Head of Customer Education

Purple Squirrel Enterprises; Oregon; Hybrid; USD 115,000 - 125,000; Full time

Benefits offered by this job

100% medical coverage

Flexible PTO

Remote-friendly environment

Annual bonus

Job summary

Purple Squirrel Enterprises is partnering with a health tech SaaS client to recruit a Head of Customer Education. This remote, U.S.-based role includes up to 20% travel and potential title changes.

You will own training and certification across the customer base, modernize with a new LMS, and scale through a self-service onboarding model. You will build a small, capable team, design role-based curricula, and partner with Product and Engineering to craft in-platform learning experiences.

Qualifications

• 5+ years in customer education or learning & development in healthcare SaaS.
• Hands-on in creating training materials, guides, videos, and self-serve resources.
• Experience delivering structured training sessions both in person and virtually.
• Experience selecting and implementing an LMS or similar platform.
• Designing certification programs with pass standards and recertification models.
• Proven ability to design and run a train-the-trainer program.
• Leadership experience, with about a year of people management.

Responsibilities

• Lead role-based onboarding for new customers across care settings.
• Deliver live virtual and in-person training tailored to audience.
• Build and manage modular curriculum spanning foundational to advanced topics.
• Create and govern end-user assessments and digital badges.
• Own LMS strategy and data governance for scalable training.
• Design train-the-trainer programs and mentor customer super users.
• Align training outcomes with metrics like NRR, CSAT and health scores.

Skills

Customer education

Training materials

LMS management

Certifications & assessments

Train-the-trainer

Cross-functional collaboration

HIPAA awareness

Tools

LMS

Job description

Head of Customer Education

Location: 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.

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.

About the Role

As part of the Customer Experience team, 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, and earn certification through role-based assessments. Certification here means verified competency on the platform, not restriction, and the goal is to certify as many people as possible. You will own that transition, including bringing in a new learning management system (LMS), adding short-form microlearning (brief videos and assessments) so people can learn the way that works for them, and 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. The role begins with no direct reports, and you will be a player/coach who stays hands-on while building a small team as the function grows.

Training Delivery & Onboarding

• 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

Curriculum Design & Content Development

• 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

Assessments & Certification

• 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

Learning Technology & Data Governance

• 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

Train-the-Trainer, Partnership & Team

• 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

How We Measure Success

KPIDescription Staff Readiness / Assessment Pass Rate% of end users who pass platform assessments on the first or second attempt within the onboarding window Time to CertificationTime from user creation to verified competency Platform & Feature AdoptionAdoption of core workflows after training, including fewer how-to support tickets per active user and uptake of new features within 60 days of launch Training CSATAverage post-training satisfaction (target: 4/5 or higher) Implementation QualityCorrections and rework needed after a customer goes live Trainer Certification Rate% of designated CSMs and Super Users who complete and pass the train-the-trainer program Reach Across Roles and ShiftsAssessment pass rates broken out by role, shift, and site type Content Currency% of training materials updated within the agreed timeframe after a product release or regulatory change

What Success Looks Like

• Training Scales Without Headcount: Most end users are trained, assessed, and certified without a CSM in the room. Live delivery is reserved for facilitated sessions, go-live, and escalation.
• Readiness Is Verifiable: For any customer, at any time, the company can say who is trained, who is certified, and who is overdue.
• Customers Onboard Themselves: Provider organizations bring on new hires using the training program as part of their own onboarding, without reopening an implementation.
• Go-Live Is a Confirmation: Staff arrive at go-live already practiced and already assessed, so launch day validates readiness rather than establishing it.
• Team Excellence: You have built a small, high-performing team that feels supported, coached, and empowered, and the program no longer depends on any one person to deliver it.

What We're Looking ForRequired

• 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)

Preferred

• 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

Compensation & 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

Why This Role — And Why Now

• Real problems, real stakes — your work will help people deliver safe care to vulnerable populations
• A true build — the strategy is defined and has executive backing, while the curriculum, systems, certification program, and team are largely still to be created
• High-growth trajectory — rapid user and program expansion makes this the moment to build for scale
• High-trust, collaborative culture — small team, strong relationships, fast decisions, accessible leadership
• Career growth — high visibility with leadership and a real opportunity to grow a critical function and its team as the company scales
• Authentic mission — this company was built around a cause that matters, and that authenticity permeates everything they do

Our client is an equal opportunity employer committed to building a diverse and inclusive team. They welcome applicants of all backgrounds, experiences, and perspectives.

We are exclusively engaged by this client — meaning we are not one of many agencies submitting resumes. We are their dedicated recruiting partner, embedded in their process, and we know this role inside and out.