Roamly & Wheelbase - SMB/MM Account Executive

Job Description

Job Description

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.

At Roamly and Wheelbase Pro , we are redefining mobility, fleet management, and insurance for the modern world. Wheelbase is the premier fleet management SaaS ("the operating system") for auto rental, carshare, RV, and mobility fleets. Deeply embedded into our software is Roamly—a pioneering InsurTech platform providing proprietary, real-time commercial insurance that protects fleets during downtime, active rentals, and rideshare periods.

Together, we eliminate operational friction and help fleet owners scale from simple asset owners to high-performing commercial operators.

About the Role

We are seeking a high-velocity, commercially minded Account Executive to drive the adoption of our dual-threat platform. In this role, you will own the full B2B sales cycle. You aren't just selling software features; you are presenting a transformative business model. You will consultatively demonstrate how Wheelbase Pro optimizes utilization and revenue, while Roamly solves their largest operational headache: cost-effective, seamless risk management.

Requirements

Key Responsibilities & Deliverables

• Own the Full Sales Cycle: Prospect, build, and manage a high-velocity pipeline targeting mid-to-large fleet operators, carshare businesses, RV rental companies, and modern mobility services.
• Deliver the Dual Value Proposition: Execute impactful, consultative demonstrations that seamlessly tie the operational power of Wheelbase SaaS (booking, analytics, dispatch) to the financial security of embedded Roamly insurance.
• Navigate Complex B2B Sales: Confidently pitch to multiple stakeholders, including Operations Managers, CFOs, and C-Suite executives, translating technical SaaS perks and insurance cost-reductions into ROI.
• Uncover Risk Pain Points: Analyze an operator's current insurance gaps (e.g., personal lines exclusions, downtime vulnerabilities, rideshare Period 0 gaps) and position Roamly as the total compliance solution.
• Collaborate on Onboarding: Partner closely with our internal Underwriting, Customer Success, and Implementation teams to ensure smooth transition from closed-won to active utilization and policy binding.
• Maintain CRM Hygiene: Keep pristine records of sales activities, notes, and accurate forecasting metrics within our CRM.

Who You Are

Required Qualifications:

• Proven SaaS Sales Track Record: 2–4+ years of B2B SaaS account executive experience, preferably in a fast-paced environment with a high deal velocity.
• The "Hunter" Mentality: Deep mastery of outbound prospecting, cold outreach, and building your own pipeline rather than just waiting for marketing inbound leads.
• Comfort with Complexity: Ability to learn and confidently articulate complex insurance concepts, regulatory guidelines, and multi-location software logic.
• Adaptable & Resilient: A startup mindset—thriving in a dynamic, rapidly expanding market where you help write the sales playbook rather than just reading it.

Nice-to-Haves:

• An active Property & Casualty (P&C) Insurance License (or a strong willingness to obtain one quickly with company support).
• FinTech, InsurTech, or Fleet Familiarity: Experience or a strong working knowledge in commercial insurance, InsurTech, automotive telematics, mobility-tech, or fleet management logistics
• An existing network within the commercial vehicle rental, carsharing host networks, or dealership fleet space.

Benefits

Compensation & Benefits:

• Competitive Compensation & Uncapped Commissions: On Target Earnings (OTE) of $150-$250K.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off.
• Fun Office Atmosphere: Lively office, stocked with endless snacks, regular Happy Hours, catered lunches, and team building events.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.
• Schedule: This is a full-time hybrid position.