Job Description

*We are only considering candidates who currently live in or are willing to relocate to the Austin, TX Metro area to work from our office.*

About Outdoorsy Group

Outdoorsy Group is on a mission to restore our relationship with the outdoors. Our platform powers travel experiences through our RV rental marketplace, the Roamly insurance brand, and our growing portfolio of premium RV parks and resorts. Together, Outdoorsy and Roamly serve millions of outdoor travelers and vehicle owners, helping them explore the world with freedom and confidence.

About the Role

We are looking for an execution-focused Head of Product Operations to lead and scale product operations across Outdoorsy and Roamly. This is a high-impact leadership role responsible for creating operational leverage across the product development lifecycle—from roadmap planning to go-to-market execution and post-launch performance tracking.

What is Product Ops?

Operationalizing products means taking a product from concept or launch into a repeatable, scalable, and efficient operation—where it can grow, be supported, measured, and improved.

This is about turning product innovation into business results. 

As the connective tissue across Product, Engineering, Design, Data, Marketing, Sales, Customer Experience, and Insurance Operations, you will build the systems, processes, and rituals that allow our product teams to move faster, align better, and deliver at scale.

Requirements

What You’ll Do:

Product Operations

Go-to-Market (GTM) Playbooks: Create repeatable playbooks for launching and scaling products—internal enablement, customer messaging, metrics tracking.

Customer Onboarding Flows: Standardize how customers experience the product.

Cross-Sell and Upsell: Roamly and Outdoorsy Products through multiple touchpoints 

Support & Escalation Paths: Build FAQs, help center docs, and escalation policies early.

• Drive operational execution and excellence across the product development lifecycle.
• Build and manage cross-functional planning cadences (e.g., quarterly planning, sprint rituals, roadmap reviews).
• Drive product delivery velocity through streamlined tooling, workflows, and documentation.
• Identify and resolve process bottlenecks to help teams ship faster with higher quality.

Data, Measurement & Insights

• Partner with Data and Product teams to define, track, and report on product KPIs and OKRs.
• Own product performance dashboards and scorecards to drive insight-based decision-making.
• Establish feedback loops to capture Voice of the Customer, Support, and Sales to inform product prioritization.

Go-to-Market (GTM) Enablement

• Operationalize product launches across Outdoorsy and Roamly—ensuring cross-functional readiness, internal enablement, and clear success metrics.
• Work closely with Marketing, Insurance, and CX teams to coordinate timing, training, and communications.
• Create scalable playbooks for launching and iterating on product-led growth initiatives.

Strategic Planning & Alignment

• Support product and executive leadership with roadmap visibility, prioritization frameworks, and initiative tracking.
• Partner with Finance, RevOps, and Strategy teams to align product investments with business goals.
• Help facilitate annual and quarterly planning cycles with consistency and clarity.

Tools & Systems

• Own and optimize the product tech stack (e.g., Jira, Confluence, Productboard, Asana, etc.).
• Standardize documentation, intake processes, and product reporting workflows.

What You’ll Bring:

• 5+ years in Product Ops, Program Management, or similar operations roles in high-growth tech or product-led organizations.
• Proven track record of scaling product operations, leading cross-functional programs, and driving measurable impact.
• Deep understanding of product development best practices (Agile, OKRs, roadmapping, stakeholder comms).
• Exceptional communication and organizational skills—you can herd cats, align execs, and still stay in the weeds when needed.
• Strong analytical skills—you’re comfortable with dashboards, SQL, KPIs, and slicing product performance data.
• Bonus: Experience in marketplaces, insurtech, or dual-sided market platforms like Outdoorsy/Roamly.

Benefits

Why Outdoorsy Group?

• A chance to help shape the future of outdoor travel, mobility, and digital insurance.
• Join a profitable, mission-driven company with a clear growth path.
• Work alongside an entrepreneurial, passionate, and creative team that care deeply about the customer experience.
• Access to travel experiences, insurance innovation, and new tech at the intersection of leisure, lifestyle, and adventure.

Benefits & Perks:

• Opportunity to contribute to a high-growth, mission-driven company.
• Competitive salary and equity in one of the world’s fastest-growing companies.
• Comprehensive health and welfare benefits.
• 401(k) match to help secure your future.
• Flexible PTO to promote work-life balance.

Salary : $165,000 - $185,000/yr DOE

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