[Hiring] Head of Customer Education @Purple Squirrel Enterprises

Role Description

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.
• Earn certification through role-based assessments.

You will own that transition, including:

• Bringing in a new learning management system (LMS).
• Adding short-form microlearning (brief videos and assessments).
• 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.

Qualifications

• 5+ years of experience in customer education, training, enablement, or L&D.
• Hands-on experience building training materials.
• Experience conducting structured training sessions both in person and virtually.
• Familiarity with adult learning principles and instructional design methodologies.
• Experience selecting and implementing an LMS or comparable learning platform.
• Experience designing certification and assessment programs.
• Demonstrated ability to design and run a train-the-trainer program.
• Experience leading, hiring, onboarding, and developing team members.
• Experience in a highly regulated environment.
• Strong data orientation.
• Excellent written and verbal communication skills.
• Ability to manage multiple concurrent projects and priorities.
• Ability to travel up to 20% across the U.S.

Requirements

• 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.
• Experience training users on hardware or connected devices.
• Background in healthcare operations, compliance, quality management, or healthcare IT.
• Familiarity with SCORM/xAPI content standards.
• Experience with accessible, mobile-first, low-bandwidth, and multilingual learning design.

Benefits

• $115,000 – $125,000 base salary.
• 10% annual bonus (not a commission plan).
• 100% company-paid medical coverage (base plan).
• Dental & vision available.
• 401(k) retirement plan.
• Company-paid life, AD&D, STD & LTD insurance.
• Lifestyle Spending Account (wellness, personal use, and company swag).
• Flexible PTO + company holidays.
• Flexible, remote-friendly work environment.
• Mission-driven work with real impact on vulnerable populations.

Company Description

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.