Business Insurance Account Executive

    Gusto, Inc.

    🇺🇸 Remote
    Remote
    SaaS
    Hybrid
    See your match score
    Posted 1 week ago
    Work Type

    Remote

    Vertical

    SaaS

    Source

    weworkremotely

    About this role

    Headquarters: Atlanta, GA - Remote; Denver, CO - Hybrid; Phoenix, AZ - Remote

     


    About Gusto

    At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

     
    All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

     
    AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

    About the Role:

    We are seeking a highly motivated and licensed Property & Casualty (P&C) Insurance Broker to join our team as part of a critical pilot to launch a P&C broker model at Gusto. You will be essential in evolving Gusto's business insurance channel by acting as a licensed agent to quote and issue business insurance policies with our NEXT Insurance carrier partner. You will use your expertise to provide direct support and an improved experience for small business customers with complex insurance needs, helping to capture meaningfully higher revenue and ac

    Commission Structure

    Base Salary

    $,k

    Commission

    Structure not specified

    Ramp Period

    Not mentioned — clarify timeline

    Selling Motion

    Prospecting

    Channel / Partner

    Sell through partners, resellers, or alliances

    Requirements at a Glance

    Bachelor's Degree·Required

    Typical Day — Account Executive

    Stakeholder meetings3–5/week
    Executive presentations2–3/week
    Business cases & RFPs1–2/week
    Forecast & pipeline2×/week
    Champion coachingDaily

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

    Role Signals

    Green Flags

    ✓
    Equity/Stock Options

    Ownership stake offered

    ✓
    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

    remote
    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 Gusto, Inc.'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 Gusto, Inc. 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.

    Are you a closer?

    Interested in SaaS? Build your profile to get matched with roles like this.

    Explore More Sales Jobs

    Similar Roles

    Browse More Jobs

    Powered by LemClosers

    Ready to land your next closing role?

    Build your free closer profile to get matched with high-ticket sales opportunities, track applications, and showcase your track record.

    Join 500+ closers already on the platform • Free forever

    Get matched
    Create Free Profile