Roamly & Wheelbase - SMB/MM Account Executive

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

• 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

• 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