Head of Customer Success & Strategy

Head of Customer Success & Strategy

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, customer success is about helping businesses achieve meaningful results while building relationships that last. We value leaders who can think strategically, understand the details of customer operations, develop strong teams, and turn good ideas into processes that make a measurable difference.

About the Role

We're looking for a Head of Customer Success & Strategy to lead Bask Health's customer success organization, develop its long-term strategy, and build scalable processes that improve customer outcomes, retention, and operational performance.

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

You'll be responsible for defining how our customer success function operates, how we support different types of customers, and how we measure the value our team delivers.

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

You'll develop a customer success strategy that aligns customer needs, team capabilities, and Bask Health's broader business objectives.

You'll translate company priorities into clear customer success goals, operating plans, and measurable initiatives.

You'll evaluate our existing customer success processes and identify opportunities to improve consistency, accountability, and efficiency.

You'll help determine how the customer success organization should evolve as the platform and customer base grow.

You'll establish clear responsibilities across customer success, account management, onboarding, and related customer-facing functions.

You'll develop customer segmentation strategies that reflect differences in customer needs, account complexity, and business value.

You'll help determine the appropriate level of support and engagement for strategic accounts, growing merchants, and smaller businesses.

You'll establish processes for customer onboarding, activation, adoption, engagement, renewals, retention, and expansion.

You'll help the team understand how customer success activities contribute to measurable customer outcomes.

You'll establish clear expectations for proactive account management, customer communication, and follow-through.

You'll lead, coach, and develop customer success team members within the approved organizational structure.

You'll help managers and individual contributors strengthen their strategic thinking, account management skills, and ability to solve complex customer problems.

You'll establish performance expectations that emphasize customer outcomes, accountability, and consistent execution.

You'll develop management practices that support coaching, performance reviews, and professional development.

You'll work with leadership to evaluate team capacity, staffing needs, and organizational priorities.

You'll participate in hiring and developing customer success talent as needed.

You'll define meaningful performance metrics and reporting practices for the customer success organization.

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

You'll establish processes for analyzing customer success trends and identifying areas that require attention.

You'll develop customer health frameworks that help the team recognize risks and opportunities early.

You'll create strategies for improving customer engagement and reducing preventable churn.

You'll oversee important customer escalations and ensure issues affecting strategic relationships receive appropriate attention.

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

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

You'll guide the team in conducting meaningful customer business reviews focused on goals, progress, challenges, and opportunities.

You'll work closely with sales leadership to improve customer handoffs, renewal preparation, and appropriate account expansion opportunities.

You'll establish clear collaboration between customer success and sales so account responsibilities are understood.

You'll help ensure commercial conversations are grounded in customer needs and supported platform capabilities.

You'll collaborate with product leadership to communicate recurring customer challenges, adoption barriers, and opportunities for improvement.

You'll use customer feedback and operational data to help inform product priorities.

You'll work with engineering and customer success engineering teams to address technical problems affecting customer adoption and retention.

You'll coordinate with technical support teams to improve escalation processes and issue resolution.

You'll identify recurring onboarding and implementation problems that prevent customers from achieving value.

You'll support improvements to customer education, onboarding resources, 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.

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 playbooks, operating procedures, and internal documentation.

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

You'll establish consistent practices for documenting customer goals, account risks, customer commitments, and next steps.

You'll develop operational planning processes that help the team prioritize work effectively.

You'll establish a regular cadence for reviewing customer success performance, strategic initiatives, and operational challenges.

You'll work with leadership to set realistic priorities and allocate resources to the most important customer success initiatives.

You'll identify opportunities to reduce unnecessary manual work and improve team efficiency.

You'll evaluate how customer success processes should change as the customer base becomes larger or more complex.

You'll develop strategies that support consistency without making customer relationships overly rigid or impersonal.

You'll work directly with company leadership to communicate customer success performance, strategic priorities, and emerging risks.

You'll provide recommendations on team structure, customer coverage, retention initiatives, and long-term customer success investments.

You'll help leadership understand how customer success performance affects customer satisfaction, retention, and recurring revenue.

You'll balance customer advocacy with commercial priorities and operational realities.

You'll take responsibility for turning customer success strategy into practical improvements that the team can execute.

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 organizations contribute to customer outcomes and company growth.

You'll need to be comfortable developing strategies, building processes, coaching teams, managing strategic accounts, and making data-informed decisions.

Success in this role means building a customer success organization with a clear strategy, strong leadership, consistent processes, measurable performance, and the ability to support Bask Health's long-term growth.

What You'll Do

• Lead Bask Health's customer success strategy and organizational direction.
• Translate company objectives into customer success goals and operating plans.
• Oversee post-sale customer success operations and account management.
• Develop scalable processes for onboarding, adoption, retention, renewals, and expansion.
• Establish clear customer success team responsibilities and operating standards.
• Lead and coach customer success team members within the approved organization.
• Develop organizational planning and customer success staffing recommendations.
• Establish customer segmentation and account coverage strategies.
• Define customer success performance metrics and reporting practices.
• Monitor retention, churn, renewals, adoption, and account health.
• Develop customer health monitoring and risk identification frameworks.
• Identify opportunities to improve customer outcomes and reduce preventable churn.
• Establish a consistent cadence for customer success performance reviews.
• Oversee strategic customer relationships and executive-level engagements.
• Guide customer success managers in conducting customer business reviews.
• Collaborate with sales on renewals and appropriate account expansion opportunities.
• Establish clear collaboration and handoffs between customer success and sales.
• Work with product leadership on customer feedback and adoption challenges.
• Coordinate with engineering and technical support on customer-impacting issues.
• Improve onboarding and implementation processes that affect customer success.
• Develop customer success playbooks, training resources, and operating procedures.
• Establish consistent documentation practices for account goals, risks, and commitments.
• Evaluate customer success tools, workflows, and reporting systems.
• Identify opportunities to improve operational efficiency and reduce manual work.
• Oversee important customer escalations affecting strategic accounts.
• Coach team members on account management, strategic thinking, and customer communication.
• Support organizational planning, hiring, and professional development.
• Establish effective collaboration between customer success and other departments.
• Promote accountability for customer outcomes and operational execution.
• 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 strategy, performance, and risks.
• Recommend long-term improvements to the customer success organization.
• Take ownership of the customer success function's strategy, effectiveness, and execution.

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 customer success strategy, operations, and team performance.
• 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 and executing customer success strategies.
• Proven ability to lead customer onboarding, adoption, renewal, retention, and expansion initiatives.
• Experience building scalable customer success processes and operating models.
• 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.
• Experience developing customer segmentation and account coverage strategies.
• Ability to translate business objectives into practical customer success initiatives.
• Experience improving customer success team structure, workflows, or operational efficiency.
• 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 and executive-level customer discussions.
• 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 playbooks, training programs, and internal procedures.
• Strong written and verbal communication skills.
• Ability to present customer success strategy and operational 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 strategy 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 designing customer success organizational structures and operating models.
• Experience developing customer success annual or quarterly planning processes.
• Experience creating customer success dashboards and executive reporting.
• Experience developing customer health scoring and churn prediction processes.
• Experience improving gross revenue retention and net revenue retention.
• Experience collaborating with sales on customer expansion strategies.
• 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 success initiatives.
• Experience developing customer 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.

Apply

Apply at Bask Health

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