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 75 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 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

Responsibilities

- 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

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 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

Nice to Have

- 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 Perks

- 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.

📌 Senior Retention Strategist (Canada)
🏢 Lilo Social
📍 Canada