Head of Customer Education
Location: Remote (U.S.-based), East Coast hours; up to 20% travel across the U.S.
Employment Type: Full-Time (W2)
Industry: Health Technology / SaaS
Reports To: Chief Customer Officer
Direct Reports: None at the start; a small team to be built as the function grows
Travel: 20% all over the US. CSMs will also travel but you may need to jump in.
About This Opportunity
Purple Squirrel Enterprises has been supporting startups and global firms through growth, change, and expansion for 19+ years. We provide flexible HR and recruiting solutions that allow leaders to focus on strategy while we handle people operations — and this search is no exception.
We are exclusively engaged by a high-growth health technology company to help them identify and hire exceptional talent for this role. We are embedded directly with their leadership team, have deep knowledge of the company, the culture, and what it takes to succeed here — and we will be your dedicated recruiting partner from first conversation through offer.
This is not a blind submission. When you apply, you are working with a team that knows this opportunity inside and out and will advocate for you every step of the way.
💜 If this opportunity resonates with you, we encourage you to apply. We will be in touch promptly.
Applications submitted directly to our client will be redirected back to Purple Squirrel Enterprises. To be considered for this role, all candidates must apply through this posting.
About Our Client
Our client was founded on a mission to transform medication management for vulnerable populations through innovation, accountability, and compassion. Their platform empowers care teams by simplifying complex workflows, preventing medication errors, and ensuring compliance — ultimately improving safety, outcomes, and independence for individuals in long-term care and other specialized care settings.
They operate like a family: supporting one another both professionally and personally, listening first, building with empathy, and remaining committed to solving problems that have a meaningful, real-world impact on people's lives.
💜 This company was built around a cause that is both personal and urgent. That authenticity shows in how they operate, who they hire, and what they build. If you are looking for work that matters — this is it.
A Note on Title & Scope
Our client is posting this role as Head of Customer Education. The final title (for example, Director) and compensation will reflect the experience and level of the person they hire, and will be part of our conversation as we get to know your background.
About the Role
As part of the Customer Experience team, the Head of Customer Education will own training and certification across the company’s customer base, ensuring customers’ teams are fully trained, operationally prepared, and equipped to get lasting value from the platform. This is a foundational, hands-on build role.
Today, training is delivered largely by people, which creates a great experience but does not scale. In 2027, the company is moving to a self-service-first model: end users complete a structured onboarding path, practice in a safe training environment, and earn certification through role-based assessments. Certification here means verified competency on the platform, not restriction, and the goal is to certify as many people as possible. You will own that transition, including bringing in a new learning management system (LMS), adding short-form microlearning (brief videos and assessments) so people can learn the way that works for them, and partnering with Product and Engineering on the in-platform learning experience.
You will work across state program partners, enterprise accounts, and commercial customers, training end users who are often not tech savvy and who work in high-turnover, regulated care settings. The role begins with no direct reports, and you will be a player/coach who stays hands-on while building a small…