Senior Retention Strategy Manager

Subscription Insider; Andover (MA); On-site; USD 160,000 - 175,000; Full time

Benefits offered by this job

Employee Stock Purchase Plan

401K with Company Match

Medical, Dental & Vision Insurance

Paid Parental Leave

9 Paid Company Holidays

Flexible Time Off (With Manager Approval)

Job summary

Subscription Insider is seeking a Senior Retention Strategy Manager in Andover, Massachusetts. This role focuses on developing strategies to enhance customer engagement and retention, utilizing data analysis to identify trends and implement reactivation tactics. Ideal candidates should have over 10 years of experience in marketing or customer engagement roles and strong analytical capabilities. The position includes competitive compensation and a variety of employee benefits, including stock options and a 401K plan.

Qualifications

• 10+ years of experience in retention, lifecycle strategy, or customer engagement roles.
• Demonstrated ability to build and launch initiatives that improve engagement and retention.
• Ability to analyze behavioral trends to identify drivers of churn.

Responsibilities

• Develop retention strategy frameworks to enhance customer loyalty.
• Partner with CRM and lifecycle teams to implement prioritized programs.
• Analyze trends and develop strategies for reactivation of lapsed customers.

Skills

Retention strategy development

Analytical skills

Cross-functional collaboration

Customer engagement

Behavioral segmentation

Job description

About The Role

The Senior Retention Strategy Manager will help shape and advance The RealReal’s long‑term approach to customer engagement and lifetime value growth. This role focuses on defining the strategic frameworks, cross‑channel priorities, and cross‑functional initiatives that deepen engagement, reduce churn, and drive repeat behavior across the member lifecycle.

Working in close partnership with Lifecycle/CRM, Product, Analytics, Merchandising, Creative, and Sales, this role translates customer insight into actionable programs that influence behavior and unlock measurable business impact. This is a strategic, hands‑on role for an operator who thrives on connecting dots across teams and turning ideas into scalable solutions.

What You Get To Do Every Day

Retention & Engagement Strategy

• Develop and evolve retention strategy frameworks that clarify how we drive engagement, repeat purchase, and long‑term loyalty.
• Define the role of lifecycle channels including email, push, SMS, in‑app messaging, and emerging touchpoints within a cohesive engagement model.
• Partner closely with CRM and Lifecycle teams to translate strategy into prioritized programs and journeys.

Cross‑Functional Solutions to Drive LTV

• Identify opportunities to improve frequency, reactivation, and churn reduction through cross‑functional initiatives spanning marketing, product, merchandising, and sales.
• Lead strategic initiatives from insight through launch, aligning stakeholders and ensuring measurable outcomes.
• Shape onboarding, habit‑forming experiences, and high‑value feature adoption strategies.
• Drive engagement and new features in app to drive further adoption and stickiness.
• Manage test and learns across all platforms in partnership with CRM team.

Churn Reduction & Reactivation

• Analyze behavioral and cohort trends to identify key drivers of churn and disengagement.
• Develop and prioritize scalable reactivation strategies for lapsed buyers and consignors.
• Build business cases and test plans for new retention levers.

Measurement & Experimentation

• Define KPIs and success metrics that quantify retention impact and inform roadmap prioritization.
• Champion a structured test‑and‑learn agenda in partnership with Analytics and Lifecycle teams.
• Synthesize learnings into clear recommendations and scalable playbooks.

Strategic Alignment & Communication

• Create clear briefs and strategy documents that guide cross‑functional partners.
• Present insights and recommendations to senior stakeholders.
• Ensure retention strategy is embedded in broader growth and product roadmaps.

Minimum Requirements

• 10+ years of experience in retention, lifecycle strategy, growth marketing, or customer engagement roles in e‑commerce, marketplace, or digital‑first businesses.
• Demonstrated ability to build and launch initiatives that improve engagement, retention, or LTV.
• Strong analytical orientation with fluency in cohort analysis, experimentation, and behavioral segmentation.
• Experience working cross‑functionally with CRM, Product, and Analytics teams.
• Ability to influence without direct authority and drive alignment across multiple stakeholders.
• A bias toward action and comfort operating in a fast‑paced, evolving environment.

Compensation, Benefits, + Perks

• Employee Stock Purchase Plan
• 401K with Company Match
• Medical, Dental & Vision Insurance
• Paid Parental Leave
• 9 Paid Company Holidays
• Flexible Time Off (With Manager Approval)

The expected salary range for this role is $160,000.00-$175,000.00. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR’s total rewards package. Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.

Equal Employment Opportunity

The RealReal is committed to providing an equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or Veteran status. We will consider qualified applicants for a position regardless of arrest or conviction records. At TRR, People Come First. That’s why diversity and inclusion are vital to our priorities as an equal opportunity employer.

Physical Demands / Accommodations

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.