Act as the "CEO" of your territory, identifying high-potential prospects and maintaining a robust, healthy sales pipeline.
Manage the end-to-end sales process from cold outreach and initial discovery to deal advancement and contract negotiation.
Execute high-volume, multi-channel prospecting strategies to build relationships and engage key decision-makers (VPs of HR, Benefits Directors) and Benefits Consultants.
Conduct deep discovery to understand your client’s challenges and pain points to tailor solutions that demonstrate clear ROI and clinical value.
Travel as needed (up to 40-50%) within the territory to lead in-person presentations, attend regional conferences, and build local broker relationships.
Maintain accurate records in Salesforce and provide leadership with accurate sales forecasts.

7+ years of successful B2B sales experience (Sales Executive), preferably within benefits, health-tech, or SaaS.
Proven history of exceeding annual quotas with complex sales cycles (6-12 months long).
Exceptional interpersonal, collaboration, and negotiation skills; the ability to simplify complex behavioral health concepts for diverse audiences (HR, Finance, and C-Suite).
Highly organized with the ability to manage multiple complex sales cycles at the same time.
A "bias for action"; you quickly recover from setbacks and modify strategies to fit changing market circumstances.

Comprehensive healthcare coverage (including medical, dental, vision, FSA/HSA, life and disability insurances)
Lyra for Lyrians; coaching and therapy services
Equity in the company through discretionary restricted stock units
Competitive time off with pay policies including vacation, sick days, and company holidays
Paid parental leave
401K retirement benefits
Monthly tech allowance
We like to spread joy throughout the year with well-being perks and activities, surprise swag, free food, regular community celebration…and more!

Sales Executive, Strategic – Midwest

Key skills