[Remote] Head of Customer Education

Note: The job is a remote job and is open to candidates in USA. Purple Squirrel Enterprises is recruiting on behalf of an unnamed high-growth health technology company. The Head of Customer Education will build and lead a scalable customer training and certification program, including onboarding, curriculum, learning technology, assessments, and partnerships across customer-facing and product teams.

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 the audience: frontline staff, program managers, administrators, clinical leads, and executives
• Run a scheduled, facilitated virtual training program as a standing service rather than one-off sessions
• Offer more than one path to the same competency, so role, shift, and comfort with technology do not decide who succeeds
• Design for continuous onboarding: turnover is high, and new staff arrive long after an implementation has closed
• Design a tiered, role-based curriculum spanning foundational training for all users, role- and device-based workflow training, go-live readiness, and ongoing lifecycle education
• Build and maintain training materials, including instructor-led presentations, facilitator guides, job aids, help articles, FAQs, on-demand modules, video walkthroughs, and guided click-throughs
• Build a modular content library that assembles into universal, state-specific, and customer-specific programs without maintaining parallel content sets
• Partner with Product so training is ready at launch for new features, and update materials proactively when regulations, customer workflows, or product functionality change
• Build end-user assessments that measure readiness against what each role actually does
• Design skill-level certifications mapped to specific workflows, and role-level credentials that roll up from them
• Define the assessment model, including pass thresholds, retry rules, role gating, expiration, and recertification cadence
• Launch verifiable digital badges that staff can carry into their own careers
• Ensure assessment and certification records are accurate, timestamped, and auditable
• Evaluate, select, and own the LMS and tooling needed for a scalable training program
• Partner with Product and Engineering on the in-platform learning experience and on training infrastructure that supports rapid user growth without sacrificing quality
• Own the data governance model for training: what data appears at each stage of the learner journey, who can reach it, and under what safeguards
• 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. Everyone here is responsible for protecting PHI
• Design and lead a train-the-trainer program that enables CSMs to deliver consistent, confident training to their accounts
• Certify and coach customer Super Users to serve as internal training leads, so customer organizations can onboard their own new hires over time
• Bring recurring learner confusion and support ticket themes back to Product as roadmap signal
• Work with CSMs to assess customer readiness, spot 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 on a regular cadence
• Own the KPI framework linking training outcomes to NRR, CSAT, renewal rate, NPS, and customer health score, and set the baselines needed to show that link over time
• Partner with the Chief Customer Officer to hire and develop a small team, with regular 1:1s, performance reviews, development plans, and coaching

Skills

• 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
• 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
• 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

Benefits

• 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

Company Overview