Director, Customer Success

Job Description

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 Degree.
• The ability to travel to clients about 5 business day per quarter.
• 8+ years of experience in Customer Success, Strategic Account Management, Consulting, or other customer-facing leadership roles.
• 3+ years of people management experience leading and developing high-performing customer-facing teams.
• A proven track record in managing and growing large-scale strategic enterprise accounts, ideally supporting customers with populations of 20,000+ lives.
• Experience in B2B SaaS, healthcare technology, benefits, or other highly consultative environments.
• Strong executive communication, relationship-building, and stakeholder management skills.
• Experience driving retention, expansion, customer adoption, and value realization initiatives.
• Strong analytical and operational skills with the ability to leverage customer data and business metrics to guide decision-making.
• Demonstrated success operating cross-functionally and influencing senior stakeholders.
• Comfort navigating fast-paced, high-growth environments where strategy and execution happen simultaneously.

Nice to Have ⭐

While not required, we would be especially excited if you bring:

• Experience supporting enterprise HR, benefits, healthcare, or people-focused customer organizations.
• Experience working within fertility, digital health, healthcare benefits, or broader health tech industries.
• Experience scaling or transforming Customer Success organizations within high-growth companies.
• Familiarity with customer success platforms, health scoring methodologies, and enterprise renewal strategies.

Why This Role Matters 🧡

This role sits at the center of Carrot’s customer experience and long-term growth strategy.

As Director, Customer Success, you will directly influence how Carrot partners with some of the world’s most recognized employers and organizations. Your leadership will help ensure customers achieve meaningful outcomes while enabling Carrot to continue expanding access to fertility and family-forming care globally.

You will have the opportunity to shape strategy, develop talent, strengthen customer partnerships, and help define the future of Strategic Customer Success at Carrot.

Interview Process 🤝

We believe in a thoughtful and transparent interview process designed to create alignment for both candidates and our team.

For this role, candidates can expect:

1. Recruiter Screen — 30 minutes
2. Hiring Manager Interview — 30 minutes
3. HR Interview— 30 minutes
4. Panel Interview— 30 minutes
5. Hiring Manager Wrap-Up — 15 minutes

Throughout the process, we will share additional context about the team, business priorities, customer landscape, and what success looks like in this role.

Why Candidates Join Carrot 🌍

Carrot offers the opportunity to do meaningful work in service of a deeply human mission.

Highlights include:

• A mission-driven company focused on expanding access to fertility and family-forming care globally.
• A high-growth environment where leaders are empowered to shape strategy and drive impact.
• Competitive compensation, equity, and comprehensive benefits.
• Flexible Time Off and a culture that actively encourages employees to recharge.
• Comprehensive parental leave and family-forming benefits.
• A collaborative, inclusive, and values-driven culture.
• The opportunity to work alongside passionate, thoughtful teammates committed to improving healthcare outcomes worldwide.

Compensation 💰

Carrot offers a holistic Total Rewards package designed to support employees in all aspects of life inside and outside of work, including health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and more.

The starting base salary for this position will range from $155,000- $180,000, plus a variable component. Actual compensation may vary depending on confirmed job-related skills, experience, and location.

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