[Hiring] Head of Merchant Growth & Retention @Bask Health

Role Description

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.

• Responsible for helping merchants achieve value from Bask Health while improving customer retention and identifying appropriate opportunities to expand existing relationships.
• Develop a merchant growth and retention strategy that aligns customer needs with Bask Health's broader business objectives.
• Define how the team approaches merchant onboarding, adoption, engagement, renewals, retention, and account expansion.
• Establish processes for understanding each merchant's business goals, platform usage, operational challenges, and potential growth opportunities.
• Help the team recognize when merchants are successfully adopting the platform and when they may need additional support.
• Develop proactive strategies for identifying merchants at risk of leaving or reducing their engagement.
• Establish customer health monitoring practices that provide visibility into merchant retention risks.
• Work with customer success managers to ensure merchant goals, account priorities, and growth opportunities are clearly documented.
• Establish expectations for proactive merchant communication, account planning, and follow-through.
• Lead, coach, and develop customer success team members within the approved organizational structure.
• Help team members strengthen their commercial judgment, merchant relationship management, renewal preparation, and account growth skills.
• Build a team culture that values initiative, accountability, and a practical understanding of merchant businesses.
• Work with leadership to establish merchant segmentation and account coverage strategies.
• Help determine how resources should be allocated across strategic merchants, growing businesses, and smaller accounts.
• Develop performance metrics and reporting practices for merchant growth and retention.
• Monitor relevant indicators such as merchant churn, gross revenue retention, net revenue retention, renewals, expansion, and product adoption.
• Establish processes for understanding why merchants leave and identifying recurring causes of churn.
• Analyze merchant feedback, account engagement, and operational patterns to recommend improvements.
• Create proactive retention strategies for merchants experiencing dissatisfaction, technical problems, or declining engagement.
• Oversee important merchant escalations that may affect retention or long-term account value.
• Build relationships with strategic merchant stakeholders, including founders, executives, and business owners.
• Participate in high-priority merchant conversations when leadership involvement can help strengthen relationships or address concerns.
• Guide the team in conducting business reviews focused on merchant goals, platform adoption, business progress, and opportunities for growth.
• Work closely with sales leadership to coordinate renewal preparation and account expansion opportunities.
• Establish clear responsibilities between merchant success and sales for identifying, qualifying, and pursuing expansion opportunities.
• Help ensure commercial conversations are grounded in merchant needs and supported platform capabilities.
• Identify opportunities for merchants to adopt additional features or expand their use of Bask Health when those capabilities support their business goals.
• Collaborate with product and engineering teams to address recurring issues that affect merchant satisfaction, adoption, and retention.
• Communicate merchant feedback, product limitations, and e-commerce-related workflow challenges to the appropriate internal teams.
• Work with technical support and customer success engineering teams to address technical problems that create churn risk.
• Help identify recurring implementation challenges that prevent merchants from successfully launching or operating their businesses.
• Support improvements to merchant onboarding, platform education, and implementation handoffs.
• Ensure the customer success team understands how Bask Health's capabilities support different merchant business models.
• Help the team connect these capabilities to practical merchant needs without promising unsupported functionality.
• Establish clear processes for recognizing when merchant requests require technical, clinical, pharmacy, or compliance expertise.
• Coordinate with authorized teams when issues involve regulated healthcare activities.
• Ensure merchant-facing processes follow appropriate privacy, security, and information-handling requirements.
• Develop scalable merchant retention and expansion playbooks.
• Evaluate customer success tools, workflows, and reporting systems to identify opportunities for improvement.
• Create consistent processes for tracking merchant renewals, retention risks, expansion opportunities, and customer commitments.
• Collaborate with leadership on organizational planning, staffing needs, and team development.
• Participate in hiring and evaluating customer success talent as needed.
• Establish performance coaching and professional development practices that reinforce strong merchant account management and commercial execution.
• Help create effective collaboration between customer success, sales, product, engineering, and technical support teams.
• Work directly with company leadership to communicate merchant growth performance, retention trends, and emerging risks.
• Provide recommendations for improving recurring-revenue performance through stronger post-sale merchant engagement.
• Balance merchant advocacy with commercial priorities and operational realities.
• Develop strategies that strengthen long-term merchant relationships while supporting responsible revenue growth.

Qualifications

• 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.