The Customer Education LMS Evaluation Playbook
Download our RFP Template
It’s time to turn this playbook into action. Our editable template helps you capture business context, prioritize Table Stakes vs. Strategic Enablers, and align IT/procurement so vendors can deliver tailored proposals, making it easier for you to compare apples to apples.
LMS Evaluation Has Changed — Here’s What to Know
Customer education has become a critical growth lever. The right learning platform directly impacts onboarding speed, product adoption, customer retention, and ultimately revenue growth. As I often remind executives I work with: “Your LMS is not just a delivery system, it’s an engine for customer outcomes.”
But the way buyers approach LMS evaluation is shifting. The old model of checking off feature boxes is giving way to a new mindset: buying outcomes tied to business strategy.
As Eric Mistry, CSM & Automation Transformation Lead at Zapier and writer of the Customer Education Bi-Weekly newsletter, put it:
This playbook is designed as a strategic guide for customer education and digital success leaders, LMS admins, and executives alike. It positions LMS evaluation not as a tactical exercise, but as a roadmap to measurable CX outcomes. I developed this playbook in collaboration with Skilljar after analyzing hundreds of RFPs from real customers and speaking with leading Customer Education (CE) experts. It brings together those insights with my own best practices from building and scaling education programs at large, complex enterprise organizations.
As you read, use the accompanying Customer Education RFP Template to capture your business context and translate strategy into an actionable evaluation plan.
Why Executives should care about Education
Customer education has evolved from a support function to a strategic growth driver. According to TSIA’s 2025 Education Services as a Product and a Growth Driver report, leading organizations are adopting an education-led growth (ELG) framework that aligns customer learning programs directly with core business outcomes such as revenue, retention, and product adoption. In this new model, success depends on executive alignment — ensuring education is measured, funded, and prioritized as a driver of business results.
Before evaluating features or vendors, align at the executive table on what outcomes education must deliver for the business. The right LMS is a growth lever, an efficiency driver, and a future-proofing hedge.
Below are the metrics your executives actually care about. Each is tied to measurable metrics, common use cases, and long-term strategic considerations. For a broader perspective, I recommend this conversation between Adam Avramescu and Dee Kapila — two leading voices in digital CX — which offers an overview of the metrics executives prioritize when it comes to customer experience. Listen to the podcast here.
Why it matters
The faster customers achieve first value, the faster they become sticky, referenceable, and ready to expand. Delays in onboarding directly erode trust and ARR.
Metrics
Time to first login, time to feature adoption, time to value milestones.
How Education supports this outcome:
Structured onboarding pathways, role-based starter guides, guided activation experiences in-app.
What to look for as you grow
Make sure your LMS can handle onboarding in different contexts — from product-led growth motions where you’re serving thousands of self-serve users, to highly segmented enterprise audiences, to global rollouts that require multilingual support and regional compliance. The right platform should flex with your business model, not force you into one way of onboarding.
Recommendation
Use product telemetry data such as feature clicks, usage patterns and heatmaps to define what “first value” looks like for your customers, then validate it through experiments.
Why it matters
Expansion and retention depend on customers using more of the product they’ve already purchased. Education bridges the gap from license to usage.
Metrics
Feature adoption rates, active usage frequency, breadth/depth of adoption across roles, expansion revenue.
How Education supports this outcome:
Product training libraries, in-app nudges, feature-specific tutorials, contextual video support.
What to look for as you grow
Look for an LMS that integrates seamlessly with your product and data stack so you can deliver education in-app and personalize learning paths based on actual usage. Without deep integrations, personalization and timely adoption campaigns simply won’t scale.
Recommendation
Confirm the vendor’s roadmap supports in-product delivery and analytics-based personalization.
Why it matters
Renewals and expansions are strongest when customers are competent, confident, and capable of proving ROI internally. Education lays the foundation for advocacy and expansion.
Metrics
Renewal rates, NDR, expansion %, customer health scores.
How Education supports this outcome:
Continuing education programs, upskilling pathways, certifications, and role-based enablement (e.g., for admins).
What to look for as you grow
Choose an LMS that connects learning data to your customer success platform so you can clearly track how education influences adoption, health scores, and renewals. Without that link, education risks being undervalued in renewal conversations.
Recommendation
Ensure your LMS analytics can integrate with Gainsight CS or similar systems so you can demonstrate a clear line from learning to retention.
Why it matters
Customer education is a recognized growth driver, driving certification revenue, training subscriptions, and pipeline influence.
Metrics
Certification revenue, training subscription revenue, pipeline contribution.
How Education supports this outcome:
Paid certification programs, premium course packages, partner enablement programs, and education-driven marketing campaigns.
What to look for as you grow
Make sure your LMS supports flexible monetization models — from ecommerce and subscriptions to partner marketplaces. As programs scale, you’ll need global payment options, tax compliance, and reporting that ties education to pipeline influence.
Recommendation
Validate that your LMS can handle ecommerce at scale and supports the partner distribution models relevant to your GTM strategy.
Why it matters
Educated customers are more confident, satisfied, and willing to champion your product. Advocacy doesn’t just boost NPS scores — it fuels case studies, reference calls, and community activity that reduce CAC and accelerate sales cycles.
Metrics
NPS, CSAT, referenceable customers, community contributions, advocacy-driven pipeline.
How Education supports this outcome:
Integrated learning + community journeys, recognition badges, and certification programs that build credibility while inspiring customers to share their success stories.
What to look for as you grow
Seek a platform that integrates seamlessly with your community and advocacy tools. This ensures learning milestones can trigger recognition, engagement, and customer storytelling at scale.
Recommendation
Build advocacy into your education strategy from the start. Treat certifications, communities, and recognition programs not just as learning outputs, but as engines for customer voice and brand amplification.
Why it matters
Education reduces reliance on high-cost human touch. For SaaS companies, that often means freeing CSMs to focus on strategic accounts while enabling global reach without ballooning headcount. For CFOs, this is the most tangible ROI case.
Metrics
Tickets deflected, CSM-to-customer ratio, cost per customer, global/local coverage.
How Education supports this outcome:
Multilingual programs, localized experiences, role-based learning at scale, and just-in-time self-service.
What to look for as you grow
Ensure the LMS can support global expansion, complex identity management, delegated admin, and licensing models that flex as your audiences grow. The right platform should help you scale without adding headcount.
Recommendation
Treat your LMS as a force multiplier. The more it automates routine training and support, the more your high-value teams can focus on strategic growth activities.
Taken together, these six outcomes show how education strategy should flow into execution. This is where many RFP processes go wrong: they jump straight to feature checklists instead of asking how features connect to strategy. By explicitly mapping Objectives → Use Cases → Product Capabilities, you create a direct line from business priorities to system requirements. But even the strongest business case will stall if you don’t have the right champions at the table. That’s why the next step is aligning cross-functional stakeholders — and showing each of them what’s in it for them.
Download our RFP Template
It’s time to turn this playbook into action. Our editable template helps you capture business context, prioritize Table Stakes vs. Strategic Enablers, and align IT/procurement so vendors can deliver tailored proposals, making it easier for you to compare apples to apples.
Cross-Functional Alignment
One of the biggest risks in LMS evaluation is treating it as a siloed project owned only by Customer Education or L&D. The most successful programs are shaped by — and accountable to — multiple stakeholders. To earn buy-in, you need to show each function how the LMS directly helps them achieve their goals. Often, this comes down to the integrations that unlock value for their teams.
Cross-Functional Alignment
Customer Success & Support
An LMS takes routine training off their plate, so they can focus on strategic relationships, high-value accounts, and true advisory work. In short: your LMS should be your CSMs’ MVP.
IT & Security
Standard integrations, SSO, and compliance controls reduce workload, mitigate risk, and keep governance simple.
Executive Leadership (CEO/CFO/COO):
Education is a measurable growth lever. It accelerates time-to-value, drives NRR, and improves efficiency. For CFOs in particular, it helps consolidate vendors, reduce support costs, and even unlock new revenue streams. (See CFO Buy-In Letter for a template you can adapt when making your case.)
Product & Engineering
Training data highlights where users succeed and where they struggle, giving product teams direct insight into adoption barriers and feature opportunities.
Marketing & Community
Certifications and learning journeys create new storytelling assets, fuel advocacy, and increase engagement across community channels.
Best practice: Build a cross-functional steering committee before starting your evaluation, and use the Customer Education RFP Template as a shared workspace to gather stakeholder input. Each tab gives key functions a space to capture their priorities, ensuring alignment, faster buy-in, and a smoother selection process.
Vendor Differentiation & Evaluation Criteria
On paper, most vendors look similar. The real difference emerges in how well a platform supports your objectives, scales with your business, and delivers value over time. To make sense of the landscape, it helps to understand the three main categories of LMS:
Internal LMS: Built for employee training, compliance, and workforce development. Strong for HR needs, but they fall short for external education — lacking customer-facing SSO, branding, ecommerce, advanced analytics, and multi-audience personalization.
External LMS: Purpose-built for customers, partners, and other external audiences. These systems prioritize usability, branding, and scalability to meet customer expectations and integrate more deeply with business systems, such as Salesforce and Customer Success Platforms. They’re designed to drive adoption, retention, and revenue.
Hybrid / All-in-One LMS: Flexible platforms that aim to serve both employees and external audiences. They can cover more ground, but often at the expense of specialization, leaving them as generalists rather than best-in-class solutions.
For customer education teams, external LMS platforms like Skilljar by Gainsight are optimized to deliver business impact across the entire customer lifecycle — from onboarding to advocacy — making them a stronger fit than internal or hybrid systems.
Still, category is only part of the equation. The real filter is how well an LMS fits into your existing tech stack and the scale of your customer base. A company running HubSpot CRM with 2,000 monthly learners will have different requirements than one running Salesforce with 10,000 learners. At the end of the day, it’s not just about whether a platform can “integrate,” but whether it can share the right data with the right systems to drive outcomes at scale.
Table Stakes (Core Capabilities)
Multi-format content hosting & delivery (SCORM, xAPI, LTI 1.3, video, docs, interactive modules):
Ensures you can support diverse learning modalities and industry standards and easily import content authored in tools like Articulate, Captivate, or Parta.io without costly workarounds.
User & group management with role-based permissions
Critical for segmenting learners by customer, partner, or role and controlling access appropriately.
Assessments, certification management, and progress tracking
Fundamental to measuring learner competency, proving ROI, and creating structured pathways.
Reporting & analytics
Provides visibility into usage and outcomes for both admins and executives — a baseline expectation.
Standard integrations (CRM, Customer Success Platform, SSO, web conferencing, etc)
Reduces login friction, increases adoption, and enables alignment with enterprise systems.
Administrative ease of use
If admins can’t easily configure and manage the system, programs stall. A must-have for scalability.
Note: These capabilities only matter if they tie directly to your objectives and use cases. For example: if your goal is certification revenue, ecommerce is a must-have. If you’re scaling partner enablement, multi-audience support becomes critical. If you want to boost engagement and advocacy, recognition tools and campaigns make the difference. The key is mapping outcomes → use cases → capabilities, not chasing shiny features that don’t serve your strategy
Strategic Enablers (Advanced Capabilities)
Personalization & Adaptive Learning
Dynamically show the right learning to the right person at the right time—by account, role, product plan, region, lifecycle stage, or usage signals.
Multi-Tenant/Multi-Audience
Delivers distinct experiences for customers, partners, and business units within one platform — essential for scaling external education.
Branding & White-Labeling
Advanced theming/white-labeling, per-audience branding, custom domains, and flexible navigation so the academy feels like part of your product.
Engagement & Campaigns
Completion nudges and re-engagement campaigns that keep learners progressing toward desired outcomes. Integrates with your ESP/MA tool for robust orchestration.
In-Product Delivery & Embeds
Surface learning inside your product, community, or docs via SDKs/widgets/deep links—with progress tracking and SSO preserved.
Badging & Certification
Robust cert lifecycle (issuance, expiry, re-cert), proctoring integrations, CE/CPE credit tracking, LinkedIn sharing.
Commerce & Monetization
Subscriptions, bundles, coupons, corporate invoicing/PO, taxes/VAT, multi-currency, and entitlements—plus revenue and utilization reporting by account.
API extensibility & workflow integration
Ensures the LMS can connect into broader CX workflows, such as automatically updating CRM or CS platforms when a learner completes training.
Localization & Accessibility at Scale
Translation management, multi-locale catalogs and certificates, right-to-left support, and WCAG compliance. Necessary for global programs and enterprise procurement.
What it actually means: True headless means the LMS is stripped of its own front-end, serving purely as a content repository and data engine. Your team, assuming you have developer resources, builds and maintains a fully custom front-end experience on top of it. In theory, this gives more flexibility because it’s API-driven. In practice, it also means you own long-term upkeep, testing, and governance.
When it makes sense: Rarely. Typically, only for companies with major engineering resources that want to control every aspect of the learner experience — and can absorb the cost and complexity. Even with vibe-coding AI tools to speed up UI development, integration logic, security policies, and compliance tracking remain high-stakes
Where confusion happens: Many teams say “headless” when what they actually mean is integration — embedding courses into an app, portal, community or other digital surface. Most of these use cases can be achieved without going fully headless.
What to look for instead: Focus on extensibility. Robust APIs, widgets, embeds, SDKs, and syndication tools give you 95% of the flexibility you need — while still leveraging the LMS front end. This lets you surface learning wherever customers are without taking on the burden of building and maintaining your own platform.
Bottom line: Headless = build the entire LMS front-end yourself, while integration = extend the LMS front end into other surfaces. Headless sounds innovative, but in most cases it’s a distraction from the real question: Can this LMS integrate deeply enough to deliver the seamless, branded, personalized experiences we need?
Future-Proofing Considerations
Once you’ve confirmed table stakes and advanced capabilities, the final question is whether the LMS can grow with you. Future-proofing is about choosing a platform that won’t just solve today’s needs, but will still be relevant as your customer base, team, and tech stack evolve.
AI Readiness: Don’t stop at course creation. True AI maturity spans three dimensions:
- AI for admins: Automating course creation, tagging, content improvement, and analytics so teams scale without adding headcount.
- AI for learners: Powering role-based recommendations, personalized pathways, and contextual support (chat/tutor) that meet customers where they are.
AI for your ecosystem: Interoperating with the rest of your stack — Customer Community, PX, CS tools, and third-party authoring platforms — to create seamless, orchestrated journeys.
Analytics Maturity: Reporting shouldn’t just count course completions. It should connect learning activity to adoption, retention, expansion, and advocacy, and integrate into BI tools for enterprise visibility.
Ecosystem Fit: Beyond “does it integrate,” ask whether the LMS can share the right data with CRM, CS tools, community, and marketing automation platforms. Weak data flows create silos that block business impact.
Scalability & Governance: As you grow, ensure the platform supports global expansion, flexible licensing, enterprise-grade compliance, accessibility (WCAG), and localization at scale.
Vendor Credibility & Brand Proof: A vendor’s own academy, community, and knowledge base are signals of their maturity. Danielle Evans (Sendoso) emphasized: “Do they walk the talk? If they can’t educate their own customers, how will they help you educate yours?”
Pro tip: “Don’t just evaluate features — push vendors to connect their roadmap to your business strategy.”
Samantha Murray
Download our RFP Template
It’s time to turn this playbook into action. Our editable template helps you capture business context, prioritize Table Stakes vs. Strategic Enablers, and align IT/procurement so vendors can deliver tailored proposals, making it easier for you to compare apples to apples.
Risks & Red Flags
Selecting an LMS is often less about the “shiny demo” and more about uncovering the gaps that emerge in real-world usage, migration, and scale. Leaders consistently flagged where evaluations fall short — and where programs run into hidden risks. To keep this practical and scannable, here are the most common red flags:
Over-Customization & False Differentiation
Integration Gaps
Migration Pitfalls
Governance & Access Control Gaps
Hidden Costs
Weak Roadmap Alignment
As Kristin Thompson (VAST Data) put it: “If it’s not shipping in the next two months, assume it’s a pipe dream.”
Shiny Demo Syndrome
Procurement Readiness
Selecting the right LMS is only half the battle. Procurement is often the least exciting part of the journey — but the more prepared you are, the faster you’ll move through it and get to value. Preparation matters because it reduces IT and Legal bottlenecks, speeds up budget approvals, and keeps your rollout timeline on track.
Budget Ranges & Pricing Models
LMS pricing varies widely, from per-user or per-active-user models, to per-portal or enterprise-wide licenses. Beyond the license, anticipate additional costs for integrations, migration services and ongoing vendor support. If you want to dig deeper into pricing structures and Active User models, Skilljar has a helpful FAQ on LMS pricing.
Best practice: Build a 3-year cost model that accounts for growth, new use cases, and potential expansion to partners or global audiences. And be ready for the CFO question: “Why can’t we just use our existing internal LMS?” This is where you’ll need to show the gaps we covered earlier — internal LMSs are built for employees, not customers. They lack customer-facing SSO, ecommerce, advanced analytics, and multi-audience personalization — all essential for customer education at scale.
Change Management & Implementation Alignment
Planning for change during the evaluation stage prevents rollout delays and ensures adoption. Teams that wait until after purchase often struggle with unclear ownership, resistance, and missed deadlines.
Best practice: Define the change narrative, assign clear owners early, and plan a phased rollout with quick-win milestones to build momentum and alignment.
Timeline Expectations
While vendors often promise “quick deployment,” real-world implementations typically span 3–6 months, and up to 12 months for large, complex enterprise use cases. Timelines are driven by factors such as migration complexity, integration testing, and pilot launches with feedback cycles before global rollout.
Best practice: Treat deployment as a phased rollout — start with a core use case or audience, gather feedback, and then expand.
Procurement Process & Governance
Procurement requires alignment across multiple functions, and skipping this step is the fastest way to stall your project. Each group will surface its own requirements and concerns — from security reviews to contract terms — so it’s critical to bring them in early.Security & IT: Compliance standards such as SOC2, GDPR, data residency, and role-based access.
- Security & IT: Compliance standards such as SOC2, GDPR, data residency, and role-based access.
- Legal: Contracts, SLAs, liability, and privacy policies.
- Finance/Procurement: Budget approval, vendor risk assessment, and cost justification.
RFP Template
Final Recommendations: How to Use This Playbook and RFP Template
Align leadership on objectives first
Anchor your evaluation in measurable executive outcomes — onboarding, adoption, retention, revenue, advocacy, and efficiency. Use the Company & Team Context tab in the RFP Template to document your organization’s priorities and KPIs.
Form a cross-functional steering group
Don’t evaluate in a silo. Involve CS, Support, Product, IT, Security, Marketing, and Finance early to shape requirements and smooth procurement. Use the RFP Template as a shared workspace to capture each team’s input and priorities.
Select features and criteria based on objectives, not checklists.
Use the cascade from objectives → use cases → jobs-to-be-done → capabilities to identify what really drives value.
Engage stakeholders early in the procurement process
Share your draft requirements with IT, Legal, and Procurement early. This prevents late-stage roadblocks and accelerates contracting and onboarding.
Treat this as both a procurement tool and a strategic roadmap
The playbook helps you think through the “why” behind your education strategy; the RFP Template helps you operationalize the “how.” Together, they form a complete framework for evaluating vendors, aligning stakeholders, and scaling your customer education program.
What sets Skilljar apart is that it’s the only LMS purpose-built to integrate education seamlessly into the broader Customer OS — alongside Customer Success, Product Experience, and Community. This isn’t about education in a silo, it’s about education as a growth engine embedded across the entire customer lifecycle.
“Education is not an island — it’s the connective tissue of your customer journey.”
If you found this playbook helpful, I’d love to hear about it! Find me on LinkedIn and drop me a line.
Until next time,
Samantha Murray
Founder & CEO
AlignedCX
About Samantha Murray
Samantha Murray is the Founder and CEO of AlignedCX, a strategic advisory firm helping B2B software and AI companies turn customer experience into a growth engine. With over a decade in go-to-market and customer experience leadership at Shopify and Docebo, Samantha brings a unique perspective shaped by being both a buyer and builder in the learning technology ecosystem. Today, she advises CX executives on how to design intelligent systems, aligned customer journeys, and scalable digital experience strategies that drive retention and expansion.