Head of Merchant Growth & Retention

Head of Merchant Growth & Retention

Bask Health · United States (Remote) · Full-time · Posted 2026-11-13

Workplace: remote

Department: Customer Success

Description

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, merchant growth and retention start with understanding the businesses behind our customer accounts. We value people who know how online merchants operate, recognize what drives long-term customer relationships, and build teams that help entrepreneurs succeed while supporting sustainable business growth.

About the Role

We're looking for a Head of Merchant Growth & Retention to lead Bask Health's merchant retention strategy, develop opportunities for existing account growth, and build a customer success organization that supports long-term merchant relationships.

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

You'll be responsible for helping merchants achieve value from Bask Health while improving customer retention and identifying appropriate opportunities to expand existing relationships.

Our merchants 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 operations, online storefronts, merchant economics, and the challenges entrepreneurs face when building and scaling businesses.

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

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

You'll establish processes for understanding each merchant's business goals, platform usage, operational challenges, and potential growth opportunities.

You'll help the team recognize when merchants are successfully adopting the platform and when they may need additional support.

You'll develop proactive strategies for identifying merchants at risk of leaving or reducing their engagement.

You'll establish customer health monitoring practices that provide visibility into merchant retention risks.

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

You'll establish expectations for proactive merchant communication, account planning, and follow-through.

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

You'll help team members strengthen their commercial judgment, merchant relationship management, renewal preparation, and account growth skills.

You'll build a team culture that values initiative, accountability, and a practical understanding of merchant businesses.

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

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

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

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

You'll establish processes for understanding why merchants leave and identifying recurring causes of churn.

You'll analyze merchant feedback, account engagement, and operational patterns to recommend improvements.

You'll create proactive retention strategies for merchants experiencing dissatisfaction, technical problems, or declining engagement.

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

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

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

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

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

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

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

You'll identify opportunities for merchants 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 merchant satisfaction, adoption, and retention.

You'll communicate merchant feedback, product limitations, and e-commerce-related workflow 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 merchants from successfully launching or operating their businesses.

You'll support improvements to merchant onboarding, platform 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 merchant needs without promising unsupported functionality.

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

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

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

You'll develop scalable merchant 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 merchant 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 merchant 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 merchant growth performance, retention trends, and emerging risks.

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

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

You'll develop strategies that strengthen long-term merchant 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 recent e-commerce experience.

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

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

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

What You'll Do

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

Benefits

• 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 merchant retention and account growth strategies.
• Proven ability to lead merchant 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 merchant 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 merchant stakeholders.
• Ability to lead strategic merchant 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 merchant feedback into operational and product recommendations.
• Experience building merchant 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 merchant 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 merchant accounts.
• Experience managing enterprise merchant 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 merchant segmentation and account assignment models.
• Experience building customer success teams during periods of growth.
• Experience leading cross-functional merchant retention initiatives.
• Experience developing merchant 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.

Apply

Apply at Bask Health

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