Regional Vice President of Sales, Providers

The posting, as Freshpaint wrote it

ABOUT FRESHPAINT

Healthcare is a $4+ trillion industry in the U.S. alone, and it’s undergoing a rapid digital transformation.

Hospitals, digital health companies, and life sciences organizations rely on analytics and advertising tools to reach patients, measure performance, and grow. But those tools weren’t built for regulated healthcare data. That creates real compliance risk and forces teams to choose between growth and privacy.

FRESHPAINT ELIMINATES THAT TRADE-OFF.

We’re a privacy-first data platform that helps healthcare organizations use modern marketing and analytics tools without exposing protected health information (PHI). Freshpaint sits between a company’s website or app and the third-party tools they use, automatically detecting and controlling sensitive data before it’s shared.

In short: we let healthcare teams move fast, safely.

BACKED BY TOP INVESTORS

Freshpaint is backed by some of the most respected names in technology, including:

• Y Combinator (OpenAI, Stripe, Airbnb, Coinbase, DoorDash)
• Intel Capital (Broadcom, Astera Labs, VMware, RedHat, MongoDB)

We’ve raised tens of millions of dollars in funding to build the privacy infrastructure layer for healthcare’s digital future.

What You'll Do

As the Regional Vice President of Sales, Providers at Freshpaint, you will lead, coach, and develop a team of seven Account Executives responsible for winning new business across Regional Health Systems, Multi-location Specialty Practices, Dental Service Organizations (DSOs), Urgent Care, and Health Tech organizations.

This is a hands-on sales leadership role for someone who knows how to win complex deals and make the people around them better. You will work directly with your AEs on customer calls, deal strategy, negotiations, and closing opportunities while building the coaching, accountability, and sales execution needed to consistently exceed revenue targets.

You will own your team's performance, pipeline health, forecast accuracy, and talent development, with responsibility for delivering $6-8 Million new-business ARR in FY2027. You'll report directly to the VP of Sales and play a critical role in expanding Freshpaint's market leadership across healthcare providers.

We're looking for a proven sales leader who combines deep industry knowledge with strong sales fundamentals, leads by example, and knows how to turn individual talent into consistent team performance.

Primary Responsibilities

Lead, Coach, and Develop a High-Performing Sales Team

• Lead a team of seven Account Executives, 2 SMB and 5 MM/Small Enterprise segments, driving consistent quota attainment and revenue growth.
• Conduct weekly 1:1s, deal reviews, call reviews, and team coaching sessions focused on improving selling skills, execution, and individual performance.
• Reinforce consistent application of MEDDPICC, Challenger, and value-based selling methodologies.
• Partner with Enablement and internal subject matter experts to accelerate

[…]
casting skills, including the ability to identify deal risks, assess opportunity quality, and communicate reliable revenue expectations.

• Proven ability to develop and execute repeatable sales strategies, generate pipeline, improve win rates, and drive consistent sales execution across multiple segments.
• Hands-on, player-coach leadership style, with the credibility and commercial judgment to join customer calls, influence deal outcomes, and help AEs close business.
• Strong communication, organizational, and leadership skills, with the ability to hold people accountable, deliver direct feedback, and build trust across teams.
• High ownership, adaptability, and a growth mindset, with the ability to execute effectively in a fast-growing environment where priorities, products, and processes continue to evolve.

Nice to Haves

• 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 that influence healthcare technology purchasing decisions.
• Background leading a mix of SMB, Mid-Market, and Enterprise Account Executives.

PERKS & BENEFITS

We take care of our team—here’s a peek at what you get when you join:

• Competitive pay + generous equity
• Half-day Fridays, every Friday
• 16 weeks fully paid parental leave (eligible after 6 months; commission-based roles receive 100% base salary during 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 (past trips: Arizona, Jackson Hole, Nashville, New Orleans & more)

And more! Check out our careers page https://www.freshpaint.io/careers for the full list.