Head of Customer Success

Location: Remote: Exceptional remote candidates may be considered with frequent travel to client sites. Candidates located in New Jersey, Pennsylvania, or the Greater New York City area are strongly preferred

Experience: 7+ years of relevant experience
Travel: Regular travel across Illinois for district meetings, conferences, and relationship development

About InSite Health

InSite Health is building the operating system for school and community wellness. We partner with school districts, government entities, and healthcare organizations to deliver software-enabled solutions that improve access, coordination, and outcomes across behavioral health and student wellness.

We are growing rapidly across multiple states and are looking for a senior customer success leader who can build the infrastructure, team, and operating discipline required to support that growth.

The Role

We are seeking a Head of Customer Success to build and lead the Customer Success function at InSite Health.

This is not a role for someone who wants to inherit a mature customer success organization and simply manage it. We are looking for a zero-to-one builder who has previously designed and scaled customer success infrastructure inside a rapidly growing company.

You will be responsible for creating the systems, processes, team structure, operating cadence, and customer experience required to successfully support a growing portfolio of school districts, government agencies, and other institutional customers.

At the same time, this is an extremely hands-on role. You will personally work with customers, participate in implementations and launches, visit client sites, troubleshoot problems, lead executive relationships, and step directly into the work whenever necessary.

The right candidate has built before, led before, and is still excited to roll up their sleeves and execute.

What You’ll Own

Build the Customer Success Function

• Design and build InSite Health’s Customer Success organization from the ground up as the company rapidly scales.

• Establish the processes, playbooks, systems, KPIs, and operating rhythms required to manage customers consistently and effectively.

• Define customer segmentation, account ownership, engagement models, escalation processes, and service standards.

• Build scalable processes for onboarding, implementation coordination, adoption, ongoing account management, renewals, and expansion.

• Develop the organizational structure and hiring roadmap for the Customer Success team.

• Recruit, develop, and lead a high-performing team of Customer Success and Account Management professionals.

• Determine what should be standardized, automated, or technology-enabled while maintaining a highly responsive customer experience.

Own the Customer Experience

• Take executive ownership of the customer relationship from contract signature through launch, adoption, renewal, and expansion.

• Develop deep relationships with superintendents, district administrators, government officials, clinical leaders, and other senior stakeholders.

• Ensure customers experience a high-touch, responsive, and exceptionally organized partnership with InSite.

• Regularly travel to school districts and government client sites for launches, trainings, executive meetings, business reviews, and relationship management.

• Personally step into high-priority accounts or challenging situations when necessary.

• Establish executive business review processes and ensure customers clearly understand utilization, outcomes, progress, and opportunities for additional value.

Drive Successful Implementations and Adoption

• Work cross-functionally with Sales, Product, Operations, Clinical, and Technology teams to ensure smooth transitions from signed contract to successful customer launch.

• Create repeatable implementation and onboarding processes for customers that may include multiple products, services, departments, and stakeholder groups.

• Identify risks early and ensure issues are resolved quickly.

• Develop adoption strategies that ensure customers actively utilize the products and services they purchase.

• Build processes for customer education, training, change management, and ongoing engagement.

• Translate customer feedback into actionable insights for Product and company leadership.

Retention, Expansion & Customer Health

• Establish customer health scoring and early-warning systems for accounts at risk.

• Own retention and renewal performance across the customer base.

• Identify expansion opportunities within existing customers and work collaboratively with Sales to grow relationships.

• Develop clear forecasting around renewals, expansions, implementation progress, customer satisfaction, and account risk.

• Build dashboards and reporting that give leadership real-time visibility into the health of the customer base.

• Help create a culture where retention and customer outcomes are company-wide responsibilities.

Build for Scale

• Implement and optimize Customer Success technology, CRM workflows, automation, dashboards, and reporting.

• Leverage technology and AI wherever appropriate to improve efficiency and customer responsiveness.

• Create processes capable of supporting significant growth without sacrificing quality.

• Establish clear ownership and accountability across Customer Success, Sales, Operations, Product, and other functions.

• Develop the infrastructure needed to support customers across multiple states, regulatory environments, and product offerings.

What We’re Looking For

• 7+ years of experience across Customer Success, Account Management, Implementation, or related customer-facing leadership roles.

• Significant experience leading Customer Success within a rapidly growing company.

• Demonstrated experience building or materially scaling a Customer Success organization from an early stage.

• Proven experience designing processes, infrastructure, playbooks, KPIs, and team structures—not simply operating within systems someone else created.

• Experience hiring, developing, and managing high-performing teams.

• Strong executive presence and comfort managing relationships with senior customer stakeholders.

• Experience working with complex institutional or enterprise customers.

• Ideally, experience within K-12 education, education technology, government technology, public-sector software, healthcare technology, or another regulated industry.

• Strong preference for candidates who have worked with a software or technology-enabled product.

• Experience managing complex implementations involving multiple stakeholder groups.

• Strong operational and analytical orientation with the ability to create structure in a fast-moving environment.

• Comfort working with CRM, Customer Success platforms, data, reporting, and workflow automation.

• Excellent written and verbal communication skills.

• Ability and willingness to travel frequently to customer sites.

The Profile That Will Thrive Here

You are likely someone who has joined a company before the Customer Success organization was fully built and helped create what came next.

You enjoy taking something that is working informally and turning it into a repeatable, measurable operating system.

You can spend the morning designing a customer health framework, the afternoon meeting with a superintendent or government executive, and the evening helping your team solve an urgent implementation issue.

You are equally comfortable setting strategy and doing the work yourself.

You move quickly, communicate clearly, hold yourself and others accountable, and are energized—not intimidated—by rapid growth and changing priorities.

Most importantly, you care deeply about customers and take personal ownership of making sure they are successful.

Location & Travel

Candidates located in New Jersey, Pennsylvania, or the Greater New York City area are strongly preferred. The role will operate in a hybrid environment with regular in-person collaboration.

Exceptional remote candidates may also be considered, provided they are comfortable with frequent travel to customer sites and company meetings. Travel is an important component of this position and will vary based on customer launches and business needs.