[Hiring] Head of Merchant Success @Bask Health

Role Description

We're looking for a Head of Merchant Success to lead our merchant-facing customer success strategy and help businesses using Bask Health achieve long-term success. This role is responsible for leading customer success operations, developing a high-performing team, improving merchant retention, and creating opportunities for sustainable account growth.

• Oversee how Bask Health supports merchants throughout the post-sale customer lifecycle, from onboarding and activation through adoption, renewals, retention, and expansion.
• Establish a merchant success strategy that aligns customer outcomes with Bask Health's broader business priorities.
• Define how the team engages merchants at different stages of their relationship with the platform.
• Build clear expectations for onboarding, account ownership, customer communication, escalation management, and renewal preparation.
• Lead, coach, and develop customer success managers and other merchant-facing team members.
• Establish performance standards and help team members develop stronger account management, commercial judgment, and problem-solving skills.
• Create an environment where team members take initiative, follow through on commitments, and understand the businesses they support.
• Work with leadership to define the appropriate customer segmentation model and determine resource allocation across merchant accounts.
• Develop account coverage strategies for strategic customers, growing merchants, and smaller businesses.
• Establish processes for monitoring merchant engagement, platform adoption, account health, and retention risk.
• Develop reporting that helps leadership understand the performance of the merchant success function.
• Track relevant indicators such as customer retention, churn, renewals, expansion, onboarding progress, and account engagement.
• Identify patterns in merchant behavior that indicate opportunities for improvement or potential account risk.
• Create proactive strategies to address customer dissatisfaction, operational friction, and declining engagement.
• Oversee important merchant escalations and ensure the appropriate teams are involved in resolving them.
• Build relationships with key merchant stakeholders, including founders, executives, and business owners.
• Participate in strategic account conversations when leadership involvement can help strengthen relationships or resolve difficult issues.
• Help the team conduct effective business reviews and maintain meaningful conversations about merchant goals and performance.
• Work closely with sales leadership to coordinate customer transitions, renewal preparation, and appropriate expansion opportunities.
• Establish clear boundaries and handoffs between customer success, sales, technical support, and implementation teams.
• Ensure merchants receive consistent information and understand which team is responsible for their requests.
• Collaborate with product and engineering teams to communicate recurring merchant challenges, product feedback, and operational needs.
• Use customer insights to help inform product priorities and improve the merchant experience.
• Work with technical support and customer success engineering teams to address platform issues that affect adoption or retention.
• Identify recurring technical problems that create unnecessary friction for merchants.
• Support improvements to merchant onboarding, product education, and customer-facing resources.
• Develop scalable processes that allow the team to support a growing merchant base without sacrificing service quality.
• Evaluate existing customer success tools, workflows, and documentation to identify opportunities for improvement.
• Establish clear procedures for managing customer escalations, tracking commitments, and communicating across teams.
• Help develop playbooks for merchant onboarding, adoption, renewals, retention, and expansion.
• Collaborate with leadership on organizational planning, staffing needs, and team development.
• Participate in hiring and evaluating customer success talent as needed.
• Create a consistent approach to performance coaching, feedback, and professional development.
• Ensure the team understands how to communicate effectively with entrepreneurs and business owners who expect practical solutions.
• Help merchants understand how Bask Health's capabilities can support their business operations.
• Ensure the team develops enough product knowledge to guide merchants appropriately and recognize when specialist assistance is needed.
• Establish clear boundaries between merchant success responsibilities and clinical, pharmacy, or compliance decisions.
• Coordinate with authorized teams when merchant issues involve regulated healthcare activities.
• Ensure the team follows appropriate security, privacy, and customer information-handling procedures.
• Work directly with company leadership to communicate merchant success performance, emerging risks, and opportunities for improvement.
• Balance customer advocacy with commercial priorities and operational realities.
• Develop strategies that strengthen long-term customer 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 leading customer onboarding, adoption, retention, renewal, and expansion initiatives.
• Proven ability to build and improve customer success processes.
• Experience managing customer success teams responsible for significant customer portfolios.
• Demonstrated ability to coach, develop, and evaluate customer-facing employees.
• Experience creating customer segmentation and account coverage strategies.
• Strong understanding of customer retention, churn, account health, and renewal performance.
• Experience using customer success metrics to evaluate team effectiveness.
• Ability to develop and execute strategies for improving customer retention.
• 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 handle complex customer escalations and sensitive commercial conversations.
• Experience collaborating with sales, product, engineering, and company leadership.
• Ability to translate customer feedback into operational and product recommendations.
• Experience building onboarding, account management, and retention playbooks.
• Strong written and verbal communication skills.
• Ability to present customer success performance and recommendations 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 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.
• Familiarity with subscription commerce and recurring-revenue business models.
• Experience improving gross revenue retention and net revenue retention.
• Experience developing customer health scoring and churn prediction processes.
• Experience establishing customer success performance dashboards.
• 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 customer retention initiatives.
• Experience developing commercial expansion processes with sales teams.
• Experience improving technical onboarding and customer 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.