Senior Manager of Retention Strategy, Outside
$80-110k
+ Bonus + Commission
Tableau
Hubspot
Amplitude
Senior level
Remote from US
Active lifestyle content hub
Open for applications
Active lifestyle content hub
501-1000 employees
B2CLifestyleContentDigital MediaSports
Open for applications
$80-110k
+ Bonus + Commission
Tableau
Hubspot
Amplitude
Senior level
Remote from US
501-1000 employees
B2CLifestyleContentDigital MediaSports
Company mission
To inspire and enable people to discover that life is best spent outside experiencing healthy, connected, and fulfilling lives.
Role
Who you are
- 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
What the job involves
- 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
- Within 1 Month, You Will:
- 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
- Within 3 Months, You Will:
- 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
- Within 6 Months, You Will:
- 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
- Within 12 Months, You Will:
- 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
Our take
Keeping people connected is among the many benefits of the digital world. Outside - formerly known as Pocket Outdoor Media - provides digital content for outdoor enthusiasts and athletes to find events, trade tips, and easily find the lifestyle content that is right for them.
Outside brings together a variety of traditional brands as well as additional content to create a complete user experience. Through its site, users can access meal plans, gear reviews or even online courses, as well as find the latest developments in any outdoor recreational or competitive activity.
The value of digital content is growing at an impressive rate, as is the target audience for Outdoor's content as the popularity of the outdoors is on the rise. As the market continues to grow, the company finds itself in a promising position for future growth, and it will be interesting to see what it focuses on next.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-5% employee growth in 12 months
Company
Funding (2 rounds)
Feb 2021
$150m
SERIES B
Jul 2020
$14m
SERIES A
Total funding: $164m
Company benefits
- Equity: we believe that all employees are owners and that we all contribute to the success of the company
- Comprehensive benefits package: Health, Dental, Vision, Life & AD&D, and more!
- Flexible time away: we believe in both the importance of working hard AND taking time to refresh and rejuvenate
- Learning & development: we put employees first and provide resources for personal and professional advancement
- Fringe benefits: cell phone reimbursement, fitness and ClassPass access, commuter program, etc
Company HQ
Goss - Grove, Boulder, CO
Leadership
Robin Thurston
(CEO)Former CEO of Helix and Pocket Outdoor Media. They also worked at Under Armour as an EVP and Chief Digital Officer.
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