Regional Vice President, Enterprise Sales

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 only 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, the patience and rigor to manage 6–12 month sales cycles, and full ownership of pipeline development.

Create and Develop Enterprise Pipeline

• Own new-logo business development for a territory of named enterprise prospects, typically self-insured employers with 10,000+ covered lives.
• Build and execute a multi-year territory plan that prioritizes target accounts based on fit, timing, benefits strategy, and buying triggers such as consultant reviews, plan renewals, and vendor consolidation.
• Develop account-level plans for priority prospects that map the 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 and PBM partnerships.
• Engage multiple stakeholders within each account to build early relationships, often well before a formal buying process begins.
• Sustain pipeline-building activity across your named accounts while managing active, long-cycle opportunities toward closure.
• Evaluate what is working, adapt your approach, and find new paths into accounts when initial efforts do not produce results.

Lead Discovery and Solve Executive-Level Problems

• Lead thorough, multi-threaded discovery to understand each employer's benefits strategy, workforce health priorities, cost drivers, point-solution landscape, and desired outcomes.
• Move beyond surface-level requests to uncover underlying needs, quantify the impact of existing challenges, and identify the compelling reasons an enterprise would act.
• Identify economic buyers, champions, decision criteria, decision process, and paper process early, and validate them throughout the cycle.
• Develop tailored recommendations that connect Omada's multi-condition platform to the customer's specific needs, existing vendor ecosystem, and health plan or PBM arrangements.
• Build a credible, data-driven business case, including ROI and cost-of-inaction analysis, and present it effectively 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 that define milestones, owners, and timelines across 6–12 month cycles.
• Navigate enterprise buying processes that include procurement, legal, security and privacy review, data-sharing requirements, and health plan or PBM coordination.
• Lead an internal deal team that may include solutions consultants, clinical and 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 in partnership with Deal Desk and Legal.
• Ensure a clean handoff to Account Management and Client Success after close so new customers launch successfully.
• Take accountability for pipeline development, sales execution, and quota achievement.

Maintain Accurate Sales Forecasting

• Maintain an accurate, up-to-date forecast grounded in customer engagement, confirmed next steps, and a clear understanding of each enterprise buying process.
• Critically assess opportunity stage, close timing, and likelihood to close using evidence from discovery and deal progression,not optimism alone.
• Apply a structured qualification framework, such as MEDDPICC, to inspect deals consistently over long cycles.
• Proactively identify and communicate deal risks, stalled opportunities, and changes in timing, along with a plan to address them.
• Keep CRM records current, including account plans, stakeholder maps, decision criteria, approval processes, and outstanding milestones.
• Participate in regular pipeline and forecast reviews, clearly articulating what must happen for each opportunity to close and taking accountability for forecast accuracy.

What You'll Bring

• 5+ years of experience selling health and/or benefits solutions to large self-insured employers, including a track record of closing enterprise deals with organizations of 10,000+ employees or covered lives.
• Demonstrated success winning new logos through proactive, account-based prospecting and sustained development of a named-account territory.
• Experience managing long, complex sales cycles of 6–12 months or more with multiple stakeholders, formal evaluations, and RFPs.
• Strong discovery skills, including the ability to uncover underlying business problems, quantify their impact, and understand the implications of leaving challenges unresolved.
• Proven solution-based selling skills, with the ability to build a tailored, financially grounded business case for executive audiences.
• Executive presence and experience engaging C-suite and senior leaders in Benefits, Total Rewards, HR, and Finance.
• Established relationships with, and experience working alongside, national and regional benefits consulting firms.
• Experience collaborating with health plan and PBM account teams in large employer accounts.
• Experience negotiating enterprise contracts, including pricing, performance guarantees, and procurement and legal terms.
• Experience using a structured qualification methodology (such as MEDDPICC) to manage pipeline and forecast accurately.
• A consistent record of quota achievement and clear ownership of results.
• Strong presentation, communication, and listening skills.
• The self-direction to manage a named-account territory independently, prioritize effectively, and maintain momentum over long cycles.
• Resilience when faced with rejection, stalled opportunities, or difficult sales cycles,and the judgment to adapt your approach.
• Experience working in an emerging-growth company.
• Bachelor's degree.

Location and Travel

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

Benefits

• Competitive salary with generous annual cash bonus
• Equity grants
• Employee stock purchasing plan (ESPP)
• Remote first work from home culture
• Flexible Time Off to help you rest, recharge, and connect with loved ones
• Generous parental leave
• Health, dental, and vision insurance (and above market employer contributions)
• 401k retirement savings plan
• Lifestyle Spending Account (LSA)
• Mental Health Support Solutions