Regional Vice President of Sales, Providers

The role

You will lead, coach, and develop a team of seven Account Executives. You will drive new-business revenue targets and manage sales execution for healthcare providers.

What you will do

• Lead a team of seven Account Executives across SMB and MM/Small Enterprise segments.
• Conduct weekly 1:1s, deal reviews, call reviews, and team coaching sessions.
• Reinforce MEDDPICC, Challenger, and value-based selling methodologies.
• Own new-business revenue targets to deliver $6-8 Million new-business ARR in FY2027.
• Maintain at least 3x qualified pipeline coverage.
• Drive at least 40% sales-sourced pipeline generation through AEs and SDRs.
• Participate in strategic customer opportunities including discovery, negotiations, and closing.
• Maintain an opportunity open-to-closed-won win rate above 22%.
• Maintain a reliable, accurate, and up-to-date weekly sales forecast.
• Develop scalable, segment-specific sales strategies for healthcare providers.

Required qualifications

• Proven B2B sales leadership experience managing, coaching, and developing quota-carrying Account Executives.
• Direct, successful closing experience as an Account Executive.
• Strong experience selling to CMOs, senior marketing executives, and business decision-makers.
• Background in digital marketing, advertising technology, marketing agency services, or marketing-focused SaaS.
• Deep understanding of complex B2B sales, including consultative discovery, value-based selling, executive engagement, multi-threading, negotiations, and closing.
• Demonstrated coaching ability.
• Strong command of MEDDPICC and structured sales methodologies.
• Excellent pipeline management and forecasting skills.
• Proven ability to develop and execute repeatable sales strategies.
• Hands-on, player-coach leadership style.
• Strong communication, organizational, and leadership skills.

Nice to have

• Experience selling into Regional Health Systems, Multi-location Specialty Practices, DSOs, Urgent Care, or Health Tech organizations.
• Established knowledge of healthcare marketing, patient acquisition, digital advertising, marketing technology, and the healthcare provider buying landscape.
• Familiarity with HIPAA, data privacy, security reviews, and compliance-related challenges.
• Background leading a mix of SMB, Mid-Market, and Enterprise Account Executives.

Benefits

• Competitive pay + generous equity
• Half-day Fridays, every Friday
• 16 weeks fully paid parental leave
• Flexible PTO with a required 2-week minimum
• Top-tier health, dental & vision (100% covered for you, 80% for dependents)
• Intentional & engaging company offsites

About the company

Freshpaint is a privacy-first data platform that helps healthcare organizations use modern marketing and analytics tools without exposing protected health information (PHI). The company is backed by investors including Y Combinator and Intel Capital.