Regional Vice President, Sales

Bicycle Health is seeking a Regional Vice President of Sales to drive regional expansion and accelerate revenue growth. Operating as a strategic subject matter expert in virtual substance use disorder solutions, you will lead a consultative, value-based sales approach to establish long-term health plan partnerships. In this role, you will engage C-suite decision-makers across Commercial, Medicaid, and ASO channels, guiding them through value-based care models that deliver measurable clinical and financial outcomes at scale.

Target Pay Range: $157,000-$200,000 + Commission + Equity - Compensation to be determined by the education, experience, knowledge, skills, and abilities of the applicant, internal equity, and alignment with market data.

Benefits:

• Discretionary PTO + 8.5 days of additional sick time + 10 paid holidays
• Paid parental leave
• 100% Employer Paid Employee Medical, Dental, and Vision Insurance
• Employer Paid STD & LTD
• 401k
• $50 monthly Remote Work Stipend

What you'll do:

• Provide Strategic & Operational Leadership
  • Co-develop and implement regional strategies aligned with overall business objectives
  • Set and execute the regional commercial strategy to rapidly expand market presence across commercial health plans, Medicaid, ASO channels, and self-funded employers.
  • Lead the end-to-end partnership lifecycle—from initial C-suite engagement and complex value proposition discovery through contract negotiation, deal execution, and account expansion.
  • Oversee sales productivity, deal-stage conversion discipline, qualified pipeline coverage, and new logo progression across all regional channels.
  • Partner with Regional Medical Director to make data-informed decisions regarding processes and operations to improve regional performance and patient experience across all interaction channels.
• Payer Relationship Management
  • Cultivate, deepen, and expand C-suite and VP-level relationships with health plan commercial leaders, product/solution leaders, medical directors, and network contracting officers, and support new logo growth and partnership expansions.
  • Serve as a strategic partner to health plan decision-makers, positioning Bicycle Health as a differentiated SUD solution within commercial, Medicaid and ASO payer channels.
  • Support in engaging with consultants and brokers to drive awareness, preference, and co-selling opportunities across payer and ASO channels.
• Value Communication & Sales Enablement
  • Use a consultative, value-based selling approach to translate Bicycle Health's clinical model, outcomes data, utilization impact, and total cost-of-care savings into compelling ROI narratives tailored to payer P&L’s including understanding how Bicycle solutions can impact MLR, VBC and ASO sales and account management teams.
  • Partner with payer teams to develop effective sales materials, data-driven proposals, claims-based ROI analyses, and population health assessments.
• Cross-Functional Collaboration
  • Coordinate with Bicycle Health’s Provider Sales, Implementation, Clinical Operations, and Client Success.
  • Provide market intelligence back to Product, Marketing, and Leadership to inform positioning, competitive differentiation, and solution roadmap priorities.
• Reporting & Forecasting
  • Maintain accurate pipeline and activity data in CRM (Hubspot), providing monthly forecasts, deal status updates, pipeline coverage reporting, and progress against bookings and new logo targets to sales leadership.
  • Track regional competitive dynamics and report on win/loss trends, pricing sensitivity, and objection patterns.

What we are looking for:

• Education: Bachelor’s degree in Business, Healthcare Administration, or related field (Master’s or MBA preferred).
• Experience: 10+ years of progressive B2B healthcare sales experience, with at least 5 years focused on health plan partnership development (Behavioral health experience preferred)
• Management: 5+ years in a senior management/director-level role overseeing operational teams, multi-site or regional footprints, and cross-functional staff in a high-growth healthcare delivery organization.
• Proven track record as a top-performing individual contributor closing complex, enterprise-level digital health, behavioral health, or virtual care contracts.
• Deep familiarity with Medicaid, Commercial and ASO self-funded plan mechanics and structures.
• Experience indirectly selling point solutions, specialty benefits, or value-based care programs through health plan ASO partnerships.
• Strong financial acumen; ability to build and present ROI models, total cost-of-care analyses, and actuarial summaries.
• Excellent communication, executive presence, and presentation skills — comfortable engaging CMOs, CFOs, commercial leaders, and network leaders.
• High EQ. Having the ability to read the room, read the situation and not sell features.
• Ability to travel up to 30% within the assigned region and to trade shows and conferences.

This is a full-time (40hrs per week) remote position.

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