Enterprise Benefits Sales VP - Large-Scale Growth

Jobgether; United States; Remote; USD 150,000 - 175,000; Full time

Benefits offered by this job

Remote-friendly

Health coverage

Retirement savings

Professional development

Employee wellbeing

Collaborative culture

Job summary

Jobgether is seeking a strategic Sales VP – Enterprise to lead the full enterprise sales cycle in the United States, targeting large employers with 35,000+ eligible employees. You will build trusted relationships with CHROs, CFOs, benefits leaders, and procurement teams, and collaborate with product, technology, legal, and implementation groups to tailor solutions.

This role emphasizes consultative selling, long, multi-stakeholder buying cycles, RFP processes, pricing negotiations, and contract

Qualifications

• At least 10 years of experience in enterprise sales, strategic sales, or a comparable client-facing role.
• Proven success selling to large enterprise organizations.
• Direct experience selling to employers with 35,000+ eligible employees.
• Experience presenting to senior decision-makers (CHROs, CFOs, benefits executives, IT leaders).
• Strong understanding of benefits administration and enrollment technology.
• Experience leading complex RFP processes, pricing discussions, and contract negotiations.

Responsibilities

• Represent enterprise benefits administration technology and services to large employers with 35,000+ employees.
• Develop and execute targeted sales strategies to penetrate enterprise markets and achieve revenue growth.
• Build relationships with senior executives, brokers, and strategic partners.
• Own the complete enterprise sales cycle from discovery to closing.
• Coordinate cross-functional teams to develop tailored proposals and advance opportunities.
• Lead strategy sessions for customer meetings and finalist discussions.
• Deliver persuasive presentations communicating value and differentiation.
• Navigate complex buying groups across HR, benefits, finance, IT, procurement, and legal.

Skills

Enterprise sales

C-suite talks

Strategic selling

Long cycles

Negotiations

Solution design

Cross-functional

Education

Bachelor’s degree or equivalent

Job description

Jobgether is seeking a strategic Sales VP – Enterprise to lead the full enterprise sales cycle in the United States, targeting large employers with 35,000+ eligible employees. You will build trusted relationships with CHROs, CFOs, benefits leaders, and procurement teams, and collaborate with product, technology, legal, and implementation groups to tailor solutions.

This role emphasizes consultative selling, long, multi-stakeholder buying cycles, RFP processes, pricing negotiations, and contract