Job Description: Director of Customer Success

About benefitbay

Benefitbay is building the future of employee benefits.

We’re a broker-first, SaaS-driven ICHRA platform redefining how employers offer health benefits—moving the market away from opaque, one-size-fits-all group plans and toward a transparent, defined-contribution model that puts choice back in the hands of employees.

Our platform enables employers to transition to Individual Coverage Health Reimbursement Arrangements (ICHRA) with confidence, while giving employees the freedom to choose the coverage that fits their lives. At the same time, we empower brokers with modern tools that enhance—not replace—their role as trusted advisors.

What sets Benefitbay apart is our end-to-end approach: carrier-agnostic quoting and enrollment, built-in compliance intelligence, and fully integrated banking and reimbursement workflows—all designed to remove friction, increase transparency, and restore trust to the benefits experience.

We’re a growing team of builders, operators, and industry experts tackling one of the most complex and outdated systems in the U.S. If you’re excited by meaningful problems, real ownership, and the opportunity to help reshape healthcare benefits at scale, you’ll find that work—and your people—at Benefitbay.

About the Role

As Director of Customer Success, you will lead and scale the team responsible for delivering the Benefitbay brand promise across the full ICHRA lifecycle—from initial onboarding through long-term adoption, renewal, and growth. You will own the end-to-end customer experience, ensuring brokers, employers, and employees receive a consistent, high-impact experience as they transition to and operate on the Benefitbay ICHRA platform.

This role is equal parts people leadership, cross-functional partnership, and operational excellence. You will build and develop a high-performing team of Customer Success Managers who guide multiple audiences through one of the most complex changes in employee benefits with clarity, confidence, and care.

You will work closely with leaders across Sales, Compliance Success, Education Support, Product, and Operations to ensure expectations set during the sales process translate into successful, durable customer outcomes. You will help close the loop between pre-sale commitments and post-sale delivery—creating a seamless handoff, shared accountability, and a unified customer narrative.

A core measure of success for this role is customer retention and churn reduction. You will define and operationalize proactive success motions that drive adoption, accelerate time-to-value, and reduce churn across brokers, employers, and employee populations. Using data and insights, you will identify risk early, recommend improvements to process and product, and provide clear, actionable guidance to senior leadership on how to strengthen long-term customer outcomes.

The ideal candidate is energized by building teams that win together. You take pride in developing talent, creating accountability through clear processes and metrics, and using data to continuously improve performance. Your ability to balance empathy with execution—and strategy with delivery—will directly shape Benefitbay’s reputation as a trusted leader in ICHRA.

In this role, you will own success across key customer moments, including:

• Agency onboarding and activation
• Broker training and enablement
• Sales-to-Success handoff and expectation alignment
• User journey and experience mapping
• Customer milestones, retention, and churn reduction
• Employer onboarding and implementation
• Employer enrollment strategy and execution
• Post-enrollment success, renewal readiness, and expansion

This is a leadership role for someone who wants to build the team that keeps customers successful, loyal, and growing—while changing the world of employee benefits in the process.

Responsibilities

• Build, lead, and scale an industry-leading Customer Success organization that consistently delivers the Benefitbay brand promise across brokers, employers, and employees.
• Own customer retention and churn reduction by designing proactive success motions that drive adoption, accelerate time-to-value, and mitigate risk across the full customer lifecycle.
• Develop and execute training, enablement, and engagement strategies that support SaaS adoption and long-term success for brokers, employers, and internal teams.

• Partner closely with Sales to ensure strong sales-to-success handoffs, aligned expectations, and feedback loops that strengthen pipeline quality and long-term customer outcomes.
• Establish and report on Customer Success KPIs (including churn, retention, onboarding effectiveness, and enrollment outcomes), providing clear insights and recommendations to senior leadership.
• Serve as a voice of the customer, gathering insights through direct engagement and translating feedback into actionable input for Product, Sales, and Marketing teams.
• Guide customers through product evolution, ensuring brokers and employers understand and realize value from new features, enhancements, and capabilities.
• Support and influence Benefitbay’s go-to-market strategy by providing broker and employer insights that inform positioning, messaging, and growth opportunities.
• Create a culture of accountability, resilience, and continuous improvement, leading with composure as customer needs evolve and business priorities shift.
• Contribute as a senior leader in a growing organization, stepping in where needed to help the business scale effectively and sustainably.

What we are looking for

• 5+ years of progressive leadership experience in Customer Success or a related SaaS function, with demonstrated ownership of retention, team performance, and customer outcomes.
• A proven ability to build, develop, and retain high-performing teams, creating clarity, accountability, and growth paths for Success professionals.
• Strong business and operational judgment, with the ability to navigate ambiguity, design process where none exists, and find solutions when there is no obvious playbook.
• Exceptional communication skills, both written and verbal, with the ability to influence across Sales, Product, Support, and Executive Leadership.
• Comfort operating in a fast-paced, scaling SaaS environment, adapting quickly as priorities, processes, and customer needs evolve.
• High level of technical fluency, including experience with CRM and communication platforms (e.g., HubSpot, Aircall) and the ability to quickly adopt new tools and workflows.
• Customer-obsessed and data-informed, using metrics, reporting, and feedback to drive decisions and continuous improvement.
• A growth mindset, with a genuine commitment to learning—viewing every challenge as an opportunity to improve the team, the product, and the customer experience.
• A strong sense of ownership and integrity, with a commitment to privacy, security, and trust in every customer interaction.
• Insurance or benefits domain experience is preferred, with the ability to obtain a Health & Life License within 60 days of hire if not already licensed.
• Bachelor’s degree plus equivalent practical experience in Customer Success, Operations, or a related field. Master's degree preferred.

Additional Requirements

• Up to 20% travel is required for this role
• Location – Kansas City MO (Hybrid Onsite)
• This role requires flexibility of working hours during peak enrollment periods and extensive investment in flexibility of working hours from November – February.