Head of Sales - Remote

Overview

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.

In Short

• 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
• Define our initial commercial playbook: pricing, ICPs, messaging, outbound cadences
• Advance sales systems and workflows (CRM, reporting, pipeline reviews, AI tooling)
• Serve as an individual contributor while laying groundwork for hiring
• Represent Sift at industry events and build relationships with accounts
• Feed insights back into product and commercial strategy

Requirements

• 7–10+ years in healthcare enterprise sales, including 3+ years in hospital RCM or finance
• Proven ability to sell into complex healthcare provider orgs
• Experience closing 6- and 7-figure deals
• Strong grasp of denials, claims workflows, and reimbursement pain points
• Hands-on with outbound motion, CRM tools, and pipeline management
• Excellent communication and commercial instincts
• Bias toward ownership, action, and iteration

Benefits

• Competitive salaries and benefits
• Opportunity to shape company culture
• Dynamic team environment
• Work in a growing data science company