Sales VP- Enterprise

bswift

2d • $150,000 - $175,000 • Remote

About The Position

The Sales VP, Enterprise drives growth within bswift’s enterprise market by selling benefits administration technology and services to large, complex employers with 35,000 or more eligible lives. The role owns the full sales cycle, from proactive prospecting and opportunity development through discovery, solution design, RFP response, finalist presentations, pricing strategy, contract negotiation, execution, and close.

The position builds relationships with senior decision-makers and market partners, including CHROs, CFOs, benefits leaders, procurement and IT executives, consultants, brokers, and enrollment firms. It requires navigating complex, multi-stakeholder sales processes; assessing client business, technology, service, integration, communication, and employee-experience needs; and coordinating internal teams to develop tailored solutions. The role also maintains pipeline visibility and partners with implementation and client teams to support transition from sales through contracting and implementation.

bswift describes its environment as collaborative, dynamic, inclusive, remote-first and office-friendly, with opportunities for professional and personal growth. Standard working hours are 8 a.m.–5 p.m. Central Time unless otherwise stated.

Requirements

• 10+ years of experience in enterprise sales, strategic sales, or a comparable client-facing growth role.
• Proven success selling benefits administration, HR technology, insurance, or SaaS solutions to large enterprise employers.
• Experience selling to employers with 35,000 or more eligible lives.
• Demonstrated success managing long, complex sales cycles involving multiple business and technical stakeholders.
• Experience developing and presenting solutions to CHROs, CFOs, benefits executives, IT leaders, procurement teams, and other senior decision-makers.
• Strong understanding 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.
• Ability to translate complex client needs into clear, differentiated solutions and business value.
• Strong 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.

Nice To Haves

• Experience selling SaaS solutions in the People, HR technology, or employee benefits space.
• Established relationships with national benefits consultants, brokers, third-party administrators, or other enterprise-market influencers.
• Experience selling benefits administration solutions to Fortune 500 or similarly complex organizations.
• Experience structuring solutions that include multiple products, services, integrations, and implementation workstreams.
• Familiarity with the operational, compliance, security, procurement, and contracting requirements of jumbo-market employers.

Responsibilities

• Represent bswift’s technology and benefits administration services to enterprise employers with 35,000 or more eligible lives.
• Develop and execute targeted sales strategies for complex enterprise prospects.
• Build and maintain relationships with senior client executives, benefits consultants, brokers, enrollment firms, and other strategic partners.
• Proactively prospect within assigned enterprise markets and develop a qualified pipeline of jumbo-market opportunities.
• Lead the full enterprise sales cycle, including discovery, solution development, RFP responses, finalist presentations, pricing, negotiations, and contract execution.
• Assess prospects’ business, technology, service, integration, communication, and employee-experience needs to develop tailored solutions.
• Coordinate internal teams throughout the sales process, including Solution Architecture, Product, Technology, Legal, Finance, Implementation, and Client Services.
• Lead internal strategy and preparation sessions for external sales meetings, presentations, and finalist discussions.
• Create and deliver presentations communicating bswift’s capabilities, differentiation, and business value.
• Navigate complex buying groups across benefits, HR, finance, IT, procurement, legal, and executive leadership.
• Manage negotiations involving pricing, service models, implementation requirements, performance commitments, and contract terms.
• Identify opportunities to position bswift’s portfolio of technology, benefits administration, communication, and related services.
• Develop relationships with key market influencers and maintain a presence at industry events and forums.
• Maintain an accurate enterprise pipeline and provide visibility into opportunity status, risks, next steps, and projected close timing.
• Partner with internal implementation and client teams to support a smooth transition from sales through contracting and implementation.

Benefits

• Health, dental, and vision plans.
• Competitive compensation, including performance-based incentives for most roles.
• Remote-first, office-friendly work environment.
• Employer-sponsored retirement savings programs.
• Professional development opportunities, training, and career-progression resources.
• Supportive culture that encourages collaboration, open communication, and creative problem-solving.
• Employee wellbeing initiatives, including mental health, financial planning, and wellness resources.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive