Head of Customer Education

Purple Squirrel Enterprises • Baltimore, MD

9d • $115,000 - $125,000 • Remote

About The Position

The Head of Customer Education will own training and certification across the customer base, ensuring customer teams are trained, operationally prepared, and able to achieve lasting value from the platform. This is a hands-on foundational role within the Customer Experience team, responsible for moving training from a largely instructor-led model to a self-service-first model planned for 2027. The transition includes selecting and implementing an LMS, introducing short-form microlearning, developing role-based assessments and certifications, and partnering with Product and Engineering on in-platform learning.

The role supports state program partners, enterprise accounts, and commercial customers in IDD, behavioral health, and long-term care settings. Learners may have limited technical confidence and work in high-turnover, regulated care environments. The successful hire will deliver training while building scalable curricula, content, assessment systems, data governance, and train-the-trainer programs. The role starts with no direct reports and is expected to build a small team as the function grows.

The position is fully remote and U.S.-based, aligned to East Coast hours, with travel of up to 20% across the U.S. The stated base salary is $115,000–$125,000, plus a 10% annual bonus.

Requirements

• At least 5 years of experience in customer education, training, enablement, or L&D, including designing and delivering curricula for end users of a healthcare SaaS platform.
• Hands-on experience creating training materials such as presentations, job aids, help documentation, video walkthroughs, and self-service learning resources.
• Experience conducting structured training sessions both in person and virtually.
• Familiarity with adult learning principles and instructional design methodologies such as ADDIE and Kirkpatrick.
• 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; approximately one year of people leadership may be considered with clear aptitude to lead.
• Experience in a highly regulated environment and a strong understanding of healthcare documentation standards and compliance-driven workflows, including HIPAA-aware handling of training data.
• Strong data orientation and experience tying learning outcomes to retention, satisfaction, or health-score measures.
• Excellent written and verbal communication, including the ability to translate complex workflows into clear guidance for users with varied levels of technical comfort.
• Ability to manage concurrent projects and priorities in a fast-moving startup environment.
• Ability to travel up to 20% across the U.S. for on-site customer training and onboarding.
• Must be U.S.-based and able to work East Coast hours; West Coast candidates should expect some early mornings and early meetings.

Nice To Haves

• 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.

Responsibilities

• Lead role-based end-user onboarding for new customers across IDD, behavioral health, and long-term care settings.
• Deliver live virtual and in-person training tailored to frontline staff, program managers, administrators, clinical leads, and executives.
• Run a scheduled, facilitated virtual training program as an ongoing service.
• Provide multiple learning paths to the same competency so differences in role, shift, or technology comfort do not prevent success.
• Design continuous onboarding to account for customer staff turnover and new hires arriving after implementation.
• Design a tiered, role-based curriculum covering foundational training, role- and device-based workflows, go-live readiness, and ongoing education.
• Create and maintain presentations, facilitator guides, job aids, help articles, FAQs, on-demand modules, video walkthroughs, and guided click-throughs.
• Build a modular content library that supports universal, state-specific, and customer-specific programs without maintaining parallel content sets.
• Partner with Product to prepare training for feature launches and update materials when regulations, workflows, or product functionality change.
• Develop end-user assessments that measure role-specific readiness.
• Design skill-level certifications and role-level credentials that build on those certifications.
• Define assessment standards and processes, including pass thresholds, retries, role gating, expiration, and recertification cadence.
• Launch verifiable digital badges and maintain accurate, timestamped, auditable assessment and certification records.
• Evaluate, select, and own the LMS and other tools needed for a scalable training program.
• Partner with Product and Engineering on the in-platform learning experience and scalable training infrastructure.
• Own training-data governance, including data visibility throughout the learner journey, access, and safeguards.
• Partner with Compliance, Privacy, and Legal on HIPAA-appropriate training-data handling, using synthetic or de-identified data where real data is unnecessary.
• Design and lead a train-the-trainer program for CSMs.
• Certify and coach customer Super Users to become internal training leads.
• Share recurring learner confusion and support-ticket themes with Product as roadmap input.
• Work with CSMs to assess customer readiness, identify adoption gaps, and deliver training at implementation and go-live milestones.
• Build a network of subject matter experts across CSM, Support, and Product to review content accuracy regularly.
• Own the KPI framework connecting training outcomes to NRR, CSAT, renewal rate, NPS, and customer health score, and establish baselines.
• Partner with the Chief Customer Officer to hire and develop a small team, including regular one-on-ones, performance reviews, development plans, and coaching.

Benefits

• 100% company-paid medical coverage for the base plan.
• Dental and vision coverage available.
• 401(k) retirement plan.
• Company-paid life, AD&D, short-term disability, and long-term disability insurance.
• Lifestyle Spending Account for wellness, personal use, and company swag.
• Flexible PTO and company holidays.
• Flexible, remote-friendly work environment.
• Competitive base salary of $115,000–$125,000 and a 10% annual bonus.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed