Enterprise Sales Director, Benepass

• You’ll thrive here if you’re passionate about improving the employee experience, navigating benefits technology, and closing deals that transform how companies support their people
• 3–6 years of B2B SaaS or benefits technology sales experience, ideally within health, wellness, or total rewards
• Proven track record of consistently meeting or exceeding quota in a full-cycle AE role
• Experience selling to HR, Benefits, or Finance executives
• Strong discovery, presentation, and objection-handling skills
• Familiarity with benefits administration, LSAs, FSAs, HSAs, or wellness platforms a plus
• Consultative selling mindset—able to translate complex benefits concepts into simple, value-based conversations
• Self-starter who thrives in a fast-paced, mission-driven environment
• Comfortable operating in Salesforce and using sales engagement tools (e.g., Outreach, Gong, LinkedIn Sales Navigator)

Desirable

• We’re looking for an ambitious and consultative Sales Director to drive new business with medium to large employers (5k - 30k employees)
• This role blends strategic selling with solution-oriented problem solving. You’ll educate benefits leaders on how Benepass can modernize their benefits programs and streamline pre-tax spending account complexity
• Own the full sales cycle from prospecting to close for large employers
• Build and manage a robust pipeline through outbound efforts, referrals, and partner channels
• Conduct discovery with benefit and total rewards leaders to identify pain points and align Benepass solutions to business goals
• Deliver compelling product demos and ROI presentations that articulate Benepass’ differentiated value
• Partner cross-functionally with Solutions Consulting, Marketing, and Partnerships to accelerate deal velocity and improve win rates
• Navigate multiple stakeholders (benefits, finance, procurement, IT) within complex buying groups
• Maintain accurate forecasting and pipeline hygiene in Salesforce
• Meet and exceed quarterly and annual revenue targets
• Represent Benepass at industry events, conferences, and webinars to build relationships and market presence