If you’ve ever tried to get new customers up and running in a SaaS product, you know how messy onboarding can get. Too many emails, too many manual steps, and way too many people “falling through the cracks.” If you’re looking for a way to actually automate onboarding—not just send more reminders—this guide is for you. We’ll walk through using Endgame, a tool built to automate customer workflows, and cover what works, what doesn’t, and how to keep your setup from turning into a mess.
Why automate onboarding anyway?
Let’s be real: manual onboarding is slow, inconsistent, and usually annoying for everyone involved. Automating onboarding isn’t about “scaling” so much as not losing your mind (or your customers) to repetitive, easy-to-mess-up tasks.
Benefits worth caring about: - Customers get to value faster, which means fewer drop-offs. - Your team stops spending time chasing signatures or answering the same basic questions. - You can spot when someone’s stuck—and actually do something about it.
But here’s the catch: it’s easy to overcomplicate things and wind up with a Rube Goldberg machine nobody understands. The trick is to automate what’s predictable and keep a human touch where it actually matters.
Step 1: Map out your onboarding workflow—before touching Endgame
You don’t need fancy tools to start. Grab a whiteboard, spreadsheet, or even a notebook. Lay out every step a new customer takes from “just signed up” to “fully onboarded.” Be brutally honest.
Typical steps might include: - Welcome email sent - Account setup by customer - Key integrations connected - First project or action completed - Training session scheduled (if needed) - First success metric hit
Pro tip: Write down who’s responsible for each step (customer, your team, or both). Mark where things often break down or get delayed. Don’t skip this part—if you can’t draw your process, Endgame can’t automate it.
Step 2: Get familiar with Endgame’s basics
Endgame is designed for automating post-sale workflows, especially onboarding and expansion. It connects to your CRM (Salesforce, HubSpot, etc.), product analytics (Mixpanel, Amplitude), and communication tools (Slack, email, whatever you use).
The core pieces: - Workflows: The automation “recipes” that move customers through steps. - Triggers: The event that starts a workflow (new deal closed, trial started, etc.). - Actions: What Endgame actually does (send an email, assign a task, update a field). - Milestones: Key points in the journey (first login, integration completed, etc.). - Playbooks: Collections of best-practice workflows.
Don’t let the terminology scare you. Most of it’s just “if X happens, do Y.” But it’s worth poking around in a sandbox account or demo to see how it all clicks together.
Step 3: Connect your core data sources
Automated onboarding lives or dies on the data you feed it. Connect the essentials first:
- CRM (Salesforce, HubSpot, etc.): Where your customer/account records live.
- Product analytics (Mixpanel, Segment, Amplitude): Tracks what users actually do.
- Communication tools (email, Slack): How you or Endgame will nudge folks.
- Support tools (Zendesk, Intercom): Optional, but useful to trigger help when customers get stuck.
What to skip: Don’t connect every tool under the sun “just in case.” More connections = more headaches when something breaks.
Gotcha: If your product analytics doesn’t track key onboarding actions (like “integration connected”), fix that first. No tool can automate what you can’t measure.
Step 4: Build your first onboarding workflow
Now the fun part. Start simple—don’t try to automate the whole journey out of the gate.
Example: First integration connected
Let’s say your onboarding hinges on customers connecting an integration (like Slack or Salesforce). Here’s how you might automate it:
- Trigger: New customer hits “signed” in your CRM.
- Action: Endgame sends a personalized welcome email with a clear CTA to connect the integration.
- Wait & Listen: Endgame checks your product analytics every few hours—did the customer connect the integration?
- Branch:
- If yes: Send a “nice work!” email and assign a CSM to schedule a call.
- If not after 3 days: Auto-send a friendly nudge with a link to help docs.
- Escalate: If still nothing after a week, create a task for a human to reach out directly.
Pro tip: Always set a human fallback. Automation is great until it isn’t—don’t let customers get lost in a loop of automated emails.
Step 5: Add milestones and track progress
Milestones are your “are we there yet?” checkpoints. Set these up for the key moments you care about—first login, first project created, integration connected, etc.
- Use Endgame’s milestone tracking to visualize where each customer is in real time.
- This isn’t just for show: it helps your team spot who’s stuck and jump in before it’s too late.
What to ignore: Don’t go overboard with 15 different milestones. Focus on the 3-5 that actually predict success.
Step 6: Layer in playbooks for repeatable processes
If you have multiple onboarding tracks (e.g., different flows for SMB vs. enterprise), use Endgame’s playbooks. These are templates for common workflows.
- Start with what Endgame provides out of the box, but tweak to fit your real process.
- Don’t try to “templatize” everything—custom work is unavoidable for big accounts.
Honest take: Playbooks save time, but they’re not magic wands. You’ll still need to keep things updated as your process changes.
Step 7: Set up alerts and handoffs
Automation is great, but you’ll always need humans for edge cases. Use Endgame to:
- Alert CSMs or onboarding specialists when a customer is stuck on a milestone.
- Assign tasks automatically when manual steps are required.
- Pipe critical events into your team’s Slack or email—just don’t overdo it or everyone will ignore the alerts.
What works: Targeted, actionable alerts.
What doesn’t: “FYI” notifications that nobody reads.
Step 8: Test your workflow end-to-end
Run through your workflow as a test user—or better yet, have someone who didn’t build it try it out. Watch for:
- Steps that don’t trigger (usually missing data)
- Actions that feel robotic or off-putting
- Places where customers could get stuck with no way out
Fix the rough spots before rolling out to real customers.
Pro tip: Don’t trust “it should work.” Click through every step yourself.
Step 9: Roll out, but keep it simple
Launch your workflow to a small group first. Get feedback from both customers and your team. Tweak as needed. Don’t be afraid to pause automation if something weird happens—better to fix fast than annoy everyone.
What to keep in mind (and what to skip)
What works
- Automating predictable, repeatable steps
- Using milestones to track progress
- Having clear handoffs to real humans
What doesn’t
- Over-automating every possible scenario
- Endless nudges or reminders
- Complex branching logic nobody understands
What to ignore
- Fancy “AI” features that promise to “delight” users (nobody is delighted by more emails)
- Building for exceptions or one-off requests—handle those manually
Keep it simple and keep improving
Customer onboarding is never “done.” Start with the basics, automate the obvious, and keep an eye on where real people get stuck. The goal isn’t zero human touch—it’s to free up your team for the stuff that matters.
Don’t get caught up in hype or over-engineering. Ship something simple, learn from it, and tweak as you go. That’s how you actually get value from Endgame—and keep your onboarding from becoming a black hole.
Now, go automate the boring stuff. And don’t forget to check your own inbox for those “welcome” emails.