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. 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 developing customer success strategies that support retention and account expansion. - Proven ability to lead customer 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 customer engagement. - Demonstrated experience identifying and 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 lead strategic account reviews, renewal discussions, and expansion conversations. - Experience handling complex customer escalations and retention risks. - Experience collaborating with sales, product, engineering, and company leadership. - Ability to translate customer feedback into operational and product recommendations. - Experience building customer success and account expansion playbooks. - Strong written and verbal communication skills. - Ability to present customer success 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 customer and team outcomes. Nice to Have - Experience leading customer success or account expansion 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. - Experience improving gross revenue retention and net revenue retention. - Experience developing churn prediction and customer health scoring processes. - Experience creating renewal forecasting and account expansion reporting. - Experience designing upsell, cross-sell, and account growth processes. - Experience collaborating with sales on expansion opportunities. - 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 customer lifecycle and expansion 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.