Regional Vice President – Mid Market Sales

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

📋 Description

• Expand Omada Health’s influence within the employer ecosystem by creating new business opportunities for its virtual-first chronic-care healthcare programs.

• Take charge of new business development in the designated territory and identify as well as engage employers that align with Omada’s solutions.

• Formulate and implement territory strategies that prioritize target accounts, key stakeholders, and avenues for growth.

• Conduct proactive prospecting through direct outreach, building relationships with benefits consultants, and collaborating with health plan partners.

• Lead discovery sessions to comprehend employers’ benefits strategies, priorities, challenges, decision-making criteria, purchasing processes, and desired outcomes.

• Create customized recommendations and persuasive business cases for Benefits, HR, and Finance leaders.

• Manage the complete sales cycle from prospecting and qualification to proposal development, negotiation, and contract finalization.

• Cultivate relationships with stakeholders and navigate intricate buying environments.

• Define next steps, overcome obstacles, and sustain sales momentum.

• Work in partnership with benefits consultants, strategic partners, and health plans on territory, account, and opportunity strategies.

• Take responsibility for pipeline development, sales execution, and achieving sales quotas.

• Keep precise sales forecasts and up-to-date CRM records.

• Identify and communicate potential deal risks, stalled opportunities, and changes in timing.

• Engage in regular pipeline and forecast reviews.

⛳️ Requirements

• Proven experience in selling health and/or benefits solutions to self-insured employers.

• Demonstrated success in generating a qualified pipeline through proactive outbound prospecting and consistent territory development.

• A history of acquiring new business in challenging territories through persistence, resourcefulness, and disciplined execution.

• Strong discovery capabilities, including the ability to identify underlying business issues, clarify priorities, and understand the implications of unresolved challenges.

• Proven solution-based selling skills, with the ability to translate discovery insights into customized recommendations and a compelling business proposition.

• Experience in navigating complex sales cycles and engaging with senior-level executives in Benefits, HR, and Finance.

• Familiarity with working alongside benefits consultants at both regional and national levels.

• Experience collaborating with health plan account managers.

• A record of achieving sales quotas and taking clear ownership of results.

• Strong presentation, communication, and listening skills.

• The ability to independently manage your territory, prioritize effectively, and maintain continuous prospecting efforts.

• Resilience in the face of rejection, stalled opportunities, or challenging sales cycles, along with the judgment to adapt your approach.

• Previous experience in an emerging-growth company.

• Bachelor’s degree.

• Candidates must be residents of the western or midwestern United States.

• Ability to work Central Time business hours and support customers and partners across Pacific, Mountain, and Central time zones.

• Willingness to travel approximately 25%–50% of the time within the territory.

🏝️ Benefits

• Competitive salary with a generous annual cash bonus.

• Equity grants.

• Employee stock purchasing plan (ESPP).

• Remote-first work-from-home culture.

• Flexible Time Off to allow you to rest, recharge, and connect with loved ones.

• Generous parental leave.

• Health, dental, and vision insurance with above-market employer contributions.

• 401k retirement savings plan.

• Lifestyle Spending Account (LSA).

• Mental Health Support Solutions.