Head of Customer Education

Purple Squirrel Enterprises•Baltimore, MD

7d•Remote

About The Position

The Head of Customer Education will own training and certification across the customer base, ensuring customers’ teams are trained, operationally prepared, and able to get lasting value from the platform. This is a foundational, hands-on build role within the Customer Experience team. Training is currently delivered largely by people, and the company plans to move to a self-service-first model in 2027. The role will lead that transition by establishing structured onboarding, a safe practice environment, role-based assessments and certification, a new learning management system (LMS), microlearning, and an in-platform learning experience developed with Product and Engineering. The role serves state program partners, enterprise accounts, and commercial customers in IDD, behavioral health, and long-term care settings. Learners may have limited technical comfort and work in high-turnover, regulated care environments. The role will provide live virtual and in-person training while building scalable self-service and continuous-onboarding programs. It starts without direct reports; the successful hire will initially be a hands-on player/coach and build a small team as the function grows. The position is fully remote and U.S.-based, with East Coast working hours and travel of up to 20% across the U.S. The role reports to the Chief Customer Officer. The advertised title is Head of Customer Education; the final title and compensation will reflect the hire’s experience and level. Compensation is $115,000–$125,000 base salary plus a 10% annual bonus.

Requirements

At least 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 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 strong understanding of healthcare documentation standards and compliance-driven workflows, including HIPAA-aware handling of training data.
Strong data orientation and experience connecting 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 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. 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, and provide multiple paths to competency for learners with different roles, shifts, and levels of technical comfort.
Design for continuous onboarding so new staff can be trained after implementation, accounting for high turnover.
Design a tiered, role-based curriculum covering foundational training, role- and device-based workflows, go-live readiness, and ongoing lifecycle education.
Build and maintain instructor-led presentations, facilitator guides, job aids, help articles, FAQs, on-demand modules, video walkthroughs, and guided click-throughs.
Create a modular content library for universal, state-specific, and customer-specific programs without maintaining parallel content sets.
Partner with Product to prepare training for new feature launches and proactively update materials when regulations, customer workflows, or product functionality change.
Develop end-user assessments that measure readiness against each role’s responsibilities, and design skill-level certifications and role-level credentials.
Define assessment and certification policies, including pass thresholds, retry rules, role gating, expiration, and recertification cadence.
Launch verifiable digital badges and ensure assessment and certification records are accurate, timestamped, and auditable.
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 training infrastructure.
Own training data governance, including what learner data appears at each stage, who can access it, and what safeguards apply.
Partner with Compliance, Privacy, and Legal on HIPAA-appropriate handling of training data, using synthetic or de-identified data wherever real data is not required.
Design and lead a train-the-trainer program so CSMs can deliver consistent training to their accounts; certify and coach customer Super Users to train their organizations’ new hires.
Bring recurring learner confusion and support-ticket themes to 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 linking 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 1:1s, performance reviews, development plans, and coaching.
Measure and improve staff assessment pass rates, time to certification, platform and feature adoption, training CSAT, implementation quality, trainer certification rates, reach across roles and shifts, and content currency.
Build a scalable program so most end users can be trained and certified without a CSM present, customers can onboard new hires themselves, and readiness can be verified at any time.

Benefits

$115,000–$125,000 base salary plus a 10% annual bonus.
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.
Mission-driven work with real impact on vulnerable populations.
Career growth and the opportunity to build a critical function and its team as the company scales.