Sales VP – Enterprise

This is a fully remote position, open to applicants in United States.

📋 Description

• Propel growth in bswift’s enterprise market by marketing benefits administration technology and services to employers with 35,000 or more eligible lives.

• Take ownership of the entire sales cycle, from prospecting and opportunity development to RFP responses, solution design, pricing, contract negotiations, and closure.

• Serve as the representative for bswift’s technology and benefits administration services to enterprise employers.

• Formulate and implement targeted sales strategies for intricate enterprise prospects.

• Cultivate relationships with senior client executives, benefits consultants, brokers, enrollment firms, and strategic partners.

• Prospect within designated enterprise markets and create a qualified jumbo-market opportunity pipeline.

• Lead discovery sessions, solution development, RFP responses, finalist presentations, pricing discussions, negotiations, and contract execution.

• Evaluate prospect business, technology, service, integration, communication, and employee experience needs.

• Coordinate efforts with Solution Architecture, Product, Technology, Legal, Finance, Implementation, and Client Services teams.

• Direct internal preparations for external sales meetings, presentations, and finalist discussions.

• Develop and deliver presentations that showcase bswift’s capabilities, differentiation, and business value.

• Navigate complex buying groups across benefits, HR, finance, IT, procurement, legal, and executive leadership.

• Oversee negotiations related to pricing, service models, implementation requirements, performance commitments, and contractual terms.

• Position bswift’s array of technology, benefits administration, communication, and related services effectively.

• Build relationships with market influencers and maintain visibility at industry events and forums.

• Ensure accurate enterprise pipeline visibility, including status, risks, next steps, and projected closing timelines.

• Collaborate with implementation and client teams to facilitate the transition from sales through contracting and implementation.

⛳️ Requirements

• Over 10 years of experience in enterprise sales, strategic sales, or a comparable client-facing growth position.

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

• Proven track record of selling to employers with 35,000 or more eligible lives.

• Experience managing lengthy, complex sales cycles that involve multiple business and technical stakeholders.

• Skilled in developing and presenting solutions to CHROs, CFOs, benefits executives, IT leaders, procurement teams, and other senior decision-makers.

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

• Experience leading complex RFP responses, finalist presentations, pricing discussions, and contract negotiations.

• Capability to translate complex client needs into clear, differentiated solutions and business value.

• Exceptional public speaking, executive presentation, negotiation, and relationship management skills.

• Ability to collaborate effectively across Product, Technology, Legal, Finance, Implementation, and Client Services.

• Bachelor’s degree or equivalent professional experience.

• Preferred: experience in selling SaaS solutions in the People, HR technology, or employee benefits sector.

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

• Preferred: experience providing benefits administration solutions to Fortune 500 or similarly complex organizations.

• Preferred: experience structuring solutions involving multiple products, services, integrations, and implementation workstreams.

• Preferred: familiarity with the operational, compliance, security, procurement, and contracting needs of jumbo-market employers.

🏝️ Benefits

• Health, dental, and vision plans.

• Performance-based incentives for most roles.

• Remote-first, office-friendly environment.

• Employer-sponsored retirement savings programs.

• Professional development opportunities, training, and career resources.

• Supportive, collaborative culture.

• Mental health, financial planning, and wellness resources.

• Flexible and creative work environment.

• Standard working hours of 8am-5pm Central Time.