Retention Director, Outside
Growth Marketing
$110-140k
+ Bonus + Commission
Active lifestyle content hub
Be an early applicant
Active lifestyle content hub
501-1000 employees
Be an early applicant
$110-140k
+ Bonus + Commission
501-1000 employees
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
- The ideal candidate is an experienced retention marketer who is deeply curious about customer motivations, can swiftly drive action from high-level strategy to detailed execution, and excels at making the business case for new initiatives to drive growth
- 7–10+ years of experience in retention or lifecycle marketing—ideally in a subscription or app-based business
- Proven track record of reducing churn, increasing LTV, and scaling post-purchase engagement strategies across complex ecosystems
- Deep expertise in subscription retention mechanics, especially passive churn mitigation tactics (e.g., dunning, billing retries, payment lifecycle optimization)
- Hands-on experience working with lifecycle platforms (Hubspot or similar), analytics tools (Amplitude, Tableau, or similar), and subscription management platforms (Stripe, Piano, or similar)
- Strong analytical mindset with comfort owning subscriber lifecycle metrics, forecasting, and experimentation frameworks
- Exceptional cross-functional communicator and collaborator with experience influencing Product, Engineering, Finance, and Customer Support teams
- Passion for the outdoors, wellness, and building products that inspire people to lead active, healthy lives is a plus
What the job involves
- We’re looking for a customer-obsessed, data-centric Retention Director to join our growth marketing team at Outside
- You will lead efforts to engage and retain subscribers across Outside’s mapping app and media subscription products*
- From ownership of retention-focused pricing strategy to personalized subscriber engagement loops and churn mitigation strategies, you’ll be responsible for building and powering an end-to-end retention engine to maximize renewing revenue and increase LTV
- You’ll become a champion for subscriber wants and needs, unearthing insights to inform how and where we connect with them to drive engagement with our products and reinforce the value of what they’re paying for
- Close cross-functional collaboration is essential to be successful in this role
- Build, manage, and execute a strategic roadmap for subscriber retention and revenue growth
- Own retention-focused pricing strategy, including renewal pricing models, retention and upgrade offers, winback discounts, and testing frameworks that balance subscriber value and revenue growth
- Lead the optimization of the entire post-purchase lifecycle in collaboration with the vertical Growth Marketing owners, with coordinated and personalized messaging designed to educate subscribers about our products and their benefits, drive engagement and feature discovery, and deliver long-term retention
- Manage all passive churn mitigation strategies and tactics, including dunning, credit card retries, and stop-save programs
- Develop and test active churn mitigation campaigns, winback journeys, and segmentation strategies across email, push, and in-product surfaces
- Lead initiatives to uncover subscriber behaviors, preferences, and friction points—translating these insights into preemptive churn interventions that boost long-term value (e.g., onboarding, seasonal usage spikes, behavioral triggers)
- Own ongoing cross-platform subscriber communication to drive engagement and satisfaction, including updates about changes to subscriber benefits
- Partner with Customer Service to define, evaluate, and optimize retention-focused policies related to inquiries about subscription offerings and requests for cancelation, refunds, disputes, etc
- Collaborate closely with Product leadership and acquisition-focused Growth Marketing peers to shape and grow overall subscription offering, including the evolution of bundling and benefits to include high-value features that drive acquisition and retention as well as overall pricing strategy for both domestic and international markets
- Own reporting for subscriber health metrics (retention, LTV, churn, engagement), including partnering with Business Intelligence to develop relevant dashboard and regularly sharing performance with senior leadership and cross-functional stakeholders
- Create and nurture a culture focused on testing, analytics, creativity, and customer affinity, influencing teams across Product, Marketing, Business Intelligence, and Engineering
- Implement and oversee rigorous testing methodologies on creative, channels, and retention campaigns to maximize ROI and scale successful initiatives
- Present retention strategies, results, and forecasts to senior leaders
- Stay abreast of industry trends, emerging technologies, and best practices in retention marketing, incorporating innovative approaches into the company's growth strategy
- Join an ambitious and nimble Growth Marketing team focused on full-funnel strategies to drive subscription growth
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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