About Us

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.

Our Mission

Helping companies reimagine how companies take care of their people.

Our Investors

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.

Articles

• Founder Story - Jaclyn Chen

• Benepass Raises $20M

Candidate Resources

• Benepass | Candidate Resource Page

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

Position Overview

We’re looking for a Mid-Market Sales Manager to lead and develop a team of Account Executives selling to employers with under 5,000 employees. This leader will play a pivotal role in shaping the growth of our mid-market segment, refining sales strategy, coaching high-performing sellers, and helping the team consistently exceed revenue goals.

You’ll report to the Head of Sales and work closely with our GTM, Enablement, and Marketing teams to drive predictable growth in a fast-moving, collaborative environment.

Key Responsibilities

• Lead, coach, and scale a team of Mid-Market Account Executives focused on selling Benepass to HR, Finance, and Benefits leaders.

• Support your team throughout complex sales cycles — from discovery and ROI analysis to negotiation and close.

• Monitor and manage team performance through pipeline reviews, forecast accuracy, and activity tracking.

• Deliver consistent results against monthly and quarterly revenue targets.

• Partner with Enablement and Marketing to refine messaging, improve conversion rates, and shorten deal cycles.

• Identify process improvements to increase team efficiency, deal velocity, and win rates.

• Hire, onboard, and develop top-performing Account Executives, creating a culture of accountability and excellence.

• Collaborate cross-functionally with Customer Success and Product to ensure a seamless customer experience from sale to launch.

What You’ll Bring

• 3–5+ years of experience managing a high-performing SaaS or benefits-tech sales team.

• Proven success as an individual contributor in closing mid-market or enterprise deals.

• Strong forecasting and pipeline management skills.

• Exceptional coaching ability, you know how to elevate talent and drive consistency.

• Experience selling to HR, Finance, or Total Rewards leaders (benefits, HRIS, HCM, or fintech experience a plus).

• High curiosity, adaptability, and desire to thrive in a rapidly scaling organization.

• Strong communication and collaboration skills, you’re as comfortable on a prospect call as in an executive strategy meeting.

Why Benepass

• Mission-driven team changing how companies think about benefits.

• High growth trajectory with a collaborative, values-driven culture.

• Competitive compensation package including base, variable, and equity.

• Fully remote with opportunities for team off-sites and connection.

• Comprehensive health benefits, flexible time off, and access to your own Benepass account.

Compensation

The estimated on-target earnings (OTE) for this role are $250,000 – $280,000 USD per year, depending on experience and location.

Includes base salary + variable + equity.

#LI-Remote

Range(s) is subject to change. Benepass takes a number of factors into account when determining individual starting pay, including market comparables, interview performance, peer compensation, and years of experience.

What We Offer

• 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.