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    Mid-Market Account Executive

    Olo

    Remote
    Remote
    SaaS
    Hybrid
    See your match score
    Posted Today
    Work Type

    Remote

    Vertical

    SaaS

    Source

    jobscollider

    About this role

    Olo is a leading SaaS platform accelerating digital transformation in the restaurant industry, by helping customers deliver more personalized and profitable guest experiences. As a result, our digital ordering, payment, and guest engagement solutions enable brands to do more with less and make every guest feel like a regular.

    We are looking for a motivated Mid-Market Account Executive to add to our industry-leading GTM team. In this role, you will develop relationships with prospective brands ready to scale their digital potential.  The ideal candidate will possess technical aptitude, sharp project management skills, and comfort selling into all levels of an organization. Sound like you? Read on.

    Olo’s industry-leading online ordering platform has changed the restaurant landscape, helping many of our customers achieve 40%+ digital sales. You will be helping new logo brands move beyond fragmented tech by adopting an integrated platform for ordering, payments, and guest engagement.

    This is an exciting opportunity to join a growing group of Account Executives within Olo’s Mid-Market Sales team, focused on restaurant brands with between 5 and 49 locations. You will report to the Senior Manager, Mid-Market Sales, and can work remotely from anywhere in the U.S. or at Olo’s headquarters in NYC.

    How You’ll Make An Impact

    Own the full sales cycle — from self-sourced prospecting and territory prioritization through discovery, demo, proposal, and close. Build and manage a healthy pipeline through outbound prospecting, referrals, industry events, and partner channels. Drive awareness of Olo products and services to an assigned “Book of Business” and book meetings to explore sales opportunities.

    Deliver a unified vision of Olo’s Order, Pay, and Engage solutions, and present a recommended proposal for each prospect based on a thorough understanding of their business model, technology stack, and growth plans. Build and manage key stakeholders and “champions

    Commission Structure

    Base Salary

    Not disclosed — ask in interview

    Commission

    Structure not specified

    Ramp Period

    Not mentioned — clarify timeline

    Accelerators

    Yes

    Selling Motion

    Sales Cycle

    Mid-Market

    1–6 month cycles, moderate deal complexity

    Prospecting

    Channel / Partner

    Sell through partners, resellers, or alliances

    Buyer Persona

    Manager-Level

    Departmental buyers and team leads

    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 Olo'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

    Account Executives are the revenue engine of any sales organization — this role will require strong pipeline management and closing skills.

    Top SaaS reps often earn significant upside through accelerators once quota is exceeded.

    Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.

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