churn and higher 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 work with acquisition and creative strategy across the full customer journey

Responsibilities

• Develop and execute lifecycle retention strategies across email, SMS, subscription programs, loyalty initiatives, and customer success touchpoints
• Design advanced segmentation frameworks and customer journey maps that deliver personalized experiences across the post-purchase lifecycle
• Build and optimize subscription retention programs, including churn reduction, failed payment recovery, dunning management, and upgrade/downgrade flows
• Lead A/B testing roadmaps across all retention channels to improve performance and find scalable opportunities
• Analyze customer cohorts, purchase patterns, and behavioral data to identify at-risk segments and build targeted retention initiatives
• Build advanced automation flows in Klaviyo, including welcome series, abandoned cart recovery, post-purchase sequences, win-back campaigns, and VIP nurture
• Work with creative and design teams to develop high-converting retention creative and messaging frameworks
• 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 with clear, actionable recommendations
• Partner with paid media, CRO, and creative teams to keep the customer experience consistent from acquisition through retention
• Mentor and develop retention team members, sharing best practices and raising the team's strategic capabilities
• Stay current on retention marketing trends, platform updates, subscription commerce best practices, and new lifecycle marketing technology

Requirements

• 5+ years of experience in retention marketing, lifecycle marketing, or customer success with a focus on DTC eCommerce brands
• Expert-level proficiency in Klaviyo, with a deep understanding of advanced segmentation, flow architecture, and analytics
• Proven track record of driving significant revenue growth and LTV improvement through retention programs
• Strong experience with subscription commerce, including churn analysis, cohort retention optimization, and subscription lifecycle management
• Advanced analytical skills, with the ability to pull insights from complex datasets, build predictive models, and make data-driven recommendations
• 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 tools

Nice to Have

• Experience with additional retention channels, including direct mail, loyalty programs, referral systems, or community building
• 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

Compensation and Benefits

• Compensation: Competitive salary commensurate with experience. Salary ranges vary by location.
• 401(k) Retirement Plan: Fully customizable 401(k) with up to 4% company match
• Comprehensive Health Coverage: Fully-covered medical, dental, and vision insurance
• Generous 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