Regional Vice President, Mid Market Sales

Job overview

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, Mid Market Sales to grow our 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. Success requires a disciplined approach to outbound prospecting, persistent follow-through, and ownership of pipeline development. You will work closely with benefits consultants and health plan partners while taking responsibility for generating opportunities-not relying solely on inbound interest or partner referrals.

Just as important, you are a skilled solution-based seller who leads with discovery rather than a product pitch. You ask thoughtful questions, uncover underlying challenges, and understand the customer's priorities before recommending a solution. You can translate those insights into a compelling business case that connects Omada's capabilities to the outcomes that matter most to each employer.

The ideal candidate combines drive and tenacity with curiosity, sound judgment, and integrity. They are comfortable navigating complex buying environments, engaging senior executives, and finding a path forward when opportunities stall. They care deeply about their craft, their customers, and the relationships they build across the healthcare ecosystem.

This position reports to the National VP and works collaboratively across Omada's sales organization and cross-functional teams.

What You'll Do

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.

What You'll Bring

• 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

-...and more!

• It takes a village to change health care.
• As we build together toward our mission, we strive to embody the following values in our day-to-day work.
• We hope these hold meaning for you as well as you consider Omada!

• Cultivate Trust. We listen closely and we operate with kindness. We provide respectful and candid feedback to each other.
• Seek Context. We ask to understand and we build connections. We do our research up front to move faster down the road.
• Act Boldly. We innovate daily to solve problems, improve processes, and find new opportunities for our members and customers.
• Deliver Results. We reward impact above output. We set a high bar, we're not afraid to fail, and we take pride in our work.
• Succeed Together. We prioritize Omada's progress above team or individual. We have fun as we get stuff done, and we celebrate together.
• Remember Why We're Here. We push through the challenges of changing health care because we know the destination is worth it.