If you’re wrangling a sales process that feels like herding cats—multiple steps, too many people involved, and more “Did you follow up on that?” moments than you’d like—custom workflows might be your answer. This guide is for sales managers, ops folks, or anyone tired of sticky notes and endless spreadsheets. We’ll go step-by-step through setting up custom workflows in Boomerang, a tool that’s flexible but not always intuitive. If you want real automation, less chaos, and more closed deals, keep reading.
Why Custom Workflows Matter for Complex Sales
Let’s get real: off-the-shelf sales pipeline templates rarely fit businesses with longer deal cycles or multiple touchpoints. Maybe you’re juggling approvals, legal reviews, or pilot projects before a contract gets signed. A rigid workflow won't cut it. You need something that adapts to you—not the other way around.
Boomerang’s main strength is its customization. But that also means you’ll need to make some decisions up front. If you’re hoping for “just click and it works,” prepare to do a little planning. The good news? Once your workflow’s in place, you’ll spend less time nagging and more time selling.
Step 1: Map Out Your Actual Sales Process (Don’t Skip This)
Before you touch Boomerang, write down how deals actually move through your company. Not how you wish they moved. You’ll want to know:
- What are the key stages? (e.g., Lead In, Discovery Call, Proposal Sent, Legal Review, Won/Lost)
- Who gets involved at each step? (Sales rep, manager, legal, finance, etc.)
- Where do deals usually stall or get stuck?
- What follow-ups or approvals are non-negotiable?
Pro tip: Grab a whiteboard or sketch it on paper. If your process is a mess, that’s not Boomerang’s fault. Fix it now or you’ll automate confusion.
Step 2: Get Familiar With Boomerang’s Workflow Features
Boomerang’s workflow system is powerful, but it’s not magic. Here’s what you can actually do:
- Custom stages: You can create as many as you want, with custom names.
- Conditional logic: Move deals to different stages based on outcomes.
- Automated tasks: Trigger emails, reminders, or assignments when a deal hits a certain stage.
- Role-based permissions: Limit who can see or act on specific stages.
- Integrations: Connect with email, Slack, CRM, or other tools—if you set it up.
What you can’t do: Boomerang won’t read your mind or fix a broken process. It’s also not great for super granular reporting (think: custom dashboards by default), so plan accordingly.
Step 3: Build Your Workflow Skeleton in Boomerang
Now it’s time to get your hands dirty. Here’s the basic process:
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Log in and go to Workflows.
Usually found in the main nav, sometimes under “Automation” or “Pipeline.” -
Click “Create Workflow.”
Name it something obvious, like “Enterprise Sales Process.” -
Add your stages.
Click “Add Stage” and match each one to the real-world steps you mapped out. Don’t overcomplicate—5-8 stages is plenty for most. -
Set up transitions.
For each stage, define what can happen next. Example: From “Proposal Sent,” can the deal move to “Negotiation,” “Lost,” or “Waiting for Legal?” Be explicit. -
Assign owners and permissions.
Decide who’s responsible at each stage. If legal needs to approve before moving forward, lock down the next step until they say yes. -
Save and sanity check.
Run through a fake deal to see if you can move from start to finish without getting stuck. If you’re confused, so will your team.
Don’t:
- Add every possible scenario up front. You’ll drown.
- Assign 10 people to approve every stage (unless you love bottlenecks).
Step 4: Add Automation and Reminders Where It Actually Helps
Automation is great—for stuff you do over and over. Here’s what’s worth automating in Boomerang:
- Automatic task creation: When a deal hits “Proposal Sent,” auto-create a reminder for the rep to follow up in 3 days.
- Approval requests: Automatically ping legal or finance for review at the right stage.
- Notifications: Send Slack or email alerts for key milestones or stuck deals.
- Field updates: Auto-fill “Close Date” when a deal moves to “Won.” Small, but saves clicks.
What’s not worth automating:
- Edge cases you see once a year.
- “Just in case” reminders. Too many, and people tune them out.
Pro tip: Start with one or two automations, then add more as your team asks for them. Don’t let automation become just more noise.
Step 5: Test With Real Deals (and Real People)
Here’s where most setups fall apart. Before unleashing your workflow on the whole team:
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Pick a few deals in progress.
Try moving them through the new workflow. What breaks? What’s confusing? -
Ask your team to try it.
Give them a checklist. What did they expect to happen? What did they miss? -
Watch for bottlenecks.
If deals get stuck, is it the software or your process? Fix it before rolling out wider. -
Collect honest feedback.
Not “It’s great!” but “I can’t find where to mark a deal as Lost.” That’s what you need to hear.
You’ll spot a bunch of little things—missing automations, confusing stage names, or permissions that block progress. This is normal.
Step 6: Roll Out and Train (Without the Hype)
Don’t just email the team a link and hope for the best. People hate change, especially when it messes with their commission.
- Run a short walkthrough.
Show them exactly how to use the new workflow. No fancy slides, just live clicks. - Create a one-pager.
List key stages, who does what, and where to get help. - Expect pushback.
Some folks will complain. Listen, but don’t let it derail you unless it’s a real workflow killer. - Track adoption.
Watch who’s using it and who’s not. Quietly check in with stragglers.
What to ignore:
- Requests to make the workflow fit every possible exception. The goal is consistency, not a choose-your-own-adventure.
Pro Tips and Honest Observations
- Start simple.
The more complex your workflow, the less likely anyone will use it. Complexity breeds workarounds. - Name stages clearly.
“Waiting for Approval” means nothing. “Legal Review Needed” is better. - Don’t automate everything.
If you automate every handoff, people stop thinking. Keep some manual checks where judgment matters. - Review quarterly.
Your sales process will evolve. Revisit the workflow before it gets stale. - Integrations can be hit-or-miss.
Boomerang plays nice with some tools, but not all. Don’t bank on a plug-and-play Zapier experience. - Reporting is basic.
If you need fancy analytics, export data and use a spreadsheet or BI tool.
Keep It Simple and Iterate
Custom workflows in Boomerang can be a game-changer for complex sales—but only if you keep things clear and practical. Don’t try to solve every problem at once. Start with your real process, automate the boring stuff, and let your team get used to it. Tweak as you go. The goal isn’t a “perfect” workflow—it’s one that actually gets used and closes deals.