About the RoleWe 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.
RequirementsKey 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 AreRequired 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.
BenefitsCompensation & 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.
