Head Of Sales - Remote Eligible

Head Of Sales

Sift Healthcare is seeking a Head of Sales to join our team. This is a foundational sales role, equal parts strategist, closer, and relationship builder. We're looking for a high-performing sales leader who thrives in ambiguity, knows how to sell to healthcare executives and is willing to work all parts of the sales cycle. You'll own the full sales funnel, architect our go-to-market strategy, close high-value deals, and lay the groundwork for future team growth. This role is ideal for someone who can move between boardrooms and cold outreach with credibility, resilience, and drive.

Sift is transforming healthcare payments by equipping healthcare organizations to fully leverage their payments data to work smarter, protect their margins and accelerate cash flow. Large health systems, leading HCIT vendors, payers and outsourced revenue management agencies use Sift's Payments Intelligence Platform, ML integrations and advanced analytics to optimize payment outcomes and enable data-driven decision-making within the revenue cycle.

Responsibilities

Sales Execution & Ownership

• Prospect and close early adopter clients
• Own the entire sales funnel from lead generation to signed contract
• Use a consultative sales approach to uncover deep pain and align Sift's value prop to customer goals
• Translate complex AI value props into business outcomes that resonate with buyers
• Close deals with hospital CFOs, revenue cycle execs, and strategic partners

Go-to-Market Strategy

• Define our initial commercial playbook: pricing, ICPs, messaging, outbound cadences
• Refine sales narratives based on market feedback and product evolution
• Partner with Marketing and Product to align outbound motion with positioning

Sales Infrastructure & AI-Driven Enablement

• Advance sales systems and workflows (CRM, reporting, pipeline reviews, AI tooling for outreach/tracking/insights)
• Stand up foundational sales systems and workflows, including CRM setup, pipeline reporting, and AI tools (i.e., Clay, Apollo, Lavender)
• Set clear goals and metrics to drive consistency and learning

Team Building & Leadership

• Serve as an individual contributor in the early stage by closing deals while laying groundwork for hiring
• Lay the foundation for a scalable sales team
• Hire and mentor early SDR/AE talent as revenue milestones are hit

Market Engagement

• Represent Sift at industry events, conferences, and partner forums
• Build and nurture relationships with high-value accounts and channel partners
• Feed insights back into product and commercial strategy

Qualifications

Required

• Own the entire sales funnel from lead generation to signed contract
• 7–10+ years in healthcare enterprise sales, including 3+ years in hospital RCM or finance
• Proven ability to sell into complex healthcare provider orgs (CFOs, VPs of Revenue Cycle, IT/Compliance)
• Experience closing 6- and 7-figure deals
• Strong grasp of denials, claims workflows, and reimbursement pain points
• Hands-on with outbound motion, CRM tools (HubSpot), and pipeline management
• Excellent communication, executive presence, and commercial instincts
• Bias toward ownership, action, and iteration

Preferred

• Experience at a health tech startup or AI-forward company
• Familiarity with denial analytics, predictive modeling, or revenue integrity workflows
• Pre-existing relationships with health systems or RCM vendors
• Exposure to channel/partnership sales motion

Compensation

Compensation will be based on skills, experience, and performance.

About Sift Healthcare

Sift is a data science company working to improve payments operations and outcomes in the healthcare industry. We are a growing and dynamic team that is serious about technology. Based in Milwaukee, Wisconsin, Sift is thriving and looking for motivated team members who will help shape our culture. Sift offers competitive salaries and benefits. Learn more about Sift at www.sifthealthcare.com.

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