Strategic Account Executive

Responsibilities

• Own the full lifecycle of 25–50 named Fortune 500 accounts including prospecting, closing, onboarding, expansion, and renewal
• Build and maintain strategic account plans for both prospects and existing clients
• Run complex multi-stakeholder enterprise sales cycles with HR, Benefits, and Finance leaders
• Partner with the Implementation team to ensure clean onboarding
• Drive employee awareness and adoption during enrollment windows
• Identify and execute upsell and cross-sell opportunities
• Lead renewal negotiations and build business cases for continued investment
• Forecast accurately across new bookings, enrollment health, and renewal pipelines
• Collaborate cross-functionally with Marketing, Product, and Finance

Requirements

• 7+ years of B2B/SaaS sales experience with end-to-end account ownership
• Demonstrated success selling to Fortune 500 HR and Benefits leaders
• Experience working with brokers and consultants in regulated environments
• Proven track record of defending and growing revenue at renewal
• Strong executive presence for operating with VP/C-level stakeholders
• Experience with CRM and account-planning tools like Salesforce
• Top performance recognition such as President's Club

Benefits

• Comprehensive health, vision, and dental coverage
• HSA/FSA
• 401(k) retirement planning with employer matching
• Unlimited paid time off
• Annual company holidays and recharge days
• 12 weeks parental leave
• Company paid Wagmo pet wellness and insurance plans
• Regular company-wide events and team gatherings