SMB/MM Account Executive

Role Overview

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, presenting a transformative business model to mid-to-large fleet operators, carshare businesses, RV rental companies, and modern mobility services.

What You Will Do

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.

Why It Might Be a Fit

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.

Requirements

• Proven SaaS Sales Track Record: 2–4+ years of B2B SaaS account executive experience
• The “Hunter” Mentality: Deep mastery of outbound prospecting, cold outreach, and building your own pipeline
• 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

Benefits

• Competitive Compensation & Uncapped Commissions
• 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