Fleetio logo

    Account Executive, Mid-Market

    Fleetio

    🇺🇸 USA
    Remote
    ["Full-Time"]
    SaaS
    Hybrid
    See your match score
    Posted Today
    Job Type

    ["Full-Time"]

    Work Type

    Remote

    Vertical

    SaaS

    Source

    jobicy

    About this role

    A little

    about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company.

    Fleetio is also a proud founding member of the Rails Foundation!

    More about our team and company:

    Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg Our careers page: https://www.fleetio.com/careers

    Do you have a passion for sales and a desire to join a fast-growing and profitable software company? Are you an overachiever who wants a high-earning potential that’s based on performance? Are you well-versed in prospecting and closing? If so, you might be our next Mid-Market Account Executive.

    In this role, you'll work with a mix of inbound and outbound leads and close new customers using sales tactics (emails, phone calls, web-based demos, etc.)

    Who you are You’re a driven, results-oriented sales professional who thrives in a fast-paced environment and is motivated by uncapped earning potential. You’re excited by the opportunity to work with fascinating customers and prospects across a wide range of industries—because nearly every organization that operates a fleet is a potential Fleetio customer.

    You’ll be responsible for sourcing and closing new business, influencing and owning the sales process while driving meaningful outcomes and ARR growth. You know how to leverage cross-functional teams to convert high-impact prospects into long-term customers, and you’re eager to join a team of “A” players who are passionate, supportive, and committed to success.

    Whether you’re working remotely from anywhere in the U.S. or from our HQ in Birmingham, AL, you’ll find a collaborative, customer-centric culture where your contributions matter and your success is celebrated. Your impact

    Know our

    Selling Motion

    Sales Cycle

    Mid-Market

    1–6 month cycles, moderate deal complexity

    Prospecting

    Hybrid

    Mix of inbound leads and outbound prospecting

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Requirements at a Glance

    Bachelor's Degree·Required
    Prospecting·Required skill

    Typical Day — Account Executive

    Demos & presentations4–6/week
    Prospecting calls20–30/day
    Proposal writing2–3/week
    Pipeline review2×/week

    Estimates based on role type and selling motion — actual may vary by company.

    Role Signals

    Green Flags

    ✓
    Remote Friendly

    Location flexibility

    SaaS — Interview Intel

    Typical Sales Cycle

    30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)

    Common Buyer Objections

    • "We're locked into a contract with [competitor]"
    • "We built something in-house already"
    • "We don't have budget until next quarter"
    • "Our team won't adopt another tool"

    Key Industry Metrics

    ARR / MRRNet Revenue Retention (NRR)CAC Payback PeriodLogo Churn vs Revenue ChurnACV (Avg Contract Value)Magic Number

    Hot Topics to Reference

    • • AI-native product disruption
    • • PLG vs sales-led motion debate
    • • Vertical SaaS consolidation
    • • Usage-based pricing models

    Use these insights to speak the buyer's language in interviews.

    Tags

    sales
    —

    Walk me through your discovery process.

    Template question
    —

    How do you handle a prospect who goes silent mid-deal?

    Template question
    —

    Tell me about your largest closed deal and the sales cycle.

    Template question
    —

    How do you build business cases for stakeholders?

    Template question
    —

    Describe a deal you lost and what you learned.

    Template question
    Research Fleetio's product, recent news, and key competitors
    Prepare metrics: quota attainment %, average deal size, win rate
    Practice a 2-minute product demo pitch for a mock discovery call
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    This Account Executive position at Fleetio involves managing the full sales cycle from prospecting through close.

    SaaS sales roles typically involve consultative selling with longer deal cycles.

    This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.

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