[Hiring] Head of Customer Success @Bask Health

Role Description

As Head of Customer Success, you'll own the entire post-sale customer experience at Bask — from onboarding and launch through retention, expansion, and renewal. You'll lead and grow the Customer Success team, set the strategy and operating model for how we serve customers, and be accountable for the metrics that matter most: retention, expansion, and customer health. You'll report to leadership and act as the voice of the customer across product, engineering, sales, and operations.

Customer Success at Bask Health is AI-first and customer-obsessed. Work starts in an LLM to clarify intent and context, moves into research and execution, is validated with real patients and partners, and is continuously refined as we learn. AI and self-serve research are default parts of the workflow, not side experiments. We're looking for a leader who builds a team in that image.

What You'll Do

• Lead and build the team
• Hire, manage, coach, and develop a high-performing team of Customer Success Managers, setting clear expectations and holding the bar high
• Design the team structure, account segmentation, and coverage model as we scale (e.g., enterprise vs. growth accounts, pooled vs. dedicated support)
• Create a culture of ownership where every CSM treats their accounts like their own business
• Own the strategy and the numbers
• Own net revenue retention, gross retention, churn, and expansion targets for the customer base
• Define and track customer health scores, engagement metrics, and leading indicators of risk and growth
• Report on customer outcomes, trends, and opportunities to the executive team, with clear recommendations
• Build the operating system
• Build scalable playbooks for onboarding, launch, adoption, QBRs, renewals, upsell, and escalations
• Lead the AI-native operating model for CS: develop, document, and share prompts, workflows, and automations that make the team faster and better — and make sure customers understand what Bask's platform is doing on their behalf
• Select and implement CS tooling and processes, and keep customer data clean and actionable
• Stay close to customers
• Serve as executive sponsor for key and enterprise accounts, and personally step in on high-stakes escalations
• Partner with customers to develop engagement initiatives that drive adoption and support the unique needs of their patients
• Deliver program demos and strategic reviews, provide insightful technical answers, and recommend creative ways to get the most out of the Bask platform
• Validate approaches with real customers, providers, and partners, and use what you learn to improve how we serve them before issues become patterns
• Be the voice of the customer
• Partner with Product and Engineering to prioritize roadmap needs based on customer feedback and data
• Work with Sales on handoffs, account planning, and expansion opportunities
• Collaborate with Operations, Pharmacy, and Support to resolve systemic issues affecting customers

Qualifications

• 10+ years of experience in Customer Success, Account Management, or Client Services, ideally at a SaaS or platform company
• 4+ years of experience leading Customer Success teams, including hiring, coaching, and performance management
• Experience in e-commerce
• Experience with large- to enterprise-sized customer book of business
• Creative problem solver with a determination to succeed
• Independent and motivated, with the wisdom to seek help where needed
• An entrepreneur
• Highly articulate, ability to communicate effectively both when speaking and writing
• Highly organized, with the ability to juggle multiple projects in a fast-paced environment
• Comfortable collaborating with different teams (product, sales, marketing, etc.)

Requirements

• Remote Worldwide (Working Hours East Coast Time 9am to 6pm)