Regional Vice President of Enterprise Sales

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. 

Forward-thinking employers use Espresa to consolidate point solutions, simplify benefits administration, increase employee engagement, and support the diverse needs of their workforce through a single, scalable platform. 

Join a growing team that is helping shape the future of employee benefits 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. This role focuses on developing and executing strategic account plans for a targeted portfolio of enterprise organizations, primarily those with 2,000+ employees, while also pursuing qualified opportunities across the broader U.S. market aligned with Espresa’s ideal customer profile. 

As a key member of the go-to-market team, this individual will lead complex, multi-stakeholder sales cycles with HR, Total Rewards, and Benefits 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. 

Executive Storytelling – Ability to translate Espresa’s vision and platform capabilities into compelling narratives that resonate with HR, Benefits, 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. 

What You’ll Do 

• Develop and execute strategic account plans for a targeted portfolio of enterprise employers, primarily organizations with 2,000+ employees.
• Lead complex enterprise sales cycles from initial engagement through contract execution, aligning Espresa’s platform to the priorities of HR, Total Rewards, and Benefits 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 consul