If you’re tired of deals falling through the cracks or your sales team winging it, you’re not alone. Deal pipelines are supposed to bring order to the chaos, but too often they end up as yet another thing to maintain. This guide is for anyone who wants to actually use Overloop pipelines to get deals moving, not just tick a box for management.
Below, I’ll walk you through how to set up and customize pipelines in Overloop, what to focus on, and what to skip. No fluff, no jargon — just what you need to get started and keep it workable.
Why Deal Pipelines Matter (But Only If You Keep Them Practical)
A deal pipeline is just a fancy way of saying, “Here’s where every deal stands, and what needs to happen next.” The point isn’t to have a pretty dashboard; it’s to help you spot bottlenecks, prioritize work, and make sure nothing gets forgotten.
But here’s the thing: overcomplicated pipelines are worse than none at all. If you’re spending more time updating the pipeline than actually selling, you’ve missed the point. The goal is clarity, not bureaucracy.
Step 1: Map Out Your Real-World Sales Process
Before you even log in, grab a notepad (or open a doc) and sketch out your sales process as it actually happens. Not how you wish it worked — how it works on a Tuesday afternoon when things are messy.
- List each major stage a deal goes through, from first contact to closing (and maybe even onboarding).
- Don’t get cute with stage names. If you call it “Demo Scheduled,” call it that.
- Ask your team for input — they’re the ones using this every day.
Pro tip: Fewer stages are better. Five to seven is usually enough for most B2B sales cycles. More than that, and you’ll spend your life dragging cards around.
Step 2: Set Up a New Pipeline in Overloop
Once you know what your process really looks like, it’s time to put it into Overloop.
- Login to Overloop and head to the “Pipelines” section under the Deals menu.
- Click “Create new pipeline.”
- Give your pipeline a clear name. If you run more than one line of business (say, SMB and Enterprise), make a separate pipeline for each.
- Add your stages, one by one, in the order they actually happen. Use the names from your draft — keep it familiar.
- Hit save.
Overloop lets you create multiple pipelines, but don’t go overboard. Start with what you need right now.
Step 3: Customize Pipeline Stages (But Don’t Overthink It)
Customizing stages is where people get stuck. Here’s what actually matters:
- Names should match real actions — “Proposal Sent,” not “Phase 2.”
- Descriptions help newbies — Overloop lets you add notes or tips to each stage. Briefly explain what “done” looks like in that stage.
- Order matters — Drag and drop to rearrange. If deals often skip a step, maybe you don’t need that stage at all.
What to ignore: Don’t add “fun” or “aspirational” stages like “Relationship Building” if you can’t define when a deal enters or leaves that stage. If it’s fuzzy, it’s useless.
Step 4: Set Up Stage-Specific Actions and Reminders
Pipelines are only useful if they help you do something. Overloop lets you:
- Assign tasks or reminders to each stage. For example, auto-create a follow-up task when a deal enters “Negotiation.”
- Set probability percentages. This helps with forecasting, but don’t obsess over it. Use rough numbers (10%, 50%, 90%) and move on.
- Automate emails or notifications. If you have a stage where every deal gets the same email, set up an automation. But don’t go nuts — nobody likes spammy “checking in” emails.
Pro tip: Start simple. You can always add more automation later, but cleaning up bad automations is a pain.
Step 5: Add Custom Fields That Actually Help
Overloop lets you add custom fields to deals. This is handy, but easy to abuse.
- Only add fields you’ll use for filtering or reporting. If you never filter by “Industry,” don’t add it.
- Keep required fields to a minimum. Otherwise, people will make stuff up just to move a deal forward.
- Review fields quarterly. Delete what’s not being used.
What to skip: Don’t build a CRM form that looks like a tax return. You only need a few fields to run a clean pipeline.
Step 6: Move Existing Deals Into the Pipeline
If you’re switching from spreadsheets or a different system, you’ll need to migrate your deals:
- Use Overloop’s import tools (CSV is usually easiest).
- Map your old stages to your new ones. Some deals might not fit perfectly — that’s normal.
- Once imported, do a quick audit. Make sure nothing’s missing or in the wrong stage.
Don’t worry about getting it perfect the first time. Clean up as you go. It’s better to have an 80% accurate pipeline you use than a 100% accurate one you never look at.
Step 7: Train Your Team — And Make Updates Routine
Even the best pipeline is useless if nobody uses it. Here’s what actually works:
- Show, don’t just tell. Walk through a real deal, moving it step-by-step.
- Set a regular time to review the pipeline. Weekly works for most teams.
- Make it safe to suggest changes. If a stage isn’t working, fix it. Don’t let the pipeline become gospel.
You want the pipeline to be a living tool, not a dead document.
What Works Well in Overloop (And What to Watch Out For)
The Good: - The drag-and-drop UI is straightforward. No learning curve. - You can set up multiple pipelines if you actually need them. - Automations save time on repetitive stuff, if used sparingly.
The So-So: - Reporting is fine, but not amazing. Don’t expect magic insights. - Too many custom fields or stages can slow things down. Resist the urge to over-customize.
The Watch-Outs: - If you don’t keep the pipeline up to date, it quickly becomes useless. - Automations can get out of control if you’re not careful. - If the process changes, make sure the pipeline changes too. Otherwise, people will just stop using it.
Tips for Keeping Your Pipeline Useful
- Review regularly: Set a calendar reminder to review the pipeline every month.
- Prune ruthlessly: Delete unused stages, automations, and fields.
- Keep it visible: Make the pipeline part of your team meetings — not just something to check at quarter-end.
- Ask for feedback: Your team will spot pain points before you do.
Wrapping Up: Keep It Simple, Iterate Often
A deal pipeline in Overloop is only as good as the habits around it. Start simple, focus on what actually moves deals forward, and don’t be afraid to change things up as you learn. The best workflow is the one you’ll actually use — not the most detailed one you can dream up.
Remember: it’s better to have a basic pipeline you update every day than a “perfect” one nobody touches. Start small, tweak as you go, and let the tool serve you — not the other way around.