Regional Vice President, Enterprise Sales - Omada Health

Omada Health is on a mission to inspire and enable people everywhere to live free of chronic disease. Employers are a critical part of that mission, sponsoring access to Omada's programs for their employees.

With 29 peer-reviewed publications demonstrating clinical and economic outcomes and a pay-for-performance business model, Omada is looking for a Regional Vice President, Enterprise Sales to grow our impact with the nation's largest self-insured employers.

This is an individual contributor role focused on new-logo acquisition. You will own a territory of named enterprise prospects, typically employers with 10,000 or more covered lives, and be responsible for turning those accounts into Omada customers. Success requires a disciplined, account-based approach to prospecting, managing 6–12 month sales cycles, and full ownership of pipeline development. You will work closely with national and regional benefits consultants, health plans, and PBM partners.

This position reports to the National VP and works collaboratively across Omada's sales organization and cross-functional teams.

What You'll Do

Create and Develop Enterprise Pipeline

• Own new-logo business development for a territory of named enterprise prospects (10,000+ covered lives).
• Build and execute a multi-year territory plan prioritizing target accounts based on fit, timing, benefits strategy, and buying triggers.
• Develop account-level plans for priority prospects mapping organizational structure, key stakeholders, influencers, consultant relationships, and incumbent vendors.
• Run a consistent, account-based prospecting cadence through executive outreach, benefits consultant relationships, and health plan/PBM partnerships.
• Engage multiple stakeholders within each account to build early relationships ahead of formal buying processes.
• Sustain pipeline-building activity across named accounts while managing active, long-cycle opportunities toward closure.

Lead Discovery and Solve Executive-Level Problems

• Lead thorough, multi-threaded discovery to understand each employer's benefits strategy, workforce health priorities, cost drivers, and point-solution landscape.
• Move beyond surface-level requests to uncover underlying needs, quantify challenge impact, and identify compelling reasons to act.
• Identify economic buyers, champions, decision criteria, decision process, and paper process early.
• Develop tailored recommendations connecting Omada's multi-condition platform to customer needs and existing vendor/PBM arrangements.
• Build a credible, data-driven business case (ROI and cost-of-inaction analysis) and present to senior leaders across Benefits, Total Rewards, HR, and Finance.

Orchestrate Complex Enterprise Deals

• Own the full new-business sales cycle, from prospecting and qualification through consultant-led evaluations, RFPs, finalist presentations, contracting, and close.
• Build and maintain mutual action plans with customers defining milestones, owners, and timelines across 6–12 month cycles.
• Navigate enterprise buying processes including procurement, legal, security/privacy review, and data-sharing requirements.
• Lead an internal deal team including solutions consultants, clinical/analytics experts, legal, implementation, and executive sponsors.
• Partner with national and regional benefits consultants on account strategy, RFP responses, and finalist positioning.
• Lead complex negotiations on pricing, performance guarantees, and contract terms with Deal Desk and Legal.
• Ensure a clean handoff to Account Management and Client Success post-close.

Maintain Accurate Sales Forecasting

• Maintain an accurate forecast grounded in customer engagement, confirmed next steps, and clear understanding of enterprise buying processes.
• Apply a structured qualification framework (such as MEDDPICC) to inspect deals consistently over long cycles.
• Proactively identify and communicate deal risks, stalled opportunities, and timeline changes.
• Keep CRM records current, including account plans, stakeholder maps, decision criteria, and approval processes.

What You'll Bring

• Experience: 5+ years of experience selling health and/or benefits solutions to large self-insured employers (10,000+ employees/covered lives).
• Track Record: Demonstrated success winning new logos through proactive, account-based prospecting and sustained territory development.
• Sales Cycle Management: Experience managing long, complex sales cycles of 6–12+ months involving formal evaluations and RFPs.
• Methodology & Execution: Experience using structured qualification methodologies (e.g., MEDDPICC) to manage pipeline and forecasting.
• Executive Presence: Ability to engage C-suite and senior leaders across Benefits, Total Rewards, HR, and Finance.
• Ecosystem Partnerships: Established relationships with national and regional benefits consulting firms, health plan teams, and PBM account teams.
• Contracting: Experience negotiating enterprise contracts, pricing, performance guarantees, and procurement terms.
• Growth Background: Experience working in an emerging-growth company.
• Education: Bachelor's degree.

Location and Travel

• Candidates must reside in the Midwestern United States (Illinois preferred).
• Ability to work Central Time business hours and support customers across Central and Eastern time zones.
• Willingness to travel approximately 25%–50% within the territory for onsite executive meetings, finalist presentations, and consultant meetings.

Benefits

• Competitive salary with generous annual cash bonus
• Equity grants & Employee Stock Purchase Plan (ESPP)
• Remote-first work culture
• Flexible Time Off (FTO) & generous parental leave
• Health, dental, and vision insurance with high employer contributions
• 401(k) retirement savings plan
• Lifestyle Spending Account (LSA) & mental health support solutions

About Omada Health

Omada Health (Nasdaq: OMDA) is reverse engineering the way healthcare is delivered in America. Omada’s virtual-first model combines human-led care teams, connected devices, and AI-enabled technology to deliver personalized care at scale across obesity, diabetes, hypertension, cholesterol, and musculoskeletal conditions.