Headway.co logo

    Account Executive

    Headway.co

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

    ["Full-Time"]

    Work Type

    Remote

    Vertical

    SaaS

    Source

    jobicy

    About this role

    1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare.

    We've automated that.

    But we're going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI.

    We aren't just a billing layer; we are becoming the platform where care actually happens.

    We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

    As a Provider Growth Associate (Account Executive), you’ll have an instrumental impact as we expand Headway across the country. You’ll be directly responsible for scaling our community of therapists and psychiatrists in order to increase access to quality care for those who need it.

    As a sales expert in a rapidly scaling environment, you’ll be on the front line of expanding our therapist networks through a full-cycle sales motion. As the first point of contact for prospective providers, you’ll work cross-functionally to translate the insights you glean from your sales process into products and processes that help us execute on our mission.

    You'd love this role if:

    You have 1-3 years experience in consultative sales or consumer sales (bonus points if you’ve done this in a startup environment, or sold to small businesses before

    Selling Motion

    Prospecting

    Outbound-Heavy

    Self-sourced pipeline via cold outreach

    Buyer Persona

    C-Suite

    Selling to executive decision-makers

    Requirements at a Glance

    Experience·3+ years required
    Bachelor's Degree·Required

    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.

    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 Headway.co'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
    Research typical OTE splits for this role level and negotiate accordingly
    Prepare to discuss your home office setup and self-management discipline
    Review the job description and map your experience to each requirement
    Role Insights

    As an Account Executive with Headway.co, you'll own the entire revenue pipeline and be measured on quota attainment.

    Expect to work with recurring revenue models where customer retention is as important as acquisition.

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

    Are you a closer?

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