Head of Customer Success

Bask is the best telehealth platform on the market. Our mission is to empower entrepreneurs and businesses to launch a DTC telemedicine company quickly and easily, abstracting away the complexities of the industry into an easy-to-use platform. With hundreds of features to meet the unique needs of telehealth, we put all the tools in our customers' hands for success. We are a rapidly growing startup, and we work with care and intention to create a high-performance company with the following in mind:

Speed Wins. Make decisions, move quickly, and know that if things go wrong, it's okay for you and the company.

Intuition, Then Data. We're a data-driven company. We start with our instincts and then use data to validate our decisions and improve

Miles, Not Inches. Thinking small is a self-fulfilling prophecy. Favor bold ideas over incremental changes

Customer-Obsession. We are obsessed with helping all our customers launch multi-billion-dollar companies with ease. We accomplish this by knowing our customers incredibly well and finding ways to make their businesses better.

Ownership & Accountability, together. We embody a culture of extreme ownership, accountability, and teamwork. We count on every team member to take responsibility for their work, embrace a proactive mindset to overcome challenges, and work together to achieve our collective success

About the Role

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
• We're Looking For A builder and a leader who is passionate about the customer experience and equally excited about building the team and systems that deliver it at scale. You think outside the box, excel at creative problem-solving, and are comfortable taking on projects you have never done before. You are a people person — empathetic, self-aware, low ego, and extremely positive — and you're comfortable rolling up your sleeves in a fast-paced startup where no task is too small and no task is too tall. You're an exceptional written and spoken communicator who treats AI as a real collaborator.

Requirements

• 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.)