Braun Board

Lead Sales Executive and Account Manager - Roamly UK

The Ride Platform · London, UK

Base
Not disclosed
OTE
Not disclosed
Quota attainment
Not disclosed
Posted
1mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon The Ride Platform's careers page

The job

What you'd do
Find and win new UK customers among medium and large companies that run vehicle fleets, plus rental businesses, then look after them once they sign. You'll also sell more to existing clients as their fleets grow.
Who you'd sell to
Still reading the posting. Check back within the hour.
Where deals come from
Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay
No pay listed at all.
Transparency
Shares 1 of 5: quota, attainment, deal size, territory, sales cycle.
Time on market
Open 33 days. Normal, but not fresh.
Company hiring
This is their only open sales role.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

  1. 1.

    What percentage of fully ramped reps hit quota last year?

    OTE is what you could earn. This is how likely you are to earn it.

  2. 2.

    What percentage of reps on the team have been here more than 18 months?

    Tenure shows whether people stay long enough to get paid.

  3. 3.

    Has the comp plan changed in the last 12 to 18 months? What changed?

    A plan that changes every year means the goalposts keep moving.

  4. 4.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  5. 5.

    What are the base and the OTE for this role?

    No point investing hours before you know the number.

  6. 6.

    Why is this role open? Did someone leave, or is it new?

    New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

  1. 1.

    Can I see the full comp plan in writing, including clawbacks and accelerators?

    What's in writing is what gets paid. Read it before you sign.

  2. 2.

    Can I see the actual comp distribution for the team last year, not just the OTE?

    The spread shows what most reps really take home. OTE is just the target.

  3. 3.

    I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?

    Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

Got an offer from The Ride Platform? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
+ Add offer details (optional)

Goes straight to my inbox. I never share it with employers or recruiters.

Full posting
About Roamly Roamly is a premier InsurTech platform built specifically for the mobility and commercial fleet economy. Our pioneering insurance solutions—including our commercial Protection Experience (Roamly PX)—offer embedded risk management and dynamic commercial coverage built for rental operators, platforms, and fleet managers. To power complete end-to-end fleet operations, our product suite also includes Wheelbase, the leading fleet management software ("the operating system") for vehicle, campervan, RV, and mobility operators. As we continue our rapid global growth, we are expanding directly into the UK market. We are looking for a high-energy, commercially minded pioneer to spearhead this effort, establishing Roamly’s footprint and delivering our combined insurance and software product suite to UK operators. Role Overview As a Senior Sales Executive and Account Manager, you will serve as the primary driver of our UK market launch. This is a dynamic hybrid role combining full sales cycle execution (hunting new business) with ongoing account servicing and retention (farming existing accounts). You will focus on introducing Roamly PX to UK fleet operators and rental businesses, while also leveraging Wheelbase SaaS as an integrated or standalone software solution to give UK clients a seamless operational suite. Requirements 1. UK Market Spearhead & Sales Generation - Drive UK Expansion: Act as the primary on-the-ground sales owner for Roamly in the UK, building initial market momentum, brand presence, and localized sales pipelines. - Full Sales Cycle Ownership: Prospect, pitch, run live product demos, negotiate, and close mid-to-large UK fleet operators, peer-to-peer rental businesses, and commercial fleets. - Sell the Full Ecosystem: Articulate the combined value proposition of Roamly PX (commercial risk and policy management) alongside Wheelbase SaaS (fleet optimization, booking engines, and logistics management). - Consultative Selling: Analyze UK operator models, evaluate current insurance vulnerabilities/gaps (e.g., downtime, off-rent exposures), and demonstrate cost savings and risk reduction using Roamly and Wheelbase. 2. Account Servicing & Relationship Management - Account Servicing: Serve as the dedicated account manager for UK clients post-sale, handling day-to-day policy maintenance, fleet additions/deletions (endorsements), billing inquiries, and software support. - Onboarding & Adoption: Partner with Underwriting and Implementation teams to ensure UK operators are seamlessly onboarded, fully compliant, and maximizing software usage. - Account Retention & Expansion: Build strong, long-term relationships with fleet owners to maximize lifetime account value (LTV), cross-selling additional Wheelbase modules, and scaling policy coverage as client fleets grow. - Market Feedback Loop: Act as the voice of the UK market internally—providing vital localized feedback to Product, Underwriting, and Executive leadership to refine our UK go-to-market strategy. Qualifications & Requirements - UK B2B Commercial Sales Experience: 2+ years in B2B sales or account management within the UK commercial insurance, InsurTech, fleet management, mobility, or SaaS sectors. - UK Insurance Knowledge: Strong understanding of UK commercial motor insurance, fleet risk, or Property & Casualty (P&C) fundamentals. Relevant UK insurance qualifications (e.g., CII / Cert CII) are strongly preferred. - Full-Lifecycle Capability: Proven ability to both prospect and close new deals (Hunter) while delivering exceptional ongoing account management and servicing (Farmer). - SaaS & Tech Aptitude: Experience presenting and selling software solutions (SaaS), with the ability to comfortably demonstrate the Wheelbase platform alongside Roamly insurance products. - Self-Starter / Entrepreneurial Mindset: Comfortable operating as an early-stage market spearhead—possessing the drive to create structure, navigate ambiguity, and establish a new regional territory. - CRM & Tools: Proficient in modern sales and account management platforms (e.g. Close.io, Tableau,etc). Key Competencies - Commercial Drive & Hustle: Motivated by launching a top-tier product into a new market and achieving aggressive revenue growth targets. - Relationship Builder: High emotional intelligence, capable of earning the trust of small business owners and C-suite fleet executives alike. - Adaptability & Resilience: Comfortable working across time zones with global tech/underwriting hubs while maintaining deep responsiveness to local UK clients. Benefits What We Offer - Competitive Base Salary + Uncapped Variable OTE (Commissions and bonuses tied to UK market growth, close rates, and account retention). - UK Benefits Package: Pension contributions, health coverage options, and flexible time off. - Global Career Opportunity: Be the foundational sales hire in a major new geographic market for a high-growth scale-up.
Apply →