Head of Customer Growth & Retention

About Bask Health

Bask Health is a software platform that enables entrepreneurs, doctors, and healthcare businesses to launch, manage, and grow direct-to-consumer telehealth businesses.

Our platform brings together patient experiences, clinical workflows, pharmacy operations, and commerce tools in one place.

We're an entrepreneurial, product-focused team that values ownership, technical excellence, and building software that solves real problems. Our teams work closely across product, engineering, customer success, sales, and company leadership to bring new capabilities to market and continuously improve the platform.

At Bask, customer growth and retention are built on helping businesses succeed with our software over time. We value people who understand what drives customer loyalty, recognize opportunities for growth, and build strong teams and processes that support lasting customer relationships.

About the Role

We're looking for a Head of Customer Growth & Retention to lead Bask Health's post-sale customer growth strategy, strengthen customer retention, and develop scalable processes for expanding existing customer relationships.

This role combines customer success leadership, commercial strategy, account management, and operational execution.

You'll be responsible for building a customer success function that helps customers achieve value from Bask Health while supporting strong retention and sustainable recurring-revenue growth.

Our customers include entrepreneurs, e-commerce operators, online business owners, and healthcare businesses using Bask Health to launch, manage, and grow direct-to-consumer telehealth services.

You'll bring a strong understanding of e-commerce businesses, merchant operations, and the challenges entrepreneurs face when building and scaling online businesses.

You'll develop a customer growth and retention strategy that aligns customer needs with Bask Health's broader business objectives.

You'll define how the team approaches customer onboarding, adoption, engagement, renewals, retention, and account expansion.

You'll establish clear processes for identifying customers who are at risk of leaving and developing appropriate retention strategies.

You'll help the team recognize early warning signs of declining engagement, reduced product adoption, or customer dissatisfaction.

You'll develop customer health monitoring practices that provide visibility into retention risks and opportunities.

You'll work with customer success managers to ensure customer goals, account priorities, and growth opportunities are clearly documented.

You'll establish expectations for proactive account management and consistent customer communication.

You'll lead, coach, and develop customer success team members within the approved organizational structure.

You'll help team members strengthen their ability to manage customer relationships, navigate renewal conversations, and identify appropriate expansion opportunities.

You'll build a team culture that values accountability, strong commercial judgment, and meaningful customer outcomes.

You'll work with leadership to establish customer segmentation and account coverage strategies.

You'll help determine how resources should be allocated across strategic accounts, growing merchants, and smaller businesses.

You'll develop performance metrics and reporting practices for customer growth and retention.

You'll monitor relevant indicators such as customer churn, gross revenue retention, net revenue retention, renewals, expansion, and product adoption.

You'll establish processes for analyzing why customers leave and identifying recurring causes of churn.

You'll use customer feedback and account performance data to recommend improvements.

You'll create proactive strategies for strengthening relationships with customers who show signs of dissatisfaction.

You'll oversee important customer escalations that may affect retention or long-term account value.

You'll build relationships with strategic customer stakeholders, including founders, executives, and business owners.

You'll participate in high-priority customer conversations when leadership involvement can help resolve concerns or strengthen relationships.

You'll guide the team in conducting business reviews focused on customer goals, platform adoption, business performance, and opportunities for growth.

You'll work closely with sales leadership to coordinate renewal preparation and expansion opportunities.

You'll establish clear responsibilities between customer success and sales for identifying, qualifying, and pursuing expansion opportunities.

You'll help ensure commercial conversations are grounded in customer needs and supported platform capabilities.

You'll identify opportunities for customers to adopt additional features or expand their use of Bask Health when those capabilities support their business goals.

You'll collaborate with product and engineering teams to address recurring issues that affect customer satisfaction and retention.

You'll communicate customer feedback, product limitations, and adoption challenges to the appropriate internal teams.

You'll work with technical support and customer success engineering teams to address technical problems that create churn risk.

You'll help identify recurring implementation challenges that prevent customers from realizing value.

You'll support improvements to onboarding, customer education, and implementation handoffs.

You'll ensure the customer success team understands how Bask Health's capabilities support different merchant business models.

Our platform brings together merchant storefronts, patient questionnaires, checkout experiences, clinical workflows, pharmacy-related processes, and other business capabilities.

You'll help the team connect these capabilities to practical customer needs without promising unsupported functionality.

You'll establish clear processes for recognizing when customer requests require technical, clinical, pharmacy, or compliance expertise.

You'll coordinate with authorized teams when issues involve regulated healthcare activities.

You'll ensure customer-facing processes follow appropriate privacy, security, and information-handling requirements.

You'll develop scalable customer retention and expansion playbooks.

You'll evaluate customer success tools, workflows, and reporting systems to identify opportunities for improvement.

You'll create consistent processes for tracking renewals, retention risks, expansion opportunities, and customer commitments.

You'll collaborate with leadership on organizational planning, staffing needs, and team development.

You'll participate in hiring and evaluating customer success talent as needed.

You'll establish performance coaching and professional development practices that reinforce strong account management and commercial execution.

You'll help create effective collaboration between customer success, sales, product, engineering, and technical support teams.

You'll work directly with company leadership to communicate customer growth performance, retention trends, and emerging risks.

You'll provide recommendations for improving recurring-revenue performance through stronger post-sale customer engagement.

You'll balance customer advocacy with commercial priorities and operational realities.

You'll develop strategies that strengthen long-term customer relationships while supporting responsible revenue growth.

We're looking for a leader with substantial post-sale customer success experience, proven team management ability, and meaningful e-commerce experience.

You should understand how merchant-facing SaaS businesses operate and how customer retention and account expansion contribute to long-term company growth.

You'll need to be comfortable building processes, coaching teams, managing strategic accounts, and making data-informed commercial decisions.

Success in this role means improving customer retention, reducing preventable churn, increasing appropriate account expansion, and building a customer success organization that contributes directly to Bask Health's long-term growth.

What You'll Do

• Lead Bask Health's customer growth and retention strategy.
• Develop scalable processes for customer renewals, retention, and expansion.
• Establish customer health monitoring and churn-risk identification practices.
• Build proactive strategies to reduce preventable customer churn.
• Lead and coach customer success team members within the approved organization.
• Establish clear expectations for account ownership and commercial accountability.
• Develop customer segmentation and account coverage strategies.
• Monitor customer retention, churn, renewals, and expansion performance.
• Track gross revenue retention and net revenue retention where applicable.
• Establish customer growth and retention reporting practices.
• Analyze recurring causes of customer churn and recommend improvements.
• Identify opportunities to strengthen customer engagement and product adoption.
• Oversee strategic customer relationships and executive-level engagements.
• Guide customer success managers in conducting business reviews and renewal discussions.
• Support appropriate account expansion opportunities.
• Collaborate with sales on customer growth and expansion strategies.
• Establish clear handoffs between customer success and sales.
• Work with product and engineering on issues affecting retention.
• Coordinate with technical support and customer success engineering teams.
• Improve onboarding and implementation handoffs that affect long-term adoption.
• Develop customer retention and expansion playbooks.
• Establish consistent processes for documenting renewal risks and account opportunities.
• Build reporting that connects customer success activities to recurring-revenue performance.
• Oversee important customer escalations affecting account health.
• Coach team members on account management, commercial judgment, and customer communication.
• Support organizational planning and customer success hiring.
• Improve customer success tools, workflows, and documentation.
• Establish clear collaboration between customer success and other departments.
• Promote accountability for retention and customer growth outcomes.
• Ensure appropriate privacy, security, and information-handling practices.
• Escalate clinical, pharmacy, and compliance matters to authorized teams.
• Provide leadership with clear updates on customer growth, retention, and risks.
• Take ownership of the customer success function's retention and expansion effectiveness.

Requirements

• 10+ years of experience in customer success, account management, client services, or a closely related post-sale customer-facing function.
• At least 4 years of experience directly managing and developing customer success or account management teams.
• Demonstrated ownership of post-sale customer success strategy and operations.
• Recent, substantive experience working with e-commerce businesses, online merchants, or merchant-facing commerce software.
• Strong understanding of e-commerce business models, direct-to-consumer operations, and merchant needs.
• Experience developing customer retention and account growth strategies.
• Proven ability to lead customer onboarding, adoption, renewal, retention, and expansion initiatives.
• Experience creating processes for identifying and reducing customer churn.
• Demonstrated ability to coach, develop, and evaluate customer-facing employees.
• Experience establishing customer success performance metrics and reporting.
• Strong understanding of customer retention, churn, account health, and renewal performance.
• Familiarity with gross revenue retention, net revenue retention, and recurring-revenue metrics.
• Experience developing strategies for improving long-term customer engagement.
• Demonstrated experience supporting expansion opportunities within existing customer accounts.
• Strong commercial judgment and understanding of recurring-revenue SaaS businesses.
• Experience managing relationships with founders, executives, and senior customer stakeholders.
• Ability to lead strategic account reviews and renewal discussions.
• Experience handling complex customer escalations and retention risks.
• Experience collaborating with sales, product, engineering, and company leadership.
• Ability to translate customer feedback into operational and product recommendations.
• Experience building customer retention and account management playbooks.
• Strong written and verbal communication skills.
• Ability to present retention and account growth performance to leadership.
• Strong analytical thinking and data-driven decision-making skills.
• Experience managing multiple strategic priorities and competing demands.
• Strong organizational and operational planning skills.
• Ability to lead teams in a remote, cross-functional environment.
• Availability to collaborate during required U.S. Eastern Time working hours.
• Strong ownership mentality and accountability for customer and team outcomes.

Nice to Have

• Experience leading customer success or account growth at an e-commerce SaaS company.
• Experience managing customer success teams serving Shopify merchants.
• Familiarity with Shopify, BigCommerce, Klaviyo, Recharge, Gorgias, Yotpo, or similar commerce platforms.
• Experience supporting direct-to-consumer brands and online entrepreneurs.
• Personal experience building or operating an e-commerce business.
• Experience leading customer success for both SMB and strategic accounts.
• Experience managing enterprise customer relationships.
• Experience improving gross revenue retention and net revenue retention.
• Experience developing churn prediction and customer health scoring processes.
• Experience creating renewal forecasting and retention reporting.
• Experience designing account expansion and upsell processes.
• Experience collaborating with sales on expansion opportunities.
• Familiarity with Salesforce, HubSpot, Gainsight, ChurnZero, or similar platforms.
• Experience designing customer segmentation and account assignment models.
• Experience building customer success teams during periods of growth.
• Experience leading cross-functional retention initiatives.
• Experience developing customer lifecycle and engagement strategies.
• Experience improving technical onboarding and implementation handoffs.
• Familiarity with online storefront, checkout, and payment workflows.
• Experience supporting healthcare technology or telehealth businesses.
• Experience working directly with founders and senior company leadership.