Head of Customer Outcomes

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 outcomes are about helping entrepreneurs and businesses turn our software into meaningful results. We value people who understand customer goals, take responsibility for delivering value, and build lasting relationships through strong execution, practical problem-solving, and measurable progress.

About the Role

We're looking for a Head of Customer Outcomes to lead Bask Health's customer success strategy with a strong focus on measurable customer value, platform adoption, retention, and long-term account growth.

This role is responsible for building a customer success function that understands what customers are trying to accomplish and helps them achieve those goals.

You'll lead customer success operations, develop a high-performing team, and establish processes that connect customer engagement to meaningful business outcomes.

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 operations, and the challenges entrepreneurs face when building and scaling online businesses.

You'll develop a customer outcomes strategy that aligns customer goals with Bask Health's capabilities and business priorities.

You'll define how the team identifies customer objectives during onboarding and tracks progress throughout the customer lifecycle.

You'll establish a consistent approach to customer success planning, account reviews, adoption strategies, and outcome measurement.

You'll help the team understand the difference between customers simply using the platform and customers achieving meaningful value from it.

You'll develop frameworks for evaluating customer adoption, business engagement, account health, and retention risk.

You'll work with customer success managers to ensure customer goals are documented, understood, and revisited over time.

You'll establish clear expectations for account ownership, customer communication, and proactive engagement.

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

You'll help team members strengthen their strategic account management, commercial judgment, and problem-solving skills.

You'll create an environment where team members take ownership of customer outcomes rather than focusing only on completing tasks or responding to requests.

You'll work with leadership to develop appropriate customer segmentation and account coverage strategies.

You'll help determine how the team should support strategic accounts, growing merchants, and smaller businesses.

You'll establish meaningful performance metrics for customer success and customer outcomes.

You'll monitor customer retention, churn, renewals, expansion, product adoption, and other relevant indicators of customer health.

You'll develop reporting that helps leadership understand how customer success activities contribute to business performance.

You'll identify patterns in customer behavior that indicate successful adoption, declining engagement, or potential account risk.

You'll create proactive strategies to address customers who are struggling to achieve their goals.

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

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 address challenges.

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

You'll collaborate with sales leadership to support renewal preparation and identify appropriate account expansion opportunities.

You'll help establish processes for identifying customers who may benefit from additional supported platform capabilities.

You'll ensure expansion conversations are grounded in customer needs and demonstrated value.

You'll work closely with product and engineering teams to communicate customer feedback, adoption challenges, and recurring product limitations.

You'll use customer insights to help inform product improvements that strengthen customer outcomes.

You'll collaborate with technical support and customer success engineering teams to address implementation or technical obstacles affecting adoption.

You'll help identify recurring technical problems that prevent customers from achieving important business goals.

You'll support improvements to customer onboarding, product education, and implementation handoffs.

You'll help ensure customers understand how to use Bask Health's capabilities effectively.

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

You'll ensure the customer success team understands the platform well enough to connect its capabilities to customer business needs.

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 the team follows appropriate security, privacy, and customer information-handling procedures.

You'll develop scalable customer success playbooks and operational processes.

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

You'll create a consistent approach to documenting customer goals, success plans, risks, and follow-up 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 accountability for customer results.

You'll help create clear collaboration between customer success, sales, product, engineering, and technical support teams.

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

You'll help leadership understand how customer value realization affects retention, expansion, and long-term account relationships.

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

You'll develop strategies that strengthen customer relationships while supporting responsible recurring-revenue growth.

We're looking for a leader with substantial post-sale customer success experience, proven team management ability, and meaningful e-commerce experience.

You should understand how merchant-facing SaaS businesses operate and how customer outcomes influence retention and long-term account value.

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

Success in this role means creating a customer success function that consistently helps customers achieve meaningful results, improves retention, supports account growth, and demonstrates the value of Bask Health's platform.

What You'll Do

• Lead Bask Health's customer outcomes strategy and customer success operations.
• Establish processes for identifying and documenting customer business goals.
• Develop customer success plans focused on measurable results.
• Build frameworks for tracking customer adoption and value realization.
• Lead and coach customer success team members within the approved organization.
• Establish clear expectations for account ownership and proactive customer engagement.
• Develop customer segmentation and account coverage strategies.
• Monitor customer retention, churn, renewals, and expansion performance.
• Establish customer outcomes metrics and reporting practices.
• Identify customers who are struggling to achieve expected results.
• Develop proactive strategies to improve adoption and reduce retention risk.
• Oversee strategic customer relationships and executive-level engagements.
• Guide customer success managers in conducting outcome-focused business reviews.
• Support renewal preparation and appropriate account expansion opportunities.
• Collaborate with sales on account growth strategies.
• Work with product and engineering on customer adoption challenges.
• Coordinate with technical support and customer success engineering teams.
• Improve onboarding and implementation handoffs.
• Develop customer success playbooks and internal training resources.
• Establish consistent processes for documenting customer goals and account risks.
• Build reporting that connects customer success activities to business performance.
• Identify recurring customer obstacles and recommend improvements.
• Oversee important customer escalations affecting account health.
• Coach team members on strategic account management and commercial judgment.
• Support organizational planning and customer success hiring.
• Improve customer success tools, workflows, and documentation.
• Establish clear collaboration between customer success and other departments.
• Promote accountability for measurable customer 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 outcomes, retention, and risks.
• Take ownership of the customer success function's effectiveness and long-term 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 developing customer success strategies focused on measurable customer outcomes.
• Proven ability to lead customer onboarding, adoption, retention, renewal, and expansion initiatives.
• Experience creating and managing customer success plans.
• 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 measuring customer adoption and value realization.
• Ability to develop strategies for improving customer retention and long-term engagement.
• 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 lead strategic account reviews and customer outcome discussions.
• Experience handling complex customer escalations.
• Experience collaborating with sales, product, engineering, and company leadership.
• Ability to translate customer feedback into operational and product recommendations.
• Experience building customer success playbooks and scalable processes.
• Strong written and verbal communication skills.
• Ability to present customer outcomes and business 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 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 developing customer value realization frameworks.
• Experience creating customer outcome scorecards and success plans.
• Experience improving gross revenue retention and net revenue retention.
• Experience developing customer health scoring and churn prediction processes.
• Experience building customer success dashboards and reporting.
• 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 account 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.