Regional Vice President of Sales, Providers

Freshpaint

. Lead, coach, and develop a team of seven Account Executives across SMB and MM/Small Enterprise segments .

Posted 11/7/2026full-timeRemote • United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in B2B sales leadership, with a strong focus on coaching and developing high-performing teams to achieve revenue targets. Proficient in executing repeatable sales strategies and managing complex sales processes within the healthcare sector.

Highest-signal resume keywords

B2B Sales LeadershipMEDDPICC MethodologyPipeline ManagementCoaching Account ExecutivesHealthcare Marketing Knowledge

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Quota AttainmentValue-Based SellingNegotiationsSales ForecastingComplex B2B SalesConsultative DiscoverySales Strategy DevelopmentMulti-ThreadingClosing ExperiencePerformance Improvement

Soft Skills

Strong CommunicationOrganizational SkillsLeadership SkillsAdaptabilityGrowth Mindset

Industry Keywords

Healthcare ProvidersDigital MarketingAdvertising TechnologyPatient AcquisitionData PrivacyHIPAA ComplianceMarketing-Focused SaaSSales PlaysCompetitive PositioningExecutive Engagement

About the role

Key responsibilities & impact

Lead, coach, and develop 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
Partner with Enablement and internal subject matter experts on onboarding and development
Set performance expectations, recognize top performers, address skill gaps, underperformance, and retention risks
Own new-business revenue targets and drive quota attainment
Maintain at least 3x qualified pipeline coverage and drive at least 40% sales-sourced pipeline generation
Build repeatable, segment-specific sales plays across healthcare provider segments
Participate in strategic opportunities through discovery, deal strategy, executive alignment, negotiations, and closing
Coach AEs through complex buying processes involving marketing leadership, executives, legal, procurement, security, and compliance
Maintain an opportunity open-to-closed-won win rate above 22%
Analyze lost deals, competitive dynamics, and buyer objections
Partner with Product and Product Marketing on competitive positioning, messaging, and sales effectiveness
Maintain an accurate weekly sales forecast and inspect pipeline health, stage progression, close dates, next steps, and forecast categories
Hold AEs accountable for accurate opportunity data and proactive risk identification
Partner with the VP of Sales during weekly forecast reviews
Develop scalable, segment-specific sales strategies for healthcare providers
Help AEs engage CMOs and senior marketing leaders with business cases tied to patient acquisition, marketing performance, digital advertising, and data privacy
Identify successful approaches, translate them into repeatable plays, and drive adoption across the team
Deliver $6–8 million in new-business ARR in FY2027 and expand Freshpaint’s healthcare provider market leadership

Requirements

What you’ll need

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
Deep understanding of complex B2B sales, including consultative discovery, value-based selling, executive engagement, multi-threading, negotiations, and closing
Demonstrated coaching ability and experience improving AE performance, developing talent, and building high-performing sales teams
Strong command of MEDDPICC and structured sales methodologies
Excellent pipeline management and forecasting skills
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
Strong communication, organizational, and leadership skills
High ownership, adaptability, and a growth mindset
Experience selling into Regional Health Systems, Multi-location Specialty Practices, DSOs, Urgent Care, or Health Tech organizations (nice to have)
Knowledge of healthcare marketing, patient acquisition, digital advertising, marketing technology, and healthcare provider buying landscape (nice to have)
Familiarity with HIPAA, data privacy, security reviews, and compliance-related challenges (nice to have)
Background leading a mix of SMB, Mid-Market, and Enterprise Account Executives (nice to have)
Must be located within the United States; Freshpaint only hires within the US

Benefits

Comp & perks

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