Regional Vice President of Sales, Providers

Freshpaint

5d • $340,000 - $400,000

About The Position

Freshpaint is a privacy-first data platform that helps healthcare organizations use modern marketing and analytics tools while controlling sensitive data and protecting protected health information. The Regional Vice President of Sales, Providers will lead, coach, and develop a team of seven Account Executives selling to 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 involving direct support for customer calls, deal strategy, negotiations, and closing, alongside responsibility for coaching, accountability, and sales execution. The role owns team performance, pipeline health, forecast accuracy, talent development, and delivery of $6–8 million in new-business ARR in FY2027. It reports directly to the VP of Sales and contributes to expanding Freshpaint’s position in the healthcare provider market.

Requirements

• Proven B2B sales leadership experience managing, coaching, and developing quota-carrying Account Executives, with a record of achieving or exceeding team revenue targets.
• Direct, successful Account Executive closing experience, including a record of meeting or exceeding quota and independently navigating complex sales opportunities.
• Strong experience selling to CMOs, senior marketing executives, and business decision-makers; healthcare provider experience or experience with similarly complex organizations is preferred.
• Background in digital marketing, advertising technology, marketing agency services, or marketing-focused SaaS, with an understanding of how organizations evaluate marketing investments and measure business outcomes.
• Deep knowledge of complex B2B sales, including consultative discovery, value-based selling, executive engagement, multi-threading, negotiation, and closing.
• Demonstrated ability to improve Account Executive performance, develop talent, and build high-performing sales teams.
• Strong command of MEDDPICC and structured sales methodologies, with the ability to reinforce consistent qualification and execution across a team.
• Strong pipeline management and forecasting skills, including assessing opportunity quality, identifying deal risks, and communicating reliable revenue expectations.
• Ability to develop and execute repeatable sales strategies, generate pipeline, improve win rates, and drive consistent execution across multiple segments.
• Hands-on player-coach leadership style and the credibility and commercial judgment to join customer calls, influence deal outcomes, and help Account Executives close business.
• Strong communication, organizational, and leadership skills, including 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 work effectively in a fast-growing environment where priorities, products, and processes evolve.

Nice To Haves

• Experience selling into Regional Health Systems, Multi-location Specialty Practices, DSOs, Urgent Care, or Health Tech organizations.
• 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 in healthcare technology purchasing.
• Experience leading a mix of SMB, Mid-Market, and Enterprise Account Executives.

Responsibilities

• Lead and develop a team of seven Account Executives across SMB and Mid-Market/Small Enterprise segments.
• Conduct weekly one-on-ones, deal reviews, call reviews, and coaching sessions.
• Reinforce MEDDPICC, Challenger, and value-based selling methodologies.
• Partner with Enablement and subject matter experts to improve onboarding, ramp time, and ongoing development.
• Set performance expectations, recognize strong performance, address skill gaps and underperformance, and manage retention risks.
• Build a culture of accountability, collaboration, continuous improvement, and high performance.
• Own team new-business revenue targets, aiming for 100% quota attainment and at least 85% average attainment across total team quota capacity.
• Maintain at least 3x qualified pipeline coverage and drive at least 40% sales-sourced pipeline generation through Account Executives and aligned SDRs.
• Develop and execute repeatable sales plays for Regional Health Systems, Specialty Practices, DSOs, Urgent Care, and Health Tech.
• Monitor pipeline creation, conversion, and coverage, addressing gaps proactively.
• Participate directly in strategic opportunities, supporting discovery, deal strategy, executive alignment, negotiations, and closing.
• Coach Account Executives through complex buying processes involving marketing leaders, executives, legal, procurement, security, and compliance.
• Maintain an opportunity open-to-closed-won win rate above 22%, analyze lost deals and competitive dynamics, and implement improvements.
• Partner with Product and Product Marketing to improve competitive positioning, customer messaging, and sales effectiveness.
• Maintain a reliable, accurate weekly forecast and inspect pipeline health, stage progression, close dates, next steps, and forecast categories.
• Hold Account Executives accountable for accurate opportunity data, documented next steps, and proactive identification of deal risks.
• Partner with the VP of Sales in weekly forecast reviews, communicating expected performance, risks, and action plans.
• Develop scalable, segment-specific strategies that reflect provider business needs, buying processes, and competitive dynamics.
• Help Account Executives build business cases for CMOs and senior marketing leaders tied to patient acquisition, marketing performance, digital advertising, and data privacy.
• Identify successful approaches and turn them into repeatable sales plays adopted across the team.
• Adapt strategies as Freshpaint expands its product capabilities, customer segments, and market opportunities.

Benefits

• Competitive pay and generous equity.
• Half-day Fridays every Friday.
• 16 weeks of fully paid parental leave, eligible after six months; commission-based roles receive 100% of base salary during leave.
• Flexible PTO with a required two-week minimum.
• Health, dental, and vision coverage: 100% covered for the employee and 80% for dependents.
• Company offsites.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed