Sales VP- Enterprise

We are seeking a strategic, results-driven enterprise sales leader to accelerate growth in the employee benefits administration and HR technology market. In this role, you will lead the full sales cycle for large, complex employers with 35,000 or more eligible employees, from prospecting and solution development to negotiations and contract execution. You will build trusted relationships with C-suite executives, HR and benefits leaders, procurement teams, consultants, and strategic partners. Working cross-functionally with product, technology, finance, legal, implementation, and client services teams, you will develop tailored solutions that address complex organizational needs. This opportunity is ideal for a commercially minded professional who thrives in consultative enterprise sales, navigates lengthy buying cycles, and consistently turns strategic opportunities into long-term client partnerships.

• At least 10 years of experience in enterprise sales, strategic sales, or a comparable client-facing business development role.

• Demonstrated success selling benefits administration, HR technology, insurance, or SaaS solutions to large enterprise organizations.

• Direct experience selling to employers with 35,000 or more eligible employees.

• A proven ability to manage long, complex sales cycles involving multiple stakeholders and significant commercial considerations.

• Experience presenting and selling to senior decision-makers, including CHROs, CFOs, benefits executives, IT leaders, procurement teams, and other C-suite stakeholders.

• Strong understanding of benefits administration, enrollment technology, implementation processes, data integrations, and enterprise service delivery.

• Proven experience leading complex RFP processes, finalist presentations, pricing discussions, and contract negotiations.

• Ability to translate complex business and technical requirements into differentiated solutions and clear value propositions.

• Excellent executive communication, public speaking, presentation, negotiation, and relationship-management skills.

• Demonstrated ability to collaborate across product, technology, legal, finance, implementation, and client services functions.

• A bachelor’s degree or equivalent professional experience.

• Preferred: Experience selling SaaS solutions in HR technology, people technology, or employee benefits.

• Preferred: Established relationships with national benefits consultants, brokers, third-party administrators, or other enterprise-market influencers.

• Preferred: Experience selling to Fortune 500 companies or similarly complex organizations.

• Preferred: Experience structuring integrated solutions that combine multiple products, services, technology integrations, and implementation workstreams.

• Preferred: Familiarity with the operational, compliance, security, procurement, and contracting requirements of large enterprise employers.