If you’re tired of wrestling with CSV uploads or manually tracking who’s taken what training, this guide is for you. Automating user enrollment and group assignments in Skilljar isn’t just about saving time—it’s about keeping your sanity. Whether you’re in customer education, partner enablement, or internal L&D, you need a system that just works. Here’s how to actually get it done, what pitfalls to dodge, and what’s just not worth your energy.
1. Understand What Skilljar Can (and Can’t) Automate
Before you go deep, let’s be clear: Skilljar’s automation features are good, but they’re not magic. The platform gives you a few main ways to automate user enrollment and group assignments:
- Automated enrollments via CSV or SSO integrations.
- Group assignment rules using domains, emails, or custom fields.
- APIs and webhooks for more advanced setups.
But Skilljar isn’t Zapier and it won’t read your mind. If you’re expecting true end-to-end automation with zero setup, you’ll be disappointed.
Key truth: Most organizations end up using a mix of Skilljar’s built-in tools, third-party integrations, and sometimes a bit of manual work. That’s normal.
2. Decide Who Should Be Enrolled (and Why)
Don’t automate just for the sake of it. Figure out who really needs access to what—and when.
- New hires? Maybe you want all new employees enrolled in onboarding modules.
- Customers? You might need to segment by company, subscription level, or product line.
- Partners? Maybe only certain groups get early access to training.
Write this out before you build anything. It’ll save you rework later.
3. Choose Your Enrollment Method
Skilljar supports a few main ways to get users in and into the right groups:
3.1. Manual CSV Upload (The Basic Way)
- Good for: Small orgs, one-time bulk enrollments, or pilot programs.
- How it works:
- Download the Skilljar CSV template.
- Fill in user emails, group names, and course assignments.
- Upload to Skilljar.
- What’s annoying: You have to repeat this every time you add new users. Easy to mess up column names.
Pro Tip: For anything that happens more than once, automate it. Manual CSVs get old, fast.
3.2. Single Sign-On (SSO) and Auto-Provisioning
- Good for: Companies with an existing identity provider (Okta, Azure AD, etc.).
- How it works:
- Connect your IdP to Skilljar using SAML or OAuth.
- Configure attribute mapping—this is how Skilljar knows who should go in which group.
- Users are automatically enrolled (and optionally grouped) the first time they log in.
- What’s tricky: Your IT team will need to help. Attribute mapping is powerful, but easy to misconfigure. Test with a few fake users first.
What to ignore: Don’t bother setting up SSO just for Skilljar if you’re a tiny team. It’s overkill.
3.3. Automated Enrollment Links and Domains
- Good for: Customer or partner training where users self-register.
- How it works:
- Set up unique registration links for different groups or domains.
- Send those links to the right people.
- When someone signs up, Skilljar puts them in the right group automatically.
- Watch out: Links can be forwarded or shared. Not bulletproof if you need tight control.
3.4. Skilljar APIs and Webhooks
- Good for: Large orgs, custom workflows, or when you want to trigger enrollments based on other systems (e.g., CRM, product usage).
- How it works:
- Use Skilljar’s REST API to create users, assign them to groups, and enroll them in courses.
- Set up webhooks to listen for events (like new sign-ups) and trigger actions elsewhere.
- What’s hard: You’ll need a developer or at least someone who can wrangle APIs. Documentation is decent, but not always crystal clear.
Pro Tip: If you’re just starting out, skip the API for now. Try built-in automation first.
4. Set Up Groups and Assignment Rules
Groups are how Skilljar segments users for reporting, permissions, and course access. Get this right early—it’s a pain to fix later.
4.1. Create Groups
- In Skilljar admin, go to Domains & Groups > Groups.
- Create groups that match your real-world needs: “Customers - Enterprise,” “Internal - Sales,” etc.
- Don’t overthink group names; clarity beats cleverness.
4.2. Configure Group Assignment Rules
There are a few main ways to assign users to groups automatically:
- By email domain: Anyone registering with
@acme.comgoes into the “Acme Customers” group. - By registration link: Each link ties to a specific group.
- By custom user fields: If you’re importing via API or CSV, set a custom field (like “Department: Sales”) and use that for grouping.
What doesn’t work: Skilljar won’t let you stack rules (e.g., “If domain is X and custom field is Y”). Keep it simple.
5. Automate Enrollment into Courses and Learning Paths
Once users are in the right groups, you want them enrolled in the stuff they need—without you hand-holding every time.
5.1. Auto-Enrollment by Group
- In the course or learning path settings, set up auto-enrollment rules based on group membership.
- Example: “All users in ‘Partners - Tier 1’ get enrolled in ‘Partner Onboarding’ automatically.”
- Double-check that notifications are set up so users know they’ve been enrolled.
Pro Tip: Start with “view only” access if you’re nervous about flooding users’ inboxes.
5.2. Scheduled Enrollment
- Skilljar can schedule enrollments for a future date, but it’s not deeply flexible.
- Good for rolling out training in cohorts.
- Not so great if you need sophisticated drip campaigns.
6. Test Everything (Seriously)
Before you go live, create a few test users and walk through the process yourself.
- Register using different emails/domains.
- Check group assignments and course enrollments.
- Make sure welcome emails and notifications work.
- Delete test data when you’re done.
What to ignore: Don’t assume “it’ll just work” because you set up a rule. Skilljar is powerful, but not always forgiving of typos or misconfigured fields.
7. Maintain and Monitor
Automation isn’t set-and-forget. Review your groups and enrollments every quarter (or more if things change fast).
- Check for inactive users and clean them out.
- Review auto-enrollment rules after org changes.
- Spot-check course access to make sure nothing weird is happening.
If you’ve got a lot of turnover (customers, partners, staff), consider syncing user lists with your HRIS or CRM via API.
Honest Take: What Works, and What’s Overhyped
What’s great: - SSO and domain-based group assignments save a ton of time once set up. - Auto-enrollment by group keeps new hires and customers from falling through the cracks.
What’s just okay: - CSV uploads are fine for now-and-then, but get old quick. - APIs open up lots of options, but only if you have dev resources.
What’s not worth it: - Over-engineering your group structure. The more rules, the more things break. - Trying to automate everything from day one. You’ll burn out.
Wrapping Up: Keep It Simple, Iterate Often
Start with the basics—get your groups and auto-enrollments working, then layer on more automation as your needs get clearer. Don’t waste time on edge cases until your main flows work every time. The best automation is the kind you almost forget is running. If you’re spending all day fiddling with Skilljar settings, it’s time to take a step back.
Need help? Start simple, get feedback, and make changes as you go. No need to chase perfection—just aim for fewer headaches.