If your job involves onboarding new enterprise clients, you already know it’s never as easy as dropping a welcome email and moving on. Enterprise deals mean higher expectations, more people involved, and way more things that can fall through the cracks. This guide is for anyone tasked with smoothing out that onboarding chaos—sales engineers, implementation managers, onboarding pros, or even founders wearing too many hats.
We’ll walk through using Airship, a workflow automation tool, to build a real onboarding process that works for enterprise clients—not just in theory, but in the messiness of real life. You’ll see what works, what’s overhyped, and how to actually get automated onboarding off the ground (without getting stuck in endless “process design” meetings).
Why Automate Enterprise Onboarding in the First Place?
Let’s be honest: onboarding by hand doesn’t scale, and copy-pasting the same checklist into a dozen docs leads to mistakes. Automation won’t fix a broken process, but it will:
- Cut down on manual busywork (think: chasing docs, tracking steps)
- Make onboarding more consistent (even if your team changes)
- Give clients a better, more predictable experience
- Surface bottlenecks early, before a VP starts asking why nothing’s live
But don’t expect automation to do all the work for you. You’ll still need to think through each step and fix your process before you automate.
Step 1: Map Out the Real Onboarding Journey
Before you touch Airship, grab a notepad (or whiteboard, or napkin). List every step your team actually takes to get a new enterprise client live—not just the “official” process, but the workarounds and side chats that happen every week.
Common steps look like:
- Kickoff call scheduled
- Legal and security docs exchanged
- Technical integration started
- Data imported/migrated
- User training delivered
- Go-live checklist signed off
Pro tip: Talk to the folks who do the work. What steps get skipped? Where do things get stuck? If you automate a broken process, you just make the pain happen faster.
Step 2: Choose What to Automate (and What to Leave Manual)
Not everything should be automated. Airship is great at moving info, nudging people, and tracking progress—but some steps need a human touch.
Automate:
- Sending reminders (e.g., “Please upload your logo”)
- Assigning tasks to the right team member
- Notifying sales/CS when a client finishes a step
- Tracking document status (signed, pending, etc.)
- Creating tickets or tasks in tools like Jira, Asana, or Slack
Leave Manual:
- Custom client training sessions
- Handling weird legal exceptions
- Relationship-building calls
If you try to automate the high-touch or unpredictable stuff, you’ll end up frustrated (or worse, miss something important).
Step 3: Build Your Client Onboarding Workflow in Airship
Now you can open up Airship and start building. Here’s how to get a basic, but actually useful, workflow off the ground.
3.1. Set Up Airship for Your Team
- Invite your teammates: Don’t just go solo. Bring in sales, CS, onboarding, and technical folks who need visibility.
- Connect your tools: Airship integrates with email, Slack, Asana, Google Drive, DocuSign, and more. Hook these up now—it’ll save you headaches later.
Heads up: Some integrations need admin permissions. Get IT buy-in early so you’re not stuck waiting.
3.2. Create a New Workflow
- Start with a template: Airship has some basic onboarding templates, but don’t expect them to fit your enterprise process out of the box. They’re a starting point, not a finished product.
- Lay out your steps: Drop in each major onboarding milestone. Name them clearly—no one wants to guess what “Phase 2: Deliverables” means.
- Assign owners: Every step should have a clear owner. “Team” won’t cut it.
3.3. Add Automation Where It Actually Helps
- Auto-assign tasks: When “Kickoff call scheduled” is done, auto-create follow-up tasks for technical setup, security review, etc.
- Trigger reminders: If a document isn’t signed in 3 days, ping the client and your legal team.
- Move files automatically: When a client uploads files, push them into the right folder in Google Drive or your doc management system.
- Sync with other tools: Automatically create Jira tickets or Asana tasks as steps progress, so nothing falls through the cracks.
What to skip: Don’t waste time automating steps you do once a year, or that always get changed on the fly. Focus on repeated pain points.
Step 4: Test with a Real Deal (Not a Dummy Account)
The first time you run your new Airship workflow, use a real, low-risk client—not a test account. Why? Because demo data never acts like real life. Watch for:
- Steps that don’t make sense or get skipped
- Tasks that end up assigned to the wrong person
- Automated messages that sound robotic or confusing
- Integration failures (these always pop up the first time)
Keep a running list of what breaks or annoys you. Don’t try to fix everything at once—just patch the biggest leaks.
Step 5: Get Your Team (and Clients) Onboard
Automation is useless if nobody uses it. Here’s how to get buy-in without endless meetings:
- Show, don’t tell: Walk the team through the workflow. Run a real client through it, live.
- Make improvements easy: Encourage people to flag steps that are pointless or confusing.
- Give clients a simple view: Airship can provide clients with a progress tracker. Don’t flood them with tasks—keep their to-do’s short and clear.
- Document exceptions: For the “one weird client” cases, have a manual override or a way to skip steps.
Don’t: Force everyone onto the workflow on day one. Start with one or two clients, collect feedback, and tweak.
Step 6: Measure, Fix, and Iterate
Automation isn’t “set and forget.” The fastest way to kill adoption is to ignore feedback or let the workflow get stale.
- Review completion rates: Are steps getting stuck? Is someone always dropping the ball?
- Collect feedback: Short, honest check-ins beat long surveys. Ask, “What’s annoying about using this?”
- Update as you go: As your process changes (new legal docs, new integration steps), keep the workflow up to date. Outdated steps will get ignored.
Pro tip: Schedule a 30-minute review every quarter. No one likes meetings, but this one keeps onboarding from quietly falling apart.
What Airship Does Well—and Where It Struggles
What works:
- Easy to build linear, checklist-style workflows (the bread and butter of onboarding)
- Good integration with common SaaS tools (email, docs, Slack, task trackers)
- Decent client-facing portals for status tracking
What’s not perfect:
- Complex branching or “choose your own adventure” onboarding gets messy fast—Airship can do it, but it’s easy to lose track.
- Reporting is basic. If you need deep analytics, you’ll need to export data.
- Notifications can get noisy if you over-automate. Less is more.
Ignore the hype:
- “No code” doesn’t mean “no thinking.” You still have to design a sane process.
- Automation won’t fix poor communication. It just makes bad news travel faster.
Keep It Simple, Review Often
Don’t get caught up building a “perfect” onboarding process. Start with the steps that cause the most pain, automate those, and roll out improvements as you go. Airship (or any tool) is just that—a tool. The real magic comes from clear steps, real ownership, and a willingness to fix what doesn’t work.
Build, test, tweak, repeat. That’s how you turn onboarding from a fire drill into something your team—and your clients—can actually count on.