Head of Customer Education
- Compensation
- Not disclosed
- Location
- Baltimore, MD
- Work setup
- Remote
- Seniority
- C level
- Employment
- Full time
- Experience
- 5+ years
- Category
- Not specified
- Posted
Skills
Must have
- 5+ years of experience in customer education, training, enablement, or L&D, including designing and delivering training curricula for end users of a healthcare SaaS platform
- Hands-on experience building training materials, including presentations, job aids, help documentation, video walkthroughs, and self-serve learning resources
- Experience conducting structured training sessions both in person and virtually
- Familiarity with adult learning principles and instructional design methodologies (ADDIE, Kirkpatrick, etc.)
- Experience selecting and implementing an LMS or comparable learning platform, including integrations and rollout
- Experience designing certification and assessment programs, including pass standards and recertification models
- Demonstrated ability to design and run a train-the-trainer program
- Experience leading, hiring, onboarding, and developing team members; about a year of people leadership with a clear aptitude to lead will be considered
- Experience in a highly regulated environment, with a strong understanding of healthcare documentation standards and compliance-driven workflows, including HIPAA-aware handling of training data
- Strong data orientation, with experience tying learning outcomes to retention, satisfaction, or health score measures
- Excellent written and verbal communication, with the ability to translate complex workflows into clear guidance for users across a wide range of technical comfort
- Ability to manage multiple concurrent projects and priorities in a fast-moving startup environment
- Ability to travel up to 20% across the U.S. to support on-site customer training and onboarding
- Fully remote and U.S.-based, working East Coast hours (West Coast candidates should expect some early mornings and early meetings)
Nice to have
- Experience working with IDD, behavioral health, or long-term care provider organizations
- Familiarity with state-regulated medication administration programs
- Experience partnering with Product and Engineering to shape in-product learning experiences
- Experience training users on hardware or connected devices alongside software
- Background in healthcare operations, compliance, quality management, or healthcare IT
- Familiarity with SCORM/xAPI content standards, digital badging or credentialing platforms, and learning record stores
- Experience with accessible, mobile-first, low-bandwidth, and multilingual learning design
Full description
Head of Customer EducationLocation: 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.