Senior Manager, Retention Strategy

We’re looking for an experienced retention marketer to build and operationalize the retention and engagement function for Outside’s mapping and fitness portfolio — Gaia GPS, Trailforks, and the MapMy suite (MapMyRun, MapMyRide, MapMyWalk, MapMyFitness).

This role’s core mission is to preserve and grow recurring subscription revenue and increase customer lifetime value (CLTV) through strategic lifecycle, engagement, and retention programs.

You’ll define how we engage, educate, and retain subscribers across app and web platforms — transforming behavioral insights into activation and renewal strategies that deepen user loyalty and reduce churn.

While your primary focus (≈75%) will be on mapping and fitness apps— you’ll also partner with Media and Editorial growth leaders (≈25%) to share retention frameworks, insights, and playbooks that can be adapted across Outside’s broader subscription ecosystem.

This is a high-impact, strategic individual contributor role supported by shared creative, brand, and analytics resources. You’ll collaborate across Growth, Product, Brand, and BI to build scalable systems that sustain revenue growth and engagement for hundreds of thousands of outdoor enthusiasts worldwide.

• Define and own a data- and PLG-led retention roadmap for Gaia GPS, Trailforks, and MapMy apps, focusing on activation, engagement, renewal, and re-engagement.
• Develop a clear strategy for improving CLTV through lifecycle communications, feature adoption, and user education.
• Partner with Media Growth and Editorial leaders to apply best practices from mapping retention programs — ensuring alignment across the broader ecosystem.
• Collaborate with Growth, Product, Brand, and BI to ensure retention efforts are prioritized, measurable, and connected to company OKRs.

• Audit and optimize subscriber lifecycle touchpoints across email, in-app messaging, social, and paid re-engagement channels.
• Partner with email and creative teams to deploy onboarding, renewal, and winback campaigns with measurable goals.
• Develop and test passive churn prevention tactics (billing retries, reminders) and active churn interventions (exit offers, feedback loops, reactivation campaigns).

• Partner with Product Managers and the Brand Director to plan and execute feature launch and education campaigns that drive engagement and retention.
• Develop lifecycle and messaging plans that showcase new value to existing subscribers and encourage product adoption.
• Measure post-launch engagement impact and identify ongoing opportunities for education and upsell.

• Collaborate with Brand and Community Managers to amplify retention initiatives across owned social, community forums, and ambassador programs.
• Identify opportunities for user-generated content, challenges, and seasonal re-engagement campaigns that foster community participation and loyalty.

• Define and monitor retention KPIs: active days, renewal rate, churn, feature adoption, and LTV.
• Partner with Finance, BI and Growth to build dashboards and generate insights for continuous optimization.
• Design and implement an experimentation framework to test lifecycle messaging, sequencing, and engagement offers.

• Partner with creative, brand, and email specialists for execution.
• Collaborate with Product on retention-driving features and PLG experiments.
• Coordinate with Customer Support to identify churn drivers and inform save strategies.
• Align with Performance Marketing on paid re-engagement and winback campaigns.

• Complete onboarding across Growth, Product, Brand, and BI to understand the mapping and fitness ecosystem.
• Audit current retention touchpoints (email, in-app, social, paid re-engagement) and identify quick wins.
• Deliver a Retention Baseline Report summarizing key metrics, pain points, and early hypotheses.

• Deliver a Retention & Engagement Roadmap aligned with product and growth OKRs.
• Launch 1–2 quick-win initiatives (e.g., onboarding improvements, reactivation flows).
• Establish a retention reporting cadence with BI for churn, engagement, and renewal metrics.

• Execute 3–5 multi-channel retention initiatives across email, in-app, and organic channels.
• Co-lead a feature GTM campaign with Product and Brand to drive adoption and retention.
• Formalize a repeatable campaign development process and testing framework.

• Demonstrate measurable improvement in renewal and engagement rates for Gaia GPS, Trailforks and MapMyFitness (MVP)
• Deliver an Annual Retention Impact Report summarizing results, ROI, and CLTV improvements.
• Build and present a 2026 Retention Expansion Plan, including headcount recommendations, experimentation roadmap, and forecasted impact.

• 5–8 years in retention or lifecycle marketing role, ideally in a subscription or app-based business.
• Demonstrated ability to increase retention and engagement through data-driven initiatives.
• Understanding of app engagement metrics and community-driven growth loops.
• Experience querying structured data (e.g., SQL) or using analytical tools (Looker, Amplitude, Snowflake) to inform retention and engagement strategy.
• Hands-on experience with HubSpot, OneSignal or  equivalent CRM tools.
• Excellent cross-functional communicator who can bridge creative, product, and data disciplines.
• Passion for outdoor adventure, fitness, and technology that connects people to the outdoors.

• Retention roadmap implemented and measured against growth OKRs.
• Established baselines and reporting cadence for CLTV, churn, and engagement.
• Measurable improvement in renewal and active engagement rates.
• Proven ability to scale insights and frameworks across the  broader subscription ecosystem.
• Business case approved for expanding the retention function in FY26.

Outside is building a connected ecosystem that inspires millions to explore the outdoors. This role gives you the chance to shape how users engage with some of the world’s leading mapping and fitness apps and outdoor brands,  and to turn insights into lasting loyalty.

You’ll join a collaborative, data-informed, and mission-driven team that values curiosity, impact, and a shared love for adventure.

What We Offer:

Entirely remote jobs that could be performed in Colorado: Employees can expect to be paid a salary of  between $80,000 to $110,000.  Additional compensation may include a bonus or commission . Additional benefits include health care, vision, dental, retirement, Flexible Time Away,  sick leave, and more.  This salary range is merely an estimate and may vary based on an applicant’s location, market data/ranges, an applicant’s skills and prior relevant experience, certain degrees and certifications, and other relevant factors.