Head of Customer Success

Bask Health

2d•Remote

About The Position

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.

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.)

Nice To Haves

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.

Responsibilities

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