Enterprise Sales Director

At Benepass we're making benefits easy. We believe people are the most important asset to any company. Traditional one-size-fits-all benefits packages no longer cut it in today's hybrid and remote-first environment. With Benepass, companies can tailor their benefits to the unique needs of their workforce.

Through our easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track the benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories. Every employee has their own individual definition of wellness and needs different things to help them be their most productive, fulfilled self.

Helping companies reimagine how companies take care of their people.

We are backed by leading investors, including Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised $35 million of equity capital.

• Founder Story - Jaclyn Chen

• Benepass Raises $20M

• Benepass | Candidate Resource Page

• Benepass Listed on Inc. Magazine's Best Workplaces of 2023

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.

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.

• 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.

• 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).

• Prior experience with companies like Garner Health, Health Equity, Sequoia, Gusto, or Betterment at Work.

• Understanding of HRIS/payroll integrations and data exchange processes.

• Exposure to selling through benefits brokers or consultants.

• Training and Development: Comprehensive onboarding and ongoing training programs to support your professional growth.

• Career Advancement: Clear pathways for career progression within the sales department and beyond.

• Supportive Environment: A collaborative and inclusive work culture that values diversity and encourages innovation.

• Competitive Compensation: A base salary with performance-based incentives and benefits package.

• Base: $150,000 - $180,000 + Variable Compensation + Equity

• 95% coverage of medical, dental, and vision

• Fantastic benefits (of course 😃), including:

  • $250 WFH setup

  • $150/month cell phone + internet

  • $100/month Wellness

• We offer several team onsites a year

• Flexible PTO

At Benepass, we are working towards reimaging how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal-opportunity employer.