Head of Customer Success & Expansion

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 success and expansion go hand in hand. We believe the strongest customer relationships are built by helping businesses achieve real results, understanding how their needs evolve, and identifying opportunities to help them get more value from the platform as they grow.

About the Role

We're looking for a Head of Customer Success & Expansion to lead Bask Health's post-sale customer success organization, strengthen customer relationships, improve retention, and develop opportunities for growth within our existing customer base.

This role combines customer success leadership, strategic account management, commercial strategy, and cross-functional execution.

You'll be responsible for building a customer success function that helps customers achieve their business goals while supporting long-term retention and appropriate account expansion.

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 operations, merchant-facing software, and the challenges businesses face when launching and scaling online.

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

You'll oversee the post-sale customer lifecycle, including onboarding, activation, adoption, account management, renewals, retention, and expansion.

You'll establish clear processes for understanding customer goals and identifying opportunities to help them get more value from the platform.

You'll help the team recognize when customers are ready to adopt additional supported capabilities or expand their relationship with Bask Health.

You'll develop a consistent approach to strategic account planning and customer success management.

You'll establish expectations for proactive customer communication, account ownership, 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 account management skills, commercial judgment, customer communication, and ability to identify appropriate expansion opportunities.

You'll create a team culture that values initiative, accountability, customer outcomes, and responsible commercial growth.

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 success, retention, and expansion.

You'll monitor customer retention, churn, renewals, product adoption, account engagement, and expansion performance.

You'll track relevant recurring-revenue indicators, including gross revenue retention and net revenue retention where applicable.

You'll establish processes for identifying customers who may be at risk of leaving or reducing their engagement.

You'll develop proactive strategies for addressing customer dissatisfaction and strengthening long-term relationships.

You'll work with customer success managers to ensure account goals, risks, opportunities, and next steps are clearly documented.

You'll oversee important customer escalations that may affect retention or account growth.

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

You'll participate in executive-level customer conversations when leadership involvement can help strengthen relationships or support complex account discussions.

You'll guide the team in conducting business reviews focused on customer goals, platform adoption, business progress, and future needs.

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

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

You'll ensure commercial conversations are based on customer needs and supported platform capabilities.

You'll help the team identify customers who may benefit from additional platform features, increased usage, or other approved expansion opportunities.

You'll develop processes for documenting and tracking expansion opportunities within existing accounts.

You'll collaborate with product and engineering teams to address recurring issues that affect customer adoption, satisfaction, and long-term account value.

You'll communicate customer feedback, product limitations, and emerging business needs to the appropriate internal teams.

You'll work with technical support and customer success engineering teams to resolve technical challenges that create retention risk or prevent customers from expanding their use of the platform.

You'll help identify recurring onboarding and implementation challenges that delay customer success.

You'll support improvements to customer onboarding, product 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 or unapproved product changes.

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 success, retention, and expansion playbooks.

You'll evaluate existing 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 success performance, retention trends, expansion opportunities, 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 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 recent 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 building processes, coaching teams, managing strategic accounts, and making data-informed commercial decisions.

Success in this role means building a high-performing customer success organization that improves customer retention, strengthens strategic relationships, increases appropriate account expansion, and contributes directly to Bask Health's long-term growth.

What You'll Do

• Lead Bask Health's customer success and expansion strategy.
• Oversee post-sale customer success operations and account management.
• Develop scalable processes for customer onboarding, adoption, renewals, retention, and expansion.
• Establish customer health monitoring and retention-risk identification practices.
• Build proactive strategies to improve retention and reduce preventable 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 strategic account coverage strategies.
• Monitor customer retention, churn, renewals, and expansion performance.
• Track gross revenue retention and net revenue retention where applicable.
• Establish customer success and expansion reporting practices.
• Identify opportunities for existing customers to adopt additional supported platform capabilities.
• Develop processes for tracking and managing account expansion opportunities.
• Oversee strategic customer relationships and executive-level engagements.
• Guide customer success managers in conducting business reviews and renewal discussions.
• Support appropriate upsell and 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 adoption and retention.
• Coordinate with technical support and customer success engineering teams.
• Improve onboarding and implementation handoffs that affect long-term customer success.
• Develop customer success, retention, and expansion playbooks.
• Establish consistent processes for documenting account risks and growth 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 effective collaboration between customer success and other departments.
• Promote accountability for customer retention and account expansion 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 success, retention, expansion, and risks.
• Take ownership of the customer success function's overall effectiveness and commercial contribution.