Regional Vice President, Enterprise Sales

Omada Health

1d•$283,200 - $345,850•Remote

About The Position

Omada Health is hiring an individual-contributor Regional Vice President, Enterprise Sales to acquire new enterprise customers and grow the company’s impact with large self-insured employers. The role owns a named territory of enterprise prospects, typically employers with at least 10,000 covered lives, and is responsible for developing pipeline, managing complex sales cycles, and achieving quota. It calls for a disciplined, account-based approach to prospecting and the ability to sustain momentum through sales cycles that commonly last 6–12 months. The position involves consultative, solution-based selling: leading discovery, understanding employers’ benefits strategies and business challenges, and developing tailored, financially grounded recommendations and business cases for executive audiences. The role works with benefits consultants, health plans, PBMs, customers, and internal cross-functional teams to navigate evaluations, RFPs, contracting, and implementation handoffs. It reports to the National VP. Candidates must reside in the Midwestern United States, with Illinois preferred, be able to work Central Time business hours, and be willing to travel approximately 25%–50% within the territory. The role is remote-first. The listed OTE ranges from $283,200 to $345,850 depending on salary zone, including base pay and commission at 100% target achievement; it is also eligible for equity grants.

Requirements

At least 5 years of experience selling health and/or benefits solutions to large self-insured employers.
A track record of closing enterprise deals with organizations of 10,000 or more employees or covered lives.
Demonstrated success winning new logos through proactive, account-based prospecting and sustained named-account territory development.
Experience managing complex sales cycles of 6–12 months or longer with multiple stakeholders, formal evaluations, and RFPs.
Strong discovery skills, including uncovering business problems, quantifying their impact, and assessing the consequences of inaction.
Proven solution-based selling skills and ability to build tailored, financially grounded business cases 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.
Consistent record of quota achievement and clear ownership of results.
Strong presentation, communication, and listening skills.
Ability to independently manage a named-account territory, prioritize effectively, and maintain momentum over long sales cycles.
Resilience in the face of rejection, stalled opportunities, or difficult sales cycles, and judgment to adapt approaches.
Experience working in an emerging-growth company.
Bachelor’s degree.
Residence 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% within the territory.

Responsibilities

Own new-logo business development for a territory of named enterprise prospects, typically self-insured employers with 10,000 or more covered lives.
Build and execute a multi-year territory plan that prioritizes target accounts according to fit, timing, benefits strategy, and buying triggers.
Develop account plans mapping organizational structures, stakeholders, influencers, consultant relationships, and incumbent vendors.
Prospect consistently through executive outreach, benefits consultant relationships, and health plan and PBM partnerships.
Build early relationships with multiple stakeholders and sustain pipeline development while managing active, long-cycle opportunities.
Evaluate prospecting effectiveness, adapt approaches, and identify new ways into accounts.
Lead thorough, multi-threaded discovery into employers’ benefits strategies, workforce health priorities, cost drivers, point-solution landscapes, and desired outcomes.
Uncover underlying business needs, quantify the impact of challenges, and identify compelling reasons for an employer to act.
Identify and validate economic buyers, champions, decision criteria, decision processes, and paper processes.
Develop tailored recommendations connecting Omada’s multi-condition platform to customer needs, vendor ecosystems, and health plan or PBM arrangements.
Build and present data-driven business cases, including ROI and cost-of-inaction analysis, to senior leaders.
Own the full new-business sales cycle, from prospecting and qualification through evaluations, RFPs, finalist presentations, contracting, and close.
Create and maintain mutual action plans with milestones, owners, and timelines across long sales cycles.
Navigate procurement, legal, security, privacy, data-sharing, and health plan or PBM coordination requirements.
Lead internal deal teams 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 pricing, performance-guarantee, and contract negotiations with Deal Desk and Legal.
Ensure a clean handoff to Account Management and Client Success after closing.
Take accountability for pipeline development, sales execution, and quota achievement.
Maintain an accurate forecast based on customer engagement, confirmed next steps, and a clear understanding of the buying process.
Assess opportunity stage, close timing, and likelihood to close using evidence from discovery and deal progression.
Apply a structured qualification framework, such as MEDDPICC, and proactively communicate deal risks and changes in timing.
Keep CRM records current, including account plans, stakeholder maps, decision criteria, approval processes, and outstanding milestones.
Participate in regular pipeline and forecast reviews and explain what must happen for opportunities to close.