Espresa is a leading Personal

Benefits

platform that helps employers modernize how they support their people. Through a global, all-in-one platform, Espresa enables organizations to deliver Lifestyle Spending Accounts (LSAs), wellbeing programs, recognition, and employee engagement in a flexible and personalized way.

administration, increase employee engagement, and support the diverse needs of their workforce through a single, scalable platform.

and experience for large employers around the world. Role Overview The Regional Vice President of Enterprise Sales is responsible for driving new business growth with large employers across the United States. S.

market aligned with Espresa’s ideal customer profile.

leaders, often in collaboration with employer benefit consultants and broker partners. Success in this role requires strong discovery, value-based selling, and the ability to build trusted relationships with executive decision-makers. This role is ideal for a highly motivated enterprise seller who thrives in a fast-growing environment and enjoys helping shape how a category-defining platform expands within the large employer market.

What Makes You Successful in This Role Value-Based Selling – Ability to connect Espresa’s platform to meaningful business outcomes for HR and Total Rewards leaders, clearly articulating value beyond product features. Strategic Discovery – Skilled at uncovering organizational priorities, stakeholder dynamics, and business drivers within complex enterprise environments.

, and executive stakeholders. Relationship Building – Proven ability to build trusted relationships with senior decision-makers and influencers across large employer organizations. Enterprise Navigation – Experience managing complex, multi-stakeholder sales cycles and guiding organizations through evaluation, consensus building, and decision-making.

Team Selling Cross-Functional Collaboration – Comfortable operating in a team-selling environment, partnering closely with Strategic Alliances, Business Development, Solutions Consulting, Marketing, and Client Success to develop opportunities, engage consultant partners, and execute winning deal strategies. Ownership Mindset – Highly motivated and accountable, with the ability to operate independently and drive results in a fast-paced, entrepreneurial environment.

leaders. Build and manage relationships with key stakeholders and decision-makers within large employer organizations. Partner closely with Strategic Alliances to engage consultant and broker partners in consultant-influenced opportunities.

Collaborate with Business Development, Solutions Consulting, Marketing, and Client Success to develop opportunities and deliver a coordinated customer experience. Maintain a disciplined pipeline, delivering accurate forecasts and proactively managing deal progression and velocity across enterprise opportunities.

What You’Ll Do

Develop and execute strategic account plans for a targeted portfolio of enterprise employers, primarily organizations with 2,000+ employees.