National Vice President, Jumbo & Enterprise Employer Sales

About the role

The Senior Director, Jumbo & Enterprise Employer Sales is a senior-level leader responsible for shaping and executing Omada’s national new business growth strategy within the largest and most complex employer segments. This leader heads a strategic sales team accountable for driving revenue through Fortune 500 and large enterprise employers, and for leading the team responsible for the entire enterprise acquisition lifecycle from pipeline development to contracting.

Responsibilities

• Accountable for all execution and operational results related to new business growth in Jumbo and Enterprise segments.
• Develops and drives near-term strategic priorities for enterprise sales, ensuring alignment to corporate objectives and growth ambitions.
• Provides business intelligence and recommendations to executive leadership to influence broader commercial strategy and expansion opportunities.
• Owes accurate forecasting, pipeline integrity, and operational rigor across the national jumbo and enterprise sales organization.
• Translates abstract growth objectives into executable national sales strategies with an emphasis on measurable results, team accountability, and enterprise impact.
• Provides decisive leadership and strategic direction when navigating complex negotiations, ambiguous deal structures, or evolving market conditions.
• Champions innovation in sales process design, incentive structures, and go-to-market enablement for large enterprise customers.
• Possesses deep understanding of industry dynamics including employer benefits trends, competitive landscape, and health plan contracting frameworks.
• Anticipates market shifts and regulatory or competitive factors influencing enterprise employer purchasing behavior.
• Influences product and marketing teams to ensure Omada’s value proposition is relevant, differentiated, and responsive to market demand.
• Partners with other department and function leaders marketing, channel sales, clinical, and product to ensure strategic alignment and organizational success.
• Represents Omada externally with C-suite stakeholders at national employers, consultants, and health plans, cultivating trust-based partnerships that drive scale.
• Leads and develops a team of exceptional sales professionals, fostering a culture of accountability, collaboration, and growth.
• Buils trust across all levels approachable, transparent, and open to feedback from peers, team members, and executives alike.
• Invests in people’s development, mentoring future leaders while establishing a culture grounded in integrity, shared success, and mutual respect.

Qualifications

• 10–15 years’ experience leading enterprise sales or business development teams within healthcare, digital health, or benefits ecosystem.
• Demonstrated success engaging C-suite executives at Fortune 500 employer accounts and national consulting firms.
• Deep understanding of employer benefits strategy, purchasing frameworks, and health plan distribution networks.
• Strong strategic and analytical acumen able to balance long-term planning with operational execution.
• Track record of leading teams to deliver consistent quota overachievement.
• Exceptional communication, negotiation, and stakeholder management skills.

Benefits

• Competitive salary with generous annual cash bonus
• Equity grants
• 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