Lead Sales Executive and Account Manager
About the job
- At least 2 years of B2B sales or account management experience in the UK commercial insurance, InsurTech, fleet management, mobility, or SaaS sectors.
- Strong understanding of UK commercial motor insurance, fleet risk, or Property & Casualty fundamentals.
- Ability to prospect and close new deals while managing and servicing ongoing accounts.
- Experience presenting and selling SaaS solutions, including demonstrating the Wheelbase platform alongside insurance products.
- Comfort operating as an early-stage market spearhead, creating structure, navigating ambiguity, and establishing a new regional territory.
- Proficiency with modern sales and account management platforms such as Close.io and Tableau.
- Ability to work across time zones with global technology and underwriting teams while remaining responsive to UK clients.
- Drive Roamly's UK expansion as the primary on-the-ground sales owner, building market momentum, brand presence, and localized sales pipelines.
- Own the full sales cycle by prospecting, pitching, running live product demonstrations, negotiating, and closing mid-to-large UK fleet operators, peer-to-peer rental businesses, and commercial fleets.
- Sell Roamly PX alongside Wheelbase SaaS, articulating the combined value of insurance, fleet optimization, booking engines, and logistics management.
- Analyze UK operator models and insurance vulnerabilities, including downtime and off-rent exposures, and demonstrate potential cost savings and risk reduction using Roamly and Wheelbase.
- Serve as dedicated account manager for UK clients after the sale, handling policy maintenance, fleet additions and deletions, endorsements, billing inquiries, and software support.
- Partner with Underwriting and Implementation teams to onboard UK operators, support compliance, and maximize software usage.
- Retain and expand accounts by building long-term relationships, cross-selling Wheelbase modules, and scaling policy coverage as client fleets grow.
- Provide localized UK market feedback to Product, Underwriting, and Executive leadership to refine the UK go-to-market strategy.
- Relevant UK insurance qualifications, such as CII or Cert CII, are strongly preferred.
About the company
The Ride Platform provides an integrated mobility ecosystem for vehicle rental operators, combining marketplaces, software, and insurance. Its marketplaces connect owners and renters through Outdoorsy for RVs and Ride for professional car fleets, while Wheelbase is a SaaS operating system that helps fleet operators manage pricing and utilization. Roamly is an AI-first insurance provider with Lloyd’s Coverholder status, offering real-time, risk-adjusted coverage for standard policies and autonomous or FSD-enabled operation. The goal is to help mobility entrepreneurs turn any vehicle into a business at scale, using an end-to-end Operator Economy and AI-enabled tools to drive growth.
Company Size
201-500
Company Stage
N/A
Total Funding
N/A
Headquarters
Austin, Texas
Founded
2015
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Simplify's Take
What believers are saying
- Roamly’s July 29, 2026 London expansion opens UK and European fleet insurance sales.
- Jeff Cavins said on June 17, 2026 that Roamly FSD is live and cuts costs 50%.
- The Ride Platform’s four billion dollars in processed transactions proves real operator demand and scale.
What critics are saying
- Roamly’s FSD pricing on June 17, 2026 ties underwriting to unproven autonomous claims data.
- The company still depends on vehicle utilization; a downturn in bookings crushes marketplace, SaaS, and insurance.
- Any Lloyd’s or regulatory setback would cripple Roamly and break the platform’s cross-sell engine.
What makes The Ride Platform unique
- June 2026 rebrand to The Ride Platform unifies Outdoorsy, Ride, Wheelbase, and Roamly.
- Roamly’s July 29, 2026 London hub and Lloyd’s Coverholder status strengthen insurance differentiation.
- Ride targets professional fleets with operator economics, not consumer marketplace extraction, since 2026.
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Benefits
- Health Insurance
- 401(k) Company Match
- Unlimited Paid Time Off
- Company Equity