Regional Vice President, Mid Market Sales - Omada Health

About the Role

Omada Health is seeking a proactive, resilient Regional Vice President, Mid Market Sales to grow our impact across the employer ecosystem. This is an individual contributor role focused on outbound prospecting, pipeline development, and winning new business within the mid-market segment.

What You’ll Do

Create and Develop Pipeline

• Own new-business development within your territory.
• Build and execute a focused territory strategy prioritizing target accounts and stakeholders.
• Maintain a consistent, proactive prospecting cadence through direct outreach, benefits consultants, and health plan partnerships.

Lead Discovery and Solve Customer Problems

• Lead thorough discovery to understand employer benefits strategies and business priorities.
• Move beyond surface-level requests to uncover underlying needs and decision criteria.
• Build credible business cases for senior leaders across Benefits, HR, and Finance.

Advance Opportunities and Deliver Results

• Own the full sales cycle from prospecting through contract closure.
• Navigate complex buying environments and competing priorities.
• Collaborate with cross-functional teams and strategic partners to drive results.

Maintain Accurate Sales Forecasting

• Maintain an accurate, up-to-date sales forecast based on confirmed engagement.
• Proactively identify deal risks and keep CRM records current.

What You’ll Bring

• Experience selling health and/or benefits solutions to self-insured employers.
• Demonstrated success in proactive outbound prospecting and territory development.
• Strong discovery and solution-based selling skills.
• Experience navigating complex sales cycles and engaging senior-level executives.
• Proven track record of quota achievement.
• Bachelor’s degree.
• Ability to reside in the western or midwestern United States.
• Ability to work Central Time business hours.
• Willingness to travel 25%–50% of the time.