Director, Customer Success

About this role

About Carrot:

Carrot is the leading global fertility and family care platform, built on intelligent care orchestration: the right clinical guidance, at the right moment, in the context of each member’s life. More than a thousand multinational employers, health plans, and health systems trust Carrot to support millions of members across 195 countries – from pre-pregnancy through menopause and major life moments in between. Carrot's comprehensive clinical program delivers industry-leading cost savings for plan sponsors and award-winning experiences and improved outcomes for millions of people worldwide.

Carrot is widely regarded as a defining force in healthcare innovation as a recipient of several top-tier awards, including Fast Company's 'Most Innovative Companies' and CNBC's '100 Barrier Breaking Startups'. The company is regularly cited by leading global outlets — including The Economist, Bloomberg, The Wall Street Journal, NPR, ABC News, and Harvard Business Review — as a leading voice on digital health, the future of work, and family health. Learn more at get-carrot.com.

The Opportunity 🚀

Carrot is seeking a Director, Customer Success to lead and evolve our Strategic Customer Success function—supporting Carrot’s largest and most complex enterprise customers with populations of 20,000+ lives.

This is a highly strategic leadership role focused on driving long-term customer value, retention, growth, and engagement across Carrot’s most important customer relationships. You will shape the vision, operating model, and execution strategy for the Strategic Customer Success segment while partnering closely with leaders across Product, Sales, Marketing, Operations, and Executive Leadership.

As a senior leader within Customer Success, you will help define how Carrot delivers measurable business outcomes for enterprise customers while influencing the future of our customer experience, product roadmap, and go-to-market strategy.

The ideal leader brings a strong customer-centric mindset, operational rigor, executive presence, and a passion for developing high-performing teams in a fast-paced, mission-driven environment.

What You’ll Own 💼

In this role, you will:

• Lead, coach, and develop a team of Senior Customer Success Executives and Customer Success Executives responsible for Carrot’s most strategic enterprise accounts.

• Define and execute a customer success strategy focused on retention, expansion, adoption, and long-term customer health.

• Build strong executive-level relationships with customer stakeholders and serve as an executive sponsor for key strategic accounts.

• Drive customer engagement strategies that increase value realization, member adoption, and measurable business impact.

• Partner cross-functionally with Product, Sales, Marketing, Operations, and other internal stakeholders to ensure a seamless and high-impact customer experience.

• Leverage customer health metrics, renewal data, adoption insights, and feedback trends to proactively identify risks and growth opportunities.

• Establish scalable operational processes and best practices across strategic account management, QBRs, renewals, and customer planning.

• Influence product strategy and innovation by representing the voice of the customer internally.

• Partner with Customer Success leadership on organizational planning, segmentation strategy, team structure, and long-term scaling initiatives.

• Foster a culture of accountability, collaboration, continuous improvement, and customer obsession across the team.

What Success Looks Like 📈

In your first 12–18 months, you will have:

• Strengthened retention and customer health across Carrot’s strategic customer portfolio.

• Improved executive-level customer engagement and positioned Carrot as a trusted long-term partner.

• Built scalable Customer Success operating rhythms and processes that improve consistency, visibility, and execution.

• Increased customer adoption, engagement, and expansion opportunities across key accounts.

• Developed and elevated a high-performing Customer Success team through coaching, mentorship, and clear accountability.

• Established data-driven approaches to identifying churn risks and growth opportunities.

• Strengthened cross-functional alignment between Customer Success, Sales, Product, and Operations.

• Helped shape the future strategy and growth of Carrot’s Strategic Customer Success organization.

About You ✨

You are a strategic customer success leader who knows how to balance customer outcomes, team leadership, and operational excellence. You bring executive presence, strong business judgment, and the ability to lead through growth and complexity.

You likely have:

• A Bachelor's…