Regional Vice President, Mid Market Sales

Omada Health

20h•$244,800 - $299,400•Remote

About The Position

Omada Health is hiring a Regional Vice President, Mid Market Sales to grow its impact among employers that sponsor access to Omada’s chronic disease programs. This is an individual-contributor sales role for a proactive, resilient seller who develops new business through disciplined outbound prospecting and ownership of pipeline development. The role works closely with benefits consultants and health plan partners, while independently generating opportunities rather than relying solely on inbound interest or referrals. The successful candidate uses discovery-led, solution-based selling to understand employers’ benefits strategies, priorities, challenges, and desired outcomes. They translate those insights into tailored recommendations and compelling business cases for senior leaders, navigate complex buying environments, and own the complete sales cycle from prospecting through contract closure. The position reports to the National VP and collaborates with Omada’s sales organization and cross-functional teams. Candidates must reside in the western or midwestern United States, be able to work Central Time business hours, and support customers and partners across Pacific, Mountain, and Central time zones. The role requires approximately 25%–50% travel within the territory. The posted OTE ranges by zone are $263,520–$299,400 in Zone 1, $257,280–$291,600 in Zone 2, and $244,800–$276,000 in Zone 3. OTE includes base pay and commission at 100% of target; base salary is approximately 51%–60% of the total compensation range. The role is also eligible for equity grants.

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.
Track record of winning new business in challenging territories through persistence, resourcefulness, and disciplined execution.
Strong discovery skills, including uncovering underlying business problems, clarifying priorities, and understanding the implications of unresolved challenges.
Proven solution-based selling ability, including translating 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 regional and national levels.
Experience collaborating with health plan account managers.
Record of quota achievement and clear ownership of results.
Strong presentation, communication, and listening skills.
Ability to manage a territory independently, prioritize effectively, and maintain prospecting momentum.
Resilience in the face of rejection, stalled opportunities, and difficult sales cycles, with judgment to adapt the approach.
Experience working in an emerging-growth company.
Bachelor’s degree.
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.

Responsibilities

Own new-business development within the assigned territory by identifying and engaging employers that fit Omada’s solutions.
Build and execute a focused territory strategy that prioritizes target accounts, stakeholders, and growth opportunities.
Prospect proactively through direct outreach, benefits consultant relationships, and health plan partnerships; use persistent follow-up and tailored messaging to develop qualified opportunities.
Maintain pipeline-building activity while managing active opportunities, adapt prospecting approaches when needed, and advance deals toward closure.
Lead thorough discovery into employers’ benefits strategies, business priorities, challenges, desired outcomes, stakeholder perspectives, decision criteria, buying processes, and barriers.
Develop tailored recommendations and compelling business cases that connect Omada’s solutions to employers’ specific needs, and communicate them to senior leaders in Benefits, HR, and Finance.
Own the full sales cycle from prospecting and qualification through proposal, negotiation, and contract closure.
Build stakeholder relationships, navigate complex buying environments, establish agreed-upon next steps, maintain sales momentum, and address obstacles and concerns.
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 an accurate sales forecast based on customer engagement, confirmed next steps, buying-process knowledge, evidence-based stage and close assessments, and clear risk plans.
Keep CRM records current, participate in pipeline and forecast reviews, communicate deal risks and timing changes, and articulate what must happen for opportunities to close.