Sales VP- Enterprise

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Sales VP – Enterprise based in the United States . 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.

Represent enterprise benefits administration technology and services to large employers with 35,000 or more eligible employees. Develop and execute targeted sales strategies to penetrate enterprise markets, generate new business, and achieve revenue growth objectives. Build and maintain strong relationships with senior executives, benefits consultants, brokers, enrollment firms, and other strategic industry partners. Proactively identify prospective customers, cultivate relationships, and maintain a qualified pipeline of large-market opportunities. Own the complete enterprise sales cycle, including discovery, solution development, RFP responses, finalist presentations, pricing strategy, contract negotiations, and closing. Assess each prospect’s business objectives, technology environment, service expectations, integration requirements, communication needs, and employee experience priorities to create tailored solutions. Coordinate cross-functional teams across solution architecture, product, technology, legal, finance, implementation, and client services to develop compelling proposals and advance opportunities. Lead internal preparation and strategy sessions for customer meetings, executive presentations, and finalist discussions. Deliver persuasive presentations that communicate solution capabilities, competitive differentiation, and measurable business value. Navigate complex buying groups involving HR, benefits, finance, IT, procurement, legal, and executive leadership. Negotiate commercial arrangements covering pricing, service models, implementation requirements, performance commitments, and contractual terms. Identify opportunities to position a broad portfolio of benefits technology, administration, employee communications, and related services. Strengthen relationships with industry influencers and maintain an active presence at relevant conferences, events, and professional forums. Maintain accurate sales pipeline data and provide transparent updates on opportunity status, risks, next steps, and anticipated closing timelines. Partner with implementation and client teams to support a smooth transition from sales and contracting through solution delivery. Requirements: 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. Benefits: Base salary: $150,000–$175,000 annually, excluding fringe benefits and potential bonuses. Additional compensation: Performance-based incentives and a broader compensation package; specific incentive amounts are not stated. Health coverage: Medical, dental, and vision plans. Retirement savings: Employer-sponsored retirement savings programs. Remote-first flexibility: A remote-friendly work environment designed to support flexibility and work-life balance. Professional development: Training and resources to support ongoing learning and career progression. Employee wellbeing: Mental health, financial planning, and wellness resources. Collaborative culture: An inclusive environment that encourages creativity, accountability, open communication, and shared success. Meaningful impact: The opportunity to help organizations simplify benefits administration and improve the employee benefits experience. Working hours: Standard hours are 8:00 a.m. to 5:00 p.m. Central Time, unless otherwise specified. Compensation considerations: Final base salary depends on factors such as location, skills, education, experience, and internal pay equity. The stated range represents the full base salary range, and offers at the maximum are not typical. Benefits and specific offerings may vary by position and may change.