Regional Vice President, Mid Market Sales

Remote, USA

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

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.

• 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 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.

• 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…