Vice President, Customer Success

VP, Customer Success & Retention

Location: Tampa

The Company

Healthcare benefits are one of the biggest investments companies make in their people — and one of the most underutilized.

Employers spend heavily on benefits their employees struggle to understand and use. When engagement drops, the value of the benefit is questioned, renewals get harder, and relationships are at risk.

The company sits at that intersection: making benefits simpler, more connected, and more valuable for employees, employers, and partners.

We’re looking for a VP of Customer Success & Retention to own the outcome that compounds everything else: net revenue retention.

This is a commercial leadership role for a builder: someone who can protect revenue, drive expansion, and evolve Customer Success into a scalable, AI-enabled growth engine.

The Opportunity

The company has built a strong foundation: an experienced Customer Success team, a growing data infrastructure, and early AI capabilities already improving how we operate.

Now we’re focused on the next stage: building a predictable retention and expansion engine that allows us to scale efficiently while delivering exceptional customer outcomes.

You’ll define what modern Customer Success looks like, combining strong operators, disciplined processes, better data, and AI-powered workflows to increase customer value.

The Role

As VP of Customer Success & Retention, you’ll own the strategy, execution, and results of our Customer Success organization.

You’ll lead the team responsible for retention, expansion, customer health, and the operating systems behind our customer lifecycle. You’ll know where revenue is being protected, where risk exists, and what actions will move the business forward.

This role sits at the intersection of customers, revenue, and operations. You’ll partner closely with Sales, Broker Partnerships, Marketing, RevOps, Data, Product, and Legal.

What You'll Do

• Own retention and expansion outcomes: Own net revenue retention, gross retention, renewals, and expansion strategy. Build the forecasting discipline, operating cadence, and customer health model needed to identify risks early and drive action.
• Build a scalable Customer Success engine: Create the processes, systems, and team structure needed to support growth while improving customer outcomes.
• Increase customer value and product adoption: Develop strategies that improve engagement, demonstrate ROI, and turn successful customers into long-term growth partners.
• Lead AI-enabled transformation: Use AI, automation, and better customer intelligence to improve how the team operates — reducing manual work, increasing insight, and allowing the team to focus on the moments that require judgment.
• Create operating rigor through data: Establish Salesforce as the source of truth for customer health, forecasting, renewals, and expansion opportunities.
• Be the executive voice of the customer: Own strategic relationships, executive business reviews, escalations, and customer feedback loops that influence the broader company.
• Build and develop the team: Lead a team of CS leaders and CSMs, raise the commercial maturity of the organization, and build the next generation of Customer Success talent.

What We're Looking For

• 8+ years in Customer Success, account management, or commercial retention roles with people management experience
• Proven ownership of retention, expansion, or revenue outcomes in a B2B environment
• Commercial mindset with the ability to connect customer activities to business results
• Experience building teams, processes, and operating rhythms in a high-growth environment
• Strong analytical skills and comfort using data to make decisions
• Ability to influence cross-functional partners across Sales, Product, Marketing, and Operations
• Executive presence with customers, partners, and internal leadership
• Excitement about using AI and technology to reinvent how Customer Success operates
• Healthcare, benefits, or SaaS experience preferred

This Role Is Not For Everyone

This is not a steady-state Customer Success leadership role.

You’ll be building while operating. That includes improving systems, creating new processes, shaping how the function evolves and everything in between.

If you’re excited by owning a number, building a team, and creating the next generation of Customer Success in an AI-native company, this is an opportunity to make a significant impact.

Reporting & Team

This role reports to the Chief Growth Officer and leads the Customer Success organization.