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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, consultingatively demonstrating how Wheelbase Pro optimizes utilization and revenue, while Roamly solves their largest operational headache: cost-effective, seamless risk management.
Responsibilities
- Own the full sales cycle, including prospecting, pipeline building, and management for mid-to-large fleet operators, carshare businesses, RV rental companies, and modern mobility services.
- Execute consultative demonstrations linking the operational capabilities of Wheelbase SaaS with the financial security of Roamly insurance.
- Pitch to multiple stakeholders, including Operations Managers, CFOs, and C-Suite executives, translating technical benefits and cost reductions into ROI.
- Analyze operator insurance gaps and position Roamly as a comprehensive compliance solution.
- Collaborate with internal Underwriting, Customer Success, and Implementation teams for a smooth client transition.
- Maintain CRM hygiene with accurate sales activity records and forecasting.
Requirements
- Proven SaaS sales track record with 2-4+ years of B2B account executive experience, preferably in a fast-paced, high-deal-velocity environment.
- Demonstrated "hunter" mentality with mastery of outbound prospecting and cold outreach.
- Ability to learn and articulate complex insurance concepts, regulatory guidelines, and multi-location software logic.
- Adaptable and resilient with a startup mindset, comfortable contributing to the sales playbook in a dynamic market.
- An active Property & Casualty (P&C) Insurance License is a plus, or a strong willingness to obtain one.
- Experience or strong working knowledge in FinTech, InsurTech, automotive telematics, mobility-tech, or fleet management logistics is a plus.
- An existing network within the commercial vehicle rental, carsharing host networks, or dealership fleet space is a plus.
Skills
- B2B SaaS Sales
- Account Executive
- Outbound Prospecting
- Cold Outreach
- Pipeline Management
- Consultative Selling
- CRM Management
- Financial Analysis
- Risk Management
- Insurance Concepts
- Fleet Management
- SaaS Demonstration
Location
- Hybrid
Work Type
- Full-time
- Hybrid
Experience Level
- 2-4+ years B2B SaaS Account Executive experience
Salary/Compensations
- On Target Earnings (OTE) of $150-$250K
Benefits
- Competitive Compensation & Uncapped Commissions
- Growth Opportunity
- Equity compensation
- Full health and welfare benefits package
- 401(k) match
- Flexible Paid Time Off
- Fun office atmosphere with snacks, Happy Hours, catered lunches, and team building events
- RV rental discounts
About the Company
- The Ride Platform, Inc. is the parent company of Outdoorsy, Ride, Wheelbase, and Roamly, building end-to-end solutions for the Operator Economy in marketplaces, SaaS, and InsurTech.
- Wheelbase is a premier fleet management SaaS platform, and Roamly is a pioneering InsurTech platform providing proprietary, real-time commercial insurance.
- Together, they eliminate operational friction and help fleet owners scale their businesses.