Enterprise CS Manager - Flexible PTO, WFH Setup

Benepass, Inc.; United States; Hybrid; USD 125,000 - 145,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

WFH setup

Learning & Development benefit

Cell phone + internet stipend

Wellness stipend

Co-working & commuting benefit

Onsite team events

Flexible PTO

Job summary

Benepass, Inc. is seeking an Enterprise Customer Success Manager to own and grow a portfolio of 15–20 high‑value enterprise accounts. You will report to the Head of Customer Operations and collaborate with product, sales, engineering, and support to maximize customer value and retention.

You will build trusted executive relationships, develop success plans tied to business outcomes, and drive adoption and expansion across a strategic book of business.

Qualifications

• 5+ years of experience in customer success or account management in SaaS, fintech, healthcare, or the Benefits space.
• Direct experience with enterprise accounts and multi-stakeholder environments.
• Proven track record in retention and expansion within enterprise portfolios.

Responsibilities

• Own a portfolio of 15–20 high-value enterprise accounts through all stages of the customer lifecycle.
• Build multi-threaded relationships across customer organizations and drive adoption.
• Develop and execute account and renewal plans in partnership with Sales.
• Monitor health and renewal risk; lead mitigation for at‑risk accounts.
• Serve as voice of the customer to Product and Engineering.
• Create scalable enterprise CS playbooks and executive review content.

Skills

Enterprise account mgmt

SaaS experience

Relationship building

Executive communication

Cross-functional collaboration

Customer success strategy

Job description

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 Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures. To date, the company has raised approximately $75 million in equity capital.

Articles

• Founder Story - Jaclyn Chen

• Benepass Raises $40M Series B

Candidate Resources

• Benepass | Candidate Resource Page

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

TEAM & ROLE

As an Enterprise Customer Success Manager, you will own relationships with 15–20 high-value enterprise accounts, reporting directly to our Head of Customer Operations, Aileen Palmer. You will be responsible for driving customer outcomes, retention, expansion, and executive alignment across a strategic book of business.

This role involves building trusted relationships with executive sponsors and day-to-day administrators, developing success plans tied to business outcomes, and ensuring customers derive maximum value from our platform. You will lead strategic reviews, coordinate cross-functional resources, and identify opportunities for adoption, retention, and expansion in partnership with product, sales, engineering, support, and strategic alliances teams.

Currently, our Customer Success team is composed of:

• 1 Senior Manager, Customer Success

• 1 Senior Customer Success Enablement Manager

• 10 Customer Success Managers

It’s an exciting time to join our Customer Success team as we are expanding across all departments. This is a fantastic opportunity to shape and influence enterprise customer success processes while working with an innovative team. If you thrive in a fast-paced environment and have experience managing complex enterprise accounts, we’d love to hear from you!

WHAT YOU'LL DO AT BENEPASS

• Own a portfolio of 15–20 high-value enterprise accounts through all stages of the customer lifecycle, from onboarding to renewal and expansion

• Build multi-threaded relationships across customer organizations, including executive sponsors, People/HR, Finance, and administrators, and drive adoption through strategic enablement and best-practice guidance

• Develop and execute account plans, success plans, and renewal and expansion strategies in close partnership with Sales

• Monitor customer health, renewal risk, and value realization; proactively lead mitigation plans for at-risk accounts

• Serve as the voice of the enterprise customer by synthesizing feedback, business needs, and market insights for Product and Engineering

• Create and iterate on repeatable enterprise Customer Success playbooks, executive business review content, and internal processes that scale

ABOUT YOU

• You are a strategic, consultative partner who builds credibility with executive stakeholders and customer champions

• You're highly organized and able to manage 15–20 complex accounts simultaneously while delivering proactive, personalized service

• You're a clear communicator who can translate product capabilities, data, and customer goals into measurable business outcomes

• You're commercially minded, adaptable, and comfortable navigating ambiguity in a fast-paced startup environment

REQUIREMENTS

• 5+ years of experience in customer success or account management in SaaS, fintech, healthcare, or the Benefits space; enterprise experience strongly preferred.

• Direct experience working in the Benefits space and/or with complex, multi-stakeholder enterprise customers

• Proven success in quota driven roles, with a focus on retention and expansion

• Proven track record of managing and growing high-value enterprise accounts, including renewals, executive engagement, and expansion

• Demonstrated ability to analyze customer data and business insights to shape account strategy and influence stakeholder decision-making

• Ability to engage customer teams at varying levels of technical and non-technical depth, from end users and administrators through C-level stakeholders

• Experience orchestrating cross-functional teams and communicating customer needs, risks, and opportunities to Sales, Marketing, Product, and Engineering.

BONUS SKILLS

• Experience with enterprise account planning, executive business reviews, and value-based selling

COMPENSATION

Base Salary: $125,000 to $145,000 + variable + equity

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 (one time)

  • $500/year Learning & Development Benefit

  • $150/month cell phone + internet

  • $100/month Wellness

  • $100/month Co-working and Commuter Benefit

• We offer several team onsites a year

• Flexible PTO

At Benepass, we are working towards reimagining 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.