Vice President, Jumbo & Enterprise Employer Sales

This is a fully remote position, open to applicants in California, +2 more states.

📋 Description

• Responsible for all execution and operational outcomes pertaining to new business development in the Jumbo and Enterprise segments.

• Formulates and propels immediate strategic priorities for enterprise sales, ensuring alignment with corporate goals and growth aspirations.

• Supplies business intelligence and recommendations to executive leadership to shape the broader commercial strategy and identify expansion opportunities.

• Maintains accurate forecasting, pipeline integrity, and operational discipline across the national jumbo and enterprise sales organization.

• Converts abstract growth objectives into actionable national sales strategies focused on measurable results, team accountability, and enterprise impact.

• Provides decisive leadership and strategic guidance in navigating complex negotiations, unclear deal structures, or changing market conditions.

• Advocates for innovation in sales process design, incentive structures, and go-to-market readiness for large enterprise customers.

• Holds a comprehensive understanding of industry dynamics, including trends in employer benefits, competitive landscape, and health plan contracting frameworks.

• Anticipates shifts in the market as well as regulatory or competitive factors that affect enterprise employer purchasing behavior.

• Influences product and marketing teams to ensure Omada’s value proposition remains relevant, distinct, and responsive to market needs.

• Collaborates with other department and function leaders in marketing, channel sales, clinical, and product to ensure strategic alignment and organizational success.

• Represents Omada externally to C-suite stakeholders at national employers, consultants, and health plans, building trust-based partnerships that foster scale.

• Leads and develops a team of outstanding sales professionals, nurturing a culture of accountability, collaboration, and growth.

• Builds trust at all levels by being approachable, transparent, and receptive to feedback from peers, team members, and executives alike.

• Invests in the development of individuals, mentoring future leaders while cultivating a culture rooted in integrity, shared success, and mutual respect.

• Continuously inspires others by showcasing a strong commitment to Omada’s mission and values.

• Embodies a growth mindset, perseverance, and purpose-driven leadership, encouraging teams to achieve outcomes that enhance health at scale.

⛳️ Requirements

• 10–15 years of experience in leading enterprise sales or business development teams within the healthcare, digital health, or benefits ecosystem.

• Proven success in engaging C-suite executives at Fortune 500 employer accounts and national consulting firms.

• In-depth understanding of employer benefits strategy, purchasing frameworks, and health plan distribution networks.

• Strong strategic and analytical skills, capable of balancing long-term planning with operational execution.

• A history of leading teams to consistently exceed quotas.

• Outstanding communication, negotiation, and stakeholder management abilities.

• BA/BS required; MBA or advanced degree preferred.

🏝️ Benefits

• Competitive salary with a generous annual cash bonus

• Equity grants

• Remote-first work-from-home culture

• Flexible Time Off to assist you in resting, recharging, and connecting with loved ones

• Generous parental leave

• Health, dental, and vision insurance (with above-market employer contributions)

• 401k retirement savings plan

• Lifestyle Spending Account (LSA)

• Mental Health Support Solutions

• ...and more!