• Location: Milwaukee, Wisconsin
  • Remote: Remote
  • Type: Direct Hire
  • Job #5607

Carex is partnering with a healthtech startup industry partner to hire a Head of Sales. This is a foundational sales leadership role for a high-performing, entrepreneurial individual ready to own the full commercial motion of an early-stage company. Equal parts strategist, closer, and relationship builder, the Head of Sales will drive initial revenue growth while laying the groundwork for a scalable sales function. The ideal candidate will be an expert in selling into healthcare provider organizations, with experience closing 6- and 7-figure deals and a deep understanding of hospital revenue cycle operations. If you thrive in ambiguity, can move seamlessly between boardroom conversations and cold outreach, and want to shape go-to-market strategy from the ground up, this is the role for you.

What You’ll Do

  • Sales Execution & Ownership

  • Prospect and close early adopter clients

  • Own the entire sales funnel—from lead generation through signed contracts

  • Use a consultative approach to uncover pain points and align solutions to client goals

  • Communicate complex AI and data solutions in terms of clear business outcomes

  • Close deals with hospital CFOs, revenue cycle executives, and strategic partners

  • Go-to-Market Strategy

  • Define the commercial playbook including pricing, ICPs, messaging, and outbound cadences

  • Refine sales narratives based on market feedback and product development

  • Align sales efforts with Marketing and Product to ensure consistency and impact

  • Sales Infrastructure & Enablement

  • Build and optimize foundational sales systems including CRM, reporting, and AI sales tooling

  • Set KPIs and establish processes for pipeline visibility, tracking, and iteration

  • Utilize tools such as HubSpot, Clay, Apollo, and Lavender to drive outreach and insight

  • Team Building & Leadership

  • Operate as a hands-on individual contributor while establishing a repeatable sales process

  • Develop the hiring plan for future SDR/AE talent aligned with revenue milestones

  • Mentor and onboard new team members as the team scales

  • Market Engagement

  • Represent the company at key industry events, conferences, and partner forums

  • Develop strategic relationships with high-value accounts and channel partners

  • Share market insights with internal stakeholders to guide product and commercial strategy

    What You’ll Bring

    • 7–10+ years in healthcare enterprise sales, with 3+ years in hospital RCM or finance

    • Proven ability to sell into complex provider organizations at the CFO and VP level

    • Demonstrated success closing high-value deals (6- and 7-figure contracts)

    • Strong knowledge of denials, claims workflows, and reimbursement challenges

    • Hands-on experience managing outbound efforts, CRMs, and pipeline strategy

    • Executive presence, persuasive communication skills, and commercial acuity

    • High ownership mindset with a bias toward action and experimentation

    Preferred:

    • Experience at a health tech startup or AI/data-focused company

    • Familiarity with denial analytics, predictive modeling, or revenue integrity workflows

    • Pre-existing provider or vendor relationships

    • Exposure to channel and partnership sales

    Compensation

    • Base Salary: $175,000–$200,000

    • Commission: Uncapped

    If the range doesn’t align with your needs, please still apply! Carex values transparency in all steps of the recruiting process. The range listed above is dependent on skills and experience as it relates to the role. New roles arise every day, and we want you to be the first to know when the right role pops up for you.

    Carex Consulting Group is an equal opportunity employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, marital status, disability, gender identity, or Veteran status.

    #LI-AS1
    #LI-Remote

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