Head of Merchant Success

Head of Merchant Success

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 success is about helping business owners build lasting, successful relationships with our platform. We value people who understand how e-commerce businesses operate, take responsibility for customer outcomes, and know how to build teams and processes that help merchants succeed at scale.

About the Role

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.

You'll oversee how Bask Health supports merchants throughout the post-sale customer lifecycle, from onboarding and activation through adoption, renewals, retention, and expansion.

Our merchants include entrepreneurs, e-commerce operators, online business owners, and healthcare businesses using our platform to launch and manage direct-to-consumer telehealth services.

You'll bring a strong understanding of e-commerce operations and the challenges businesses face when launching and growing online.

You'll establish a merchant success strategy that aligns customer outcomes with Bask Health's broader business priorities.

You'll define how the team engages merchants at different stages of their relationship with the platform.

You'll build clear expectations for onboarding, account ownership, customer communication, escalation management, and renewal preparation.

You'll lead, coach, and develop customer success managers and other merchant-facing team members within the approved organizational structure.

You'll establish performance standards and help team members develop stronger account management, commercial judgment, and problem-solving skills.

You'll help create an environment where team members take initiative, follow through on commitments, and understand the businesses they support.

You'll work with leadership to define the appropriate customer segmentation model and determine how resources should be allocated across merchant accounts.

You'll help develop account coverage strategies for strategic customers, growing merchants, and smaller businesses.

You'll establish processes for monitoring merchant engagement, platform adoption, account health, and retention risk.

You'll develop reporting that helps leadership understand the performance of the merchant success function.

You'll track relevant indicators such as customer retention, churn, renewals, expansion, onboarding progress, and account engagement.

You'll identify patterns in merchant behavior that indicate opportunities for improvement or potential account risk.

You'll create proactive strategies to address customer dissatisfaction, operational friction, and declining engagement.

You'll oversee important merchant escalations and ensure the appropriate teams are involved in resolving them.

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

You'll participate in strategic account conversations when leadership involvement can help strengthen relationships or resolve difficult issues.

You'll help the team conduct effective business reviews and maintain meaningful conversations about merchant goals and performance.

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

You'll establish clear boundaries and handoffs between customer success, sales, technical support, and implementation teams.

You'll help ensure merchants receive consistent information and understand which team is responsible for their requests.

You'll collaborate with product and engineering teams to communicate recurring merchant challenges, product feedback, and operational needs.

You'll use customer insights to help inform product priorities and improve the merchant experience.

You'll work with technical support and customer success engineering teams to address platform issues that affect adoption or retention.

You'll help identify recurring technical problems that create unnecessary friction for merchants.

You'll support improvements to merchant onboarding, product education, and customer-facing resources.

You'll develop scalable processes that allow the team to support a growing merchant base without sacrificing service quality.

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

You'll establish clear procedures for managing customer escalations, tracking commitments, and communicating across teams.

You'll help develop playbooks for merchant onboarding, adoption, renewals, retention, and expansion.

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 create a consistent approach to performance coaching, feedback, and professional development.

You'll ensure the team understands how to communicate effectively with entrepreneurs and business owners who expect practical solutions.

You'll help merchants understand how Bask Health's capabilities can support their business operations.

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

You'll ensure the team develops enough product knowledge to guide merchants appropriately and recognize when specialist assistance is needed.

Because Bask Health supports healthcare-related businesses, you'll establish clear boundaries between merchant success responsibilities and clinical, pharmacy, or compliance decisions.

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

You'll ensure the team follows appropriate security, privacy, and customer information-handling procedures.

You'll work directly with company leadership to communicate merchant success performance, emerging risks, and opportunities for improvement.

You'll be expected to 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 experience in post-sale customer success, proven team management ability, and meaningful e-commerce experience.

You should understand how merchant-facing SaaS businesses operate and how customer success contributes to retention, expansion, and long-term account value.

You'll need to be comfortable making decisions, developing processes, coaching team members, and working across departments.

Success in this role means building a merchant success function that improves customer outcomes, strengthens retention, supports account growth, and scales effectively as Bask Health grows.

What You'll Do

• Lead Bask Health's merchant-facing customer success strategy and operations.
• Develop a scalable approach to merchant onboarding, adoption, retention, and expansion.
• Manage and coach customer success team members within the approved organization.
• Establish clear expectations for account ownership and customer communication.
• Build customer success processes and operating procedures.
• Develop merchant segmentation and account coverage strategies.
• Establish account health monitoring and retention-risk identification practices.
• Create proactive strategies to reduce customer churn.
• Oversee renewal preparation and customer retention initiatives.
• Partner with sales on appropriate account expansion opportunities.
• Define customer success performance metrics and reporting practices.
• Monitor merchant engagement, adoption, retention, and account growth.
• Review customer success performance and identify improvement opportunities.
• Build relationships with strategic merchants and executive stakeholders.
• Participate in high-priority merchant conversations and escalations.
• Guide the team in developing customer success plans and account strategies.
• Improve merchant onboarding and activation processes.
• Develop customer success playbooks and internal training resources.
• Establish consistent escalation and follow-up procedures.
• Coordinate with technical support and customer success engineering teams.
• Collaborate with product and engineering on recurring merchant challenges.
• Share customer feedback and insights with company leadership.
• Help prioritize improvements that strengthen merchant experience and retention.
• Support organizational planning and customer success hiring.
• Coach team members on account management, communication, and commercial judgment.
• Improve customer success tools, workflows, and documentation.
• Establish clear collaboration between sales, customer success, and technical teams.
• Promote strong accountability and follow-through across merchant-facing functions.
• Ensure appropriate privacy, security, and information-handling practices.
• Escalate clinical, pharmacy, and compliance matters to authorized teams.
• Provide leadership with clear updates on merchant success performance and risks.
• Take ownership of the merchant success function's overall effectiveness and results.

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 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.

Apply

Apply at Bask Health

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