Outdoorsy is the world’s most trusted, high quality RV travel and accommodations marketplace that includes our owned and operated destinations. 

Born from a desire to reconnect with nature and others, Outdoorsy was founded on a mission to use technology to provide access to outdoor travel and entrepreneurial opportunities to RV owners in a sustainable way, increasing the usefulness of under utilized mobility assets.  

Since 2015, we’ve given our guests more than 10 million nights outdoors. We operate globally in 14 countries, with North America as our strategic focus.

Outdoorsy is part of the The Ride Platform, which operates a unique ecosystem of marketplace solutions, specialty insurance, and fleet software purpose-built for the next generation of mobility entrepreneurs.




Outdoorsy

About Us


The Ride Platform, Inc. is the parent company of Outdoorsy, Ride, Wheelbase, and Roamly. We're named for the thing every part of our business runs on: the ride — the single transaction where an operator meets a renter. We're the only company building end-to-end for the Operator Economy: the marketplaces to book (Outdoorsy, Ride), the enterprise SaaS to manage (Wheelbase), and the insurtech (Roamly) to protect the assets people turn into profitable businesses. We enable millions of people to explore the world, while helping independent operators build generational wealth. Our mission is to build the essential infrastructure for the mobility economy.

About Roamly


Roamly is a leading provider of specialty insurance for the modern mobility and marketplace travel economy. As a Lloyd's Coverholder and AI-first insurance innovator, we combine deep carrier partnerships with proprietary technology to help consumers, professional fleet owners, and marketplaces unlock new revenue while managing risk. Our platform uses AI, automation, and embedded distribution to deliver tailored coverage for RVs, carsharing, and other emerging mobility models — spanning underwriting, claims, compliance, analytics, and real-time risk management.

Learn more at www.roamly.com.

About The Role

We're looking for a hands-on accounting professional who naturally takes ownership and thrives on problem-solving. This role calls for strong technical accounting knowledge, meaningful insurance industry experience, and the confidence to independently manage complex accounting matters — from digging into the underlying data and researching the right accounting treatment, to bringing the right people together and driving a solution through to completion.

Requirements

Key Responsibilities & Deliverables

Insurance Accounting

Oversee monthly premiums, claims, settlements, and internal and external reporting for all insurance productsOwn assigned insurance-side areas from beginning to end, ensuring accurate and timely financial reportingProvide accounting leadership and subject matter expertise for insurance-related operations, including revenue, premiums, commissions, claims, reserves, carrier or partner activity, and related balance sheet accounts


Close, Reporting Technical Accounting

Play an active role in the monthly, quarterly, and annual close processes, including journal entries, reconciliations, accruals, and financial resultsAnalyze complex or unusual transactions and determine the appropriate accounting treatment with limited supervisionReview financial results and account activity to identify inconsistencies, trends, errors, and areas requiring further investigationTake ownership of accounting issues by researching the underlying problem, recommending solutions, and driving matters through resolutionAssist with international accounting activities, including foreign subsidiaries, intercompany transactions, foreign currency matters, and local reporting requirements, as applicableAssist with external audits and provide requested documentation, schedules, and accounting support


Leadership & Process Improvement

Partner with senior management on technical accounting matters, financial reporting, process improvements, and special projectsProvide guidance, review, and mentorship to other accounting team members while helping develop stronger accounting fundamentals and analytical skills across the teamImprove accounting processes and controls by challenging existing practices and identifying opportunities for greater accuracy, efficiency, scalability, and automationHelp document accounting policies, procedures, and internal controls as the organization continues to grow and evolveServe as a dependable accounting leader who can step into new or ambiguous areas, establish structure, and move work forward


Special Projects & Cross-Functional Work

Lead and execute special projects as needed, including researching issues, developing solutions, and driving projects through completionCollaborate cross-functionally with finance, operations, compliance, tax, treasury, and other business teams to understand transactions and ensure appropriate accounting treatment

Who You Are

Required Qualifications

Bachelor's degree in Accounting, Finance, or related fieldStrong knowledge of GAAP and fundamental accounting principlesMinimum of 5 years of progressive accounting experience, specifically within the insurance or reinsurance sectorExperience managing complex accounting processes with a high degree of independenceDemonstrated ability to research accounting issues, exercise sound judgment, and independently determine appropriate next stepsStrong analytical and problem-solving skills with the ability to understand both transaction-level details and the broader financial impactAbility to work effectively in an evolving environment where processes or responsibilities may not always be clearly definedStrong communication skills and the ability to work effectively with both accounting professionals and non-accounting business partners


Preferred Qualifications

CPA preferredExperience with international accounting, foreign subsidiaries, multi-currency environments, and/or intercompany accountingExperience working within a complex multi-entity organizationExperience with accounting systems & close/reconciliation platforms (e.g., NetSuite, Applied Epic, Numeric, Floqast)Experience identifying and implementing accounting process improvements or automationPrevious experience mentoring, reviewing, or developing junior accounting staff


Benefits

Compensation & Benefits:

Competitive Compensation: Base salary of $130,000 - $140,000 DOEGrowth Opportunity: Join a company in its early stages and help build its foundation for successEquity: Opportunity to earn equity compensationComprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time OffWork-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure

Senior Accounting Manager, Insurance

What the job involves