Regional Vice President of Sales, Providers at Freshpaint

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 onboarding, ramp time, and ongoing development.
• Set clear performance expectations, recognize top performers, and proactively address skill gaps, underperformance, and retention risks.
• Build a culture of accountability, collaboration, continuous improvement, and high performance.
• Drive Revenue Growth and Pipeline Generation
• Own the team's new-business revenue targets, driving toward 100% quota attainment while maintaining a minimum average attainment of 85% across total team quota capacity.
• Maintain at least 3x qualified pipeline coverage to support consistent revenue generation and predictable growth.
• Drive at least 40% sales-sourced pipeline generation through Account Executives and their aligned SDRs.
• Build and execute repeatable, segment-specific sales plays across Regional Health Systems, Specialty Practices, DSOs, Urgent Care, and Health Tech.
• Monitor pipeline creation, conversion, and coverage, proactively addressing gaps before they impact revenue performance.
• Lead Strategic Deals and Improve Win Rates
• Actively participate in strategic customer opportunities, providing hands-on support with discovery, deal strategy, executive alignment, negotiations, and closing.
• Coach AEs to navigate complex buying processes involving marketing leadership, executive stakeholders, legal, procurement, security, and compliance.
• Maintain an opportunity open-to-closed-won win rate above 22%, continuously identifying opportunities to improve conversion.
• Analyze lost deals, competitive dynamics, and buyer objections to identify recurring challenges and implement improvements.
• Partner with Product and Product Marketing to strengthen competitive positioning, customer messaging, and sales effectiveness.
• Know when to step directly into a deal and when to coach an AE to lead independently.
• Own Forecast Accuracy and Sales Execution
• Maintain a reliable, accurate, and up-to-date weekly sales forecast, with clear visibility into expected results, opportunities, and risks.
• Inspect pipeline health, stage progression, close dates, next steps, and forecast categories to ensure deal quality and realistic expectations.
• Hold AEs accountable for maintaining accurate opportunity data, documenting next steps, and proactively identifying deal risks.
• Partner with the VP of Sales during weekly forecast reviews, clearly communicating expected performance, risks, and action plans.
• Build and Execute Repeatable Sales Strategies
• Develop scalable, segment-specific sales strategies that reflect the unique business needs, buying processes, and competitive dynamics of healthcare providers.
• Help AEs engage CMOs and senior marketing leaders with compelling business cases tied to patient acquisition, marketing performance, digital advertising, and data privacy.
• Identify successful sales approaches, translate them into repeatable plays, and drive consistent adoption across the team.
• Adapt strategies as Freshpaint expands its product capabilities, customer segments, and market opportunities.

Desired Skills and Experience

• Proven B2B sales leadership experience managing, coaching, and developing quota-carrying Account Executives, with a demonstrated record of achieving or exceeding team revenue targets.
• Direct, successful closing experience as an Account Executive, with a track record of meeting or exceeding quota and independently navigating complex sales opportunities.
• Strong experience selling to CMOs, senior marketing executives, and business decision-makers, preferably within healthcare providers or similarly complex organizations.
• 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 understanding of complex B2B sales, including consultative discovery, value-based selling, executive engagement, multi-threading, negotiations, and closing.
• Demonstrated coaching ability, with specific examples of improving AE performance, developing talent, and building high-performing sales teams.
• Strong command of MEDDPICC and structured sales methodologies, with the ability to reinforce consistent qualification and execution across an entire team.
• Excellent pipeline management and forecasting 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.