If your sales team burns hours chasing signatures and nudging managers to approve deals, you’re not alone. Manual contract approvals are a hassle—slow, easy to mess up, and nobody likes babysitting paperwork. The good news: Docusign can take a lot of that pain off your plate, but only if you set it up the right way. This guide is for sales ops, enablement, or anyone wrangling sales contracts who wants less busywork and fewer dropped balls.
Below, I’ll walk you through each step to automate contract approvals in Docusign, point out what’s actually useful, and flag the stuff that sounds nice in theory but rarely works out in practice.
Step 1: Map Out Your Approval Workflow—Before You Touch Docusign
Before you click around in Docusign, get clear on how your contract approval actually works (or should work). Automating a broken process just makes mistakes faster.
Checklist: - Who needs to approve contracts? (Think sales managers, legal, finance, etc.) - Does the order matter? (e.g., sales manager first, then legal) - Are there different rules for different deal sizes, products, or regions? - What happens if someone’s out of the office? - What should happen if a contract is rejected?
Pro tip:
Draw this out on paper or use a whiteboard tool. Visualizing the process makes it way easier to spot gaps or people who don’t really need to be involved.
What to ignore:
Don’t try to automate every edge case right away. Start with the common paths—those cover 80% of your deals.
Step 2: Set Up Roles and Templates in Docusign
Once you know your workflow, you’ll need to create templates in Docusign. Templates save time and help your team stick to the process, instead of freelancing every deal.
How to do it: - In Docusign, go to the Templates section. - Create a new template for your standard contract. - Add “roles” for everyone in the approval chain (e.g., Sales Rep, Sales Manager, Legal Reviewer, Customer). - Assign each role to the correct signing or approval order.
Why roles matter:
Roles let you reuse the same template for every deal. You just fill in names and emails—Docusign routes things automatically.
Heads up:
If your approval path changes based on deal value (say, director approval for deals over $100k), you’ll need multiple templates or a more advanced setup using Docusign’s conditional routing (see step 4).
Step 3: Use Routing Order to Control Approvals
Docusign lets you set the order in which people receive and approve/sign the contract. This is how you prevent deals from jumping the line or getting stuck with the wrong person.
Set it up like this: 1. Sales Rep (fills in the customer info, maybe signs first) 2. Sales Manager (approves or rejects) 3. Legal (reviews, possibly signs) 4. Customer (final signer)
You choose if someone is just “approving” or actually “signing”—Docusign handles both.
What works:
Linear routing (one after another) is simple and reliable. Parallel routing (everyone at once) is faster but can create headaches if someone changes the doc after others reviewed it.
What doesn’t:
Don’t overcomplicate things with fancy routing unless you really need it. More steps = more things to break.
Step 4: Set Up Conditional Routing (If Needed)
For big teams, rules can get complicated—like only needing VP approval for huge deals, or legal review for certain contract types. Docusign’s “Conditional Routing” can handle some of this.
How it works: - In your template, set up rules based on fields (e.g., “Deal Size”). - Tell Docusign: “If Deal Size > $100,000, send to VP for approval after Sales Manager.” - Conditional logic can route deals different ways automatically.
Reality check:
Conditional routing is powerful, but the setup isn’t always obvious. Testing is key. Also, some features may require higher-tier Docusign plans (Enterprise or Business Pro). Double-check your subscription before you sink hours into setup.
Pro tip:
Document your routing rules somewhere outside Docusign, so you don’t forget what you did six months from now.
Step 5: Pre-Fill and Automate Where You Can
The fewer fields your team has to fill out, the less chance for mistakes. Docusign lets you pre-fill fields and even pull info from other systems.
Shortcuts: - Use Docusign’s “PowerForms” to let reps start contracts from a web link with some data pre-filled. - Integrate Docusign with your CRM (like Salesforce) so deal details auto-populate in the contract. - Set up field validation so required info (like customer legal name) can’t be skipped.
What’s overrated:
Don’t expect CRM integrations to work perfectly out of the box. It takes some admin elbow grease (and sometimes a consultant) to get fields matching up correctly.
Step 6: Build Simple Notifications and Reminders
Automations are pointless if people miss the emails. Docusign sends notifications by default, but you can tweak reminders and escalation.
To do: - Set up automatic reminders for signers/approvers who haven’t acted after X days. - Add escalation rules (e.g., if a manager doesn’t approve in 3 days, notify their boss). - Optionally, set up Slack or Teams notifications using Docusign integrations or via Zapier.
What works:
Simple, relentless reminders. Don’t get fancy—just make sure deals don’t get stuck in limbo.
What to skip:
Over-notifying people. If everyone gets every alert, they’ll tune them out. Target reminders to the folks who need to act.
Step 7: Train Your Sales Team (and Keep It Simple)
No automation survives first contact with a busy sales team unless it’s dead simple. If you want your process to stick:
Best practices: - Run a 30-minute live demo for the sales team showing the new workflow. - Create a one-pager or short video on “How to send a contract in Docusign.” - Show what happens if someone skips a step or rejects a contract—no surprises.
Pro tip:
Make it easy for folks to ask for help or report issues. A shared Slack channel or email alias does the trick.
What doesn’t help:
Lengthy manuals or “training portals” nobody reads. Keep it practical and just-in-time.
Step 8: Monitor, Tweak, and Improve
Once things are running, don’t just walk away. Watch for bottlenecks or confusion.
How to stay on top of it: - Check Docusign’s built-in reports to see where contracts get stuck most often. - Talk to your team—ask what’s annoying or unclear. - Refine templates and routing rules every quarter (or after big team changes).
Warning:
Don’t try to automate every possible exception. That’s how you end up with a Frankenstein process nobody understands.
Honest Takes: What Works, What Doesn’t
What actually helps: - Templates and roles: These save tons of time and reduce mistakes. - Linear, simple approval chains: Fewer moving parts = fewer headaches. - Regular feedback from the sales team: You’ll find out what’s broken fast.
Overhyped or rarely worth it: - Ultra-fancy integrations: Unless you have a full-time admin, keep it simple. - Trying to automate legal review for every contract: Sometimes a manual step is safer. - Chasing “zero clicks” for sales: Some input is unavoidable—focus on reducing, not eliminating, effort.
Keep It Simple, Iterate Often
Automating contract approvals in Docusign isn’t rocket science, but it’s easy to overthink. Start with your most common workflows, get buy-in from the sales team, and improve as you go. Most importantly, don’t let perfect be the enemy of good—every step you automate is one less thing to chase down.
If you hit a wall, simplify. Complexity is the enemy here. And remember: you’re not locking yourself in forever. Adjust as your team and deals evolve. Contract automation should make your life easier, not add another mess to clean up.