Account Executive – SaaS, Embedded Insurance

Outdoorsy

Account Executive responsible for driving B2B SaaS sales in Fleet Management and InsurTech. Engaging mid-to-large fleet operators and presenting a dual-threat platform.

Posted 6/11/2026full-timeSan Francisco • California • 🇺🇸 United StatesJuniorMid-Level💰 $75,000 per yearWebsite

About the role

Key responsibilities & impact

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 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.

Requirements

What you’ll need

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.
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

Comp & perks

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.

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

B2B SaaS salesoutbound prospectingcold outreachpipeline managementconsultative sellingCRM managementsales forecastinginsurance compliance analysisdemonstration executionROI translation

Soft Skills

adaptabilityresiliencecommunicationcollaborationstakeholder engagementproblem-solvinganalytical thinkingconsultative approachnegotiationnetworking

Certifications

Property & Casualty Insurance License