Regional Vice President of Sales, Providers

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead, mentor, and cultivate a team of seven Account Executives across the SMB and MM/Small Enterprise segments.

• Conduct weekly one-on-one meetings, deal assessments, call evaluations, and team coaching sessions.

• Reinforce MEDDPICC, Challenger, and value-based selling techniques.

• Collaborate with Enablement and internal subject matter experts for onboarding and professional development.

• Establish performance objectives, acknowledge top performers, address skill gaps, underperformance, and retention challenges.

• Take ownership of new business revenue targets and drive quota achievement.

• Maintain a minimum of 3x qualified pipeline coverage and aim for at least 40% sales-sourced pipeline creation.

• Develop repeatable, segment-specific sales strategies for healthcare provider segments.

• Engage in strategic opportunities through discovery, deal strategy, executive alignment, negotiations, and closing.

• Guide AEs through intricate buying processes involving marketing leadership, executives, legal, procurement, security, and compliance.

• Ensure an opportunity open-to-closed-won win rate above 22%.

• Analyze lost deals, competitive dynamics, and buyer objections.

• Collaborate with Product and Product Marketing on competitive positioning, messaging, and sales effectiveness.

• Maintain an accurate weekly sales forecast while monitoring 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 discussions.

• Develop scalable, segment-specific sales strategies for healthcare providers.

• Assist AEs in engaging CMOs and senior marketing leaders with business cases related to patient acquisition, marketing performance, digital advertising, and data privacy.

• Identify effective approaches, convert them into repeatable strategies, and promote adoption across the team.

• Achieve $6–8 million in new-business ARR in FY2027 and enhance Freshpaint’s leadership in the healthcare provider market.

⛳️ Requirements

• Proven experience in B2B sales leadership, managing, coaching, and developing quota-carrying Account Executives, with a demonstrated history of meeting or exceeding team revenue goals.

• Direct, successful closing experience as an Account Executive, with a proven track record of meeting or surpassing quotas and independently navigating complex sales situations.

• Strong experience selling to CMOs, senior marketing executives, and business decision-makers, ideally 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, encompassing consultative discovery, value-based selling, executive engagement, multi-threading, negotiations, and closing.

• Proven coaching skills and experience enhancing AE performance, developing talent, and building high-performing sales teams.

• Strong grasp of MEDDPICC and structured sales methodologies.

• Excellent pipeline management and forecasting abilities.

• Demonstrated capability to create and implement repeatable sales strategies, generate pipeline, enhance win rates, and ensure consistent sales execution across various segments.

• Hands-on, player-coach leadership approach.

• Strong communication, organizational, and leadership competencies.

• High ownership, adaptability, and a growth-oriented mindset.

• Experience selling to Regional Health Systems, Multi-location Specialty Practices, DSOs, Urgent Care, or Health Tech organizations (preferred).

• Familiarity with healthcare marketing, patient acquisition, digital advertising, marketing technology, and the healthcare provider buying landscape (preferred).

• Knowledge of HIPAA, data privacy, security reviews, and compliance-related challenges (preferred).

• Experience leading a mix of SMB, Mid-Market, and Enterprise Account Executives (preferred).

• Must reside within the United States; Freshpaint exclusively hires within the US.

🏝️ Benefits

• Competitive salary plus generous equity.

• Half-day Fridays every week.

• Fully paid parental leave for 16 weeks (eligible after 6 months; commission-based roles receive 100% base salary during leave).

• Flexible PTO with a mandatory minimum of 2 weeks.

• Comprehensive health, dental, and vision plans (100% coverage for you, 80% for dependents).

• Intentional and engaging company offsites.