Senior Enterprise Sales VP — Benefits & HR Tech

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

Benefits offered by this job

Remote-friendly work environment

Health coverage

Retirement savings plan

Professional development

Job summary

OpenKrill is seeking a Sales VP - Enterprise based in the United States to lead the full sales cycle for large employers and partnerships in the employee benefits and HR technology space.

The role requires 10+ years in enterprise sales, strong relationships with C-suite and HR leaders, and an ability to translate complex requirements into differentiated solutions. Remote-friendly, with standard business hours and a focus on strategic growth.

Qualifications

• 10+ years in enterprise or strategic sales.
• Experience selling benefits administration, HR technology, insurance, or SaaS to large enterprises.
• Direct experience selling to employers with 35,000+ employees.
• Proven ability to manage long, complex sales cycles with multiple stakeholders.
• Experience presenting to CHROs, CFOs, benefits executives, IT leaders, procurement, and other C-suite stakeholders.
• Familiarity with benefits administration, enrollment tech, implementations, data integrations, and enterprise service delivery.
• Proven experience leading complex RFPs, finalist presentations, pricing discussions, and contract negotiations.
• Bachelor’s degree or equivalent professional experience.

Responsibilities

• Represent enterprise benefits administration technology and services to large employers.
• Develop and execute sales strategies to penetrate enterprise markets and achieve revenue growth.
• Build relationships with senior executives, consultants, brokers, and industry partners.
• Identify prospects, cultivate relationships, and maintain a qualified pipeline of large opportunities.
• Own the full enterprise sales cycle from discovery to closing.
• Coordinate cross-functional teams to develop proposals and advance opportunities.
• Lead internal strategy sessions for customer meetings and executive discussions.
• Deliver persuasive presentations that communicate capabilities and value.
• Navigate complex buying groups across HR, finance, IT, procurement, and legal.
• Negotiate pricing, service models, and contractual terms.
• Position a broad portfolio of benefits tech, admin, and services.
• Strengthen relationships with industry influencers and maintain conference presence.
• Maintain accurate sales pipeline data and provide status updates.
• Partner with implementation teams to ensure smooth transitions.

Skills

Enterprise sales

Strategic selling

C-suite presentations

RFPs & negotiations

Stakeholder management

HR technology

Benefits administration

SaaS sales

Cross-functional collaboration

Education

Bachelor's degree

Job description

OpenKrill is seeking a Sales VP - Enterprise based in the United States to lead the full sales cycle for large employers and partnerships in the employee benefits and HR technology space.

The role requires 10+ years in enterprise sales, strong relationships with C-suite and HR leaders, and an ability to translate complex requirements into differentiated solutions. Remote-friendly, with standard business hours and a focus on strategic growth.