Regional Vice President, Mid Market Sales

Omada Health is on a mission to bend the curve of chronic disease.

As a Regional Vice President, Mid Market Sales, you will play a critical role in growing Omada's impact across the employer ecosystem. This is an individual contributor role for a proactive, resilient sales professional who thrives on creating opportunities and winning new business.

Key Responsibilities:

Create and Develop Pipeline:

• Own new-business development within your territory, identifying and engaging employers that are a strong fit for Omada's solutions.
• Build and execute a focused territory strategy that prioritizes target accounts, relevant stakeholders, and opportunities for growth.
• Maintain a consistent, proactive prospecting cadence through direct outreach, benefits consultant relationships, and health plan partnerships.
• Use thoughtful, persistent follow-up and tailored messaging to earn conversations and develop qualified opportunities.
• Sustain pipeline-building activity while managing active opportunities and advancing deals toward closure.
• Evaluate what is working, adapt your approach, and find new ways to engage accounts when initial efforts do not produce results.

Lead Discovery and Solve Customer Problems:

• Lead thorough discovery to understand each employer's benefits strategy, business priorities, current challenges, and desired outcomes.
• Move beyond surface-level requests to uncover underlying needs, the impact of existing challenges, and the reasons a customer would take action.
• Understand stakeholder perspectives, decision criteria, buying processes, and potential barriers early in the sales cycle.
• Develop tailored recommendations that connect Omada's solutions to the customer's specific needs rather than relying on a standard product presentation.
• Build a credible business case and communicate it effectively to senior leaders across Benefits, HR, and Finance.

Advance Opportunities and Deliver Results:

• Own the full sales cycle, from prospecting and qualification through proposal, negotiation, and contract closure.
• Build relationships across stakeholders and navigate complex buying environments with competing priorities.
• Establish clear, mutually agreed-upon next steps and maintain momentum throughout the sales process.
• Identify obstacles, address concerns, and develop practical strategies to move opportunities forward.
• Collaborate with benefits consultants, strategic partners, and health plans on territory, account, and opportunity strategies.
• Take accountability for pipeline development, sales execution, and quota achievement.

Maintain Accurate Sales Forecasting:

• Maintain an accurate, up-to-date sales forecast grounded in customer engagement, confirmed next steps, and a clear understanding of the buying process.
• Critically assess opportunity stage, close timing, and likelihood to close using evidence from discovery and deal progression,not optimism alone.
• Proactively identify and communicate deal risks, stalled opportunities, and changes in timing, along with a plan to address them.
• Keep CRM records current, including stakeholder engagement, 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.

Requirements:

• Experience selling health and/or benefits solutions to self-insured employers.
• Demonstrated success generating qualified pipeline through proactive outbound prospecting and sustained territory development.
• A track record of winning new business in challenging territories through persistence, resourcefulness, and disciplined execution.
• Strong discovery skills, including the ability to uncover underlying business problems, clarify priorities, and understand the implications of leaving challenges unresolved.
• Proven solution-based selling skills, with the ability to translate discovery insights into tailored recommendations and a compelling business case.
• Experience navigating complex sales cycles and engaging senior-level executives in Benefits, HR, and Finance.
• Experience working with benefits consultants at both regional and national levels.
• Experience collaborating with health plan account managers.
• A record of successful quota achievement and clear ownership of results.
• Strong presentation, communication, and listening skills.
• The self-direction to manage your territory independently, prioritize effectively, and maintain prospecting momentum.
• 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 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 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