VP of Customer Success

EnrollHere is seeking a strategic and customer-obsessed Vice President of Customer Success to lead and scale our post-sale customer experience. This is a high-impact leadership role for someone who thrives in a fast-paced environment and is equally comfortable rolling up their sleeves and thinking long-term.

As VP of Customer Success, you will be responsible for the full customer lifecycle—from onboarding through renewal and expansion. You’ll build and mentor a high-performing team while driving initiatives that improve retention, satisfaction, and long-term value. This role requires a deep understanding of SaaS metrics, customer lifecycle management, and operational execution.

Reporting directly to the CEO, you’ll work cross-functionally with Product, Engineering, Sales, and Marketing to ensure every customer interaction reflects our mission and delivers exceptional value. If you’re passionate about building customer-first organizations and want to shape the future of healthcare technology, we encourage you to apply.

Responsibilities

• Build, scale, and lead a high-performing Customer Success team (including onboarding, support, and account management)
• Define and execute the overall customer success strategy aligned with company OKRs
• Own the full post-sale customer journey: onboarding, adoption, engagement, renewal, and expansion
• Drive net revenue retention by improving time-to-value and customer outcomes
• Monitor account health metrics and proactively address churn risks
• Develop scalable processes for renewals, upsells, and cross-sells
• Partner cross-functionally with Product, Engineering, Marketing, and Sales to align on customer needs and priorities
• Implement and optimize Customer Success tools (e.g., Gainsight, HubSpot, Salesforce)
• Track KPIs such as NPS, CSAT, health scores, and churn rate; present insights to the executive team and board
• Foster a customer-centric culture across the organization

Requirements

10+ years of experience in Customer Success, Account Management, or Customer Experience roles

5+ years in a senior/executive leadership capacity, ideally in a high-growth SaaS environment

Proven track record of building and scaling Customer Success functions

Deep understanding of SaaS metrics and customer economics (e.g., NRR, CAC, LTV)

Experience managing enterprise customer relationships and retention strategies

Proficiency with CS platforms like Gainsight, HubSpot, Salesforce, or similar tools

Strong communicator and cross-functional collaborator with executive presence

Ability to thrive in a fast-moving, founder-led startup environment

Bachelor's degree in Business, Marketing, or a related field (MBA preferred)

Benefits

We believe in taking care of our team, which is why we offer a comprehensive benefits package that supports your health, wellness, and future:

• Medical: 4 United Healthcare medical plans (including an HSA option)
• Dental: 3 dental plans (Aetna and MetLife)
• Vision: 2 Aetna vision plans
• Wellness & Mental Health: 5 additional Medical Plus benefits, including telehealth support and an annual Talkspace subscription
• Ancillary Coverage: 4 ancillary plans and supplemental life insurance
• Retirement: 401(k) with a 4% match (after a 90-day exclusionary period)
• PTO & Flexibility: Generous PTO and remote work support
• Growth: Learning stipends and opportunities for professional development