Job Description

About The Outdoorsy Group

The Outdoorsy Group is the global leader in outdoor travel and digital insurance for the specialty markets, dedicated to connecting people with memorable outdoor experiences and providing consumers and businesses with digital insurance products through it’s Roamly open API platform.

With a rapidly growing on demand marketplace for RVs and Campervans with offices in Austin, Toronto, Florida, California and the U.K. and an industry-leading digital insurance business, Roamly, we are redefining how people experience the outdoors.  Having achieved sustained profitability and surpassing $3 billion in transactions, we have ambitious plans to scale to $8 billion by 2029.

Role Overview

We are seeking an experienced Vice President of Finance to lead our financial team and function, planning, and execution as we continue to scale. This executive will play a critical role in driving financial performance, optimizing unit economics, and ensuring operational excellence across all business units, including our marketplace, insurance, and real estate initiatives. The VP of Finance will report directly to the CEO and will collaborate closely with the executive team to support strategic growth initiatives. 

This role will be based in Austin, Texas.

Requirements

Strategic Financial Leadership

• Develop and execute financial strategies aligned with The Outdoorsy Group’s long-term goals.
• Partner with leadership across Outdoorsy, Roamly, and the Outdoorsy Destination Network to drive sustainable growth.
• Identify and evaluate opportunities to enhance profitability, improve cash flow, and optimize capital allocation.

Financial Planning & Analysis (FP&A)

• Oversee budgeting, forecasting, and financial modeling to support strategic decision-making.
• Provide insights into key performance indicators (KPIs) to improve financial discipline and accountability.
• Support pricing and unit economics optimization across the company’s core revenue streams.

Capital Management & Corporate Development

• Assess capital allocation strategies, including potential debt and equity financing.
• Support M&A and partnership opportunities, including financial due diligence and integration planning.
  
  

Operational Finance & Risk Management

• Ensure financial controls, compliance, and risk management practices align with best-in-class standards.
• Oversee accounting, tax, and treasury functions to maintain financial health and regulatory compliance.
• Collaborate with Roamly’s finance team to support its insurance platform growth, profitability, and underwriting optimization.

Leadership & Cross-Functional Collaboration

• Lead and mentor a high-performing finance team.
• Partner with Product, Marketing, and Growth teams to evaluate business performance and investment opportunities.
• Support board and investor reporting, providing clear financial narratives and strategic recommendations.

Qualifications

• 10+ years of progressive finance leadership experience, ideally in high-growth marketplaces, insurance, fintech, or consumer tech businesses.
• Proven track record in financial strategy, FP&A, and capital allocation at a scaling company.
• Strong analytical mindset with deep experience in unit economics, cohort analysis, and financial modeling.
• Experience leading financial operations in multi-business environments (marketplace, insurance, fintech preferred).
• Deep understanding of risk management, compliance, and capital markets.
• Excellent communication skills with the ability to translate complex financial insights into actionable business strategies.
• Bachelor’s degree in Finance, Accounting, Economics, or a related field; MBA or CPA preferred.

Why Join The Outdoorsy Group?

• Be part of a category-defining company at the intersection of travel, tech, and insurance.
• Lead financial strategy for a company poised for exponential growth.
• Work alongside a passionate, entrepreneurial team dedicated to reshaping the outdoor experience.
• Competitive compensation, equity opportunities, and executive-level benefits.

Benefits

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: $210,000 - $240,000 DOE