Bringing a new sales rep onto your team is always a bit of a juggling act. There’s the usual mix of excitement, impatience, and pressure to get them ramped up fast—without tripping over every avoidable mistake. If your team’s using Dealpad to manage deals and collaborate, good onboarding is the difference between reps flying solo (bad) and actually getting value from the tool (good).
This guide is for sales leaders, managers, and enablement folks who want to get new hires set up with Dealpad workspaces—without wasting anyone’s time on fluff, or getting bogged down in endless “best practice” slides.
1. Don’t Just Dump Them In—Set Up Their Environment First
Most onboarding fails right out of the gate because nobody bothered to prep. If you want a new rep to actually use Dealpad, you need to make sure their workspace isn’t a wasteland of empty templates or, worse, a graveyard of old deals with no context.
What to do:
- Create or assign the right workspace: Don’t just add them to the “default” workspace. Make sure they’re in the teams, territories, or verticals that match their role.
- Clean up clutter: Archive out-of-date deals. Delete test data. No rookie wants to guess which pipeline is real.
- Load up relevant resources: Add recent win stories, playbooks, customer references, and current collateral—stuff they’ll actually need.
- Set permissions thoughtfully: Not everyone needs admin rights. Give them what they need to get started, and open up more as they prove they can handle it.
What to ignore:
Don’t waste time over-customizing dashboards or stuffing the workspace with “optional” widgets. The goal is clarity, not overwhelming them.
2. Walk Them Through the Real Workflow (Not Just Features)
Nobody remembers a click-by-click tour—especially if it’s just “here’s where that button is.” What sticks is seeing how Dealpad fits into the actual sales motion.
How to do it:
- Show the typical deal cycle: Walk through how your team moves a deal from lead to closed-won using Dealpad. Use a real (sanitized) example if you can.
- Highlight where reps add value: Point out when they’ll need to update deal stages, add notes, or loop in others.
- Explain the “why” for each step: Don’t just say “update the mutual action plan”—show how it helps avoid last-minute surprises.
- Call out common mistakes: For example, forgetting to tag stakeholders or not updating the next step.
Pro tip:
Record one of these walkthroughs and save it to your resource library. New hires can revisit it instead of asking the same questions later.
3. Assign Simple, Hands-On Tasks (Skip the Theory)
You can throw as many PDFs and videos at a new hire as you want—but until they actually use Dealpad to work a live deal, none of it really sticks.
What works:
- Start with a sandbox deal: Let them practice creating a deal, adding contacts, and moving through stages without risk.
- Assign real tasks: “Add your first real prospect.” “Update a mutual action plan.” “Share a workspace with a customer.”
- Give direct feedback: Don’t just say “good job.” Point out what they did right and what could be better. Be specific, not vague.
What doesn’t:
Don’t make them fill out a worksheet about “what they learned.” You want them navigating real sales scenarios, not memorizing a glossary.
4. Make “Ask for Help” the Norm, Not the Exception
Even the smartest new rep will get stuck. The best teams don’t pretend that onboarding is a one-and-done event—they build in ways to get help fast.
How to set this up:
- Pick a go-to person: Assign a buddy or mentor for the first month. Someone who actually uses Dealpad daily, not just the loudest person on Slack.
- Create a “dumb questions” channel: Make it clear that it’s fine to ask anything, and that nobody will get roasted for not knowing how to tag a stakeholder.
- Document the basics: Keep a short, living FAQ for common Dealpad questions. Link it everywhere. Update it when new stuff comes up.
Skip this:
Don’t rely on the generic vendor help center as your only resource. They’re fine as a backup, but your team will have its own quirks and best practices.
5. Integrate Dealpad Into Your Sales Routines (Or It Gets Ignored)
You can have the best onboarding in the world, but if Dealpad isn’t part of how your team actually works, new reps will drop it the second they can.
How to make it stick:
- Run pipeline reviews out of Dealpad: Make it the default, not an afterthought. If you keep using spreadsheets, so will your team.
- Make updates visible: Use Dealpad’s notifications or activity feeds in your standups or sales meetings.
- Reward good usage: When someone closes a deal and kept everything updated in Dealpad, call it out. Not with empty praise—just a quick “This is what good looks like.”
What to ignore:
Don’t force people to use every single feature. Focus on the 2-3 workflows that matter most (e.g. updating deal stages, mutual action plans, sharing workspaces with buyers).
6. Keep It Tight—Review and Adjust Onboarding Regularly
No onboarding is perfect the first time through. If you’re not tweaking your approach every few hires, you’re probably missing something.
How to keep improving:
- Ask new reps for feedback: After their first month, ask what made sense and what was confusing—then actually act on it.
- Watch for drop-off: Are new reps updating deals? Sharing workspaces with buyers? If usage drops, find out why (and fix it).
- Iterate on resources: Update walkthrough videos, FAQs, and templates when you notice patterns of confusion.
Don’t bother:
Endless surveys and “onboarding satisfaction” scores rarely tell you what you need. Focus on whether your reps are actually using Dealpad to drive deals.
Pro Tips, Honest Truths, and What to Watch Out For
- Don’t overcomplicate it. The goal is to help new reps sell, not turn them into Dealpad power users overnight.
- Focus on real deals, not test data. People care when it feels relevant to their targets and commissions.
- Watch out for “shadow systems.” If reps are still tracking deals in spreadsheets, your onboarding hasn’t landed.
- Treat onboarding as ongoing. The first week is just the start—a good process keeps supporting reps as they grow.
If you remember one thing: keep it simple, focused, and real. Fancy onboarding plans are tempting, but they rarely survive contact with actual salespeople and live deals. Set up a clean workspace, show how the tool fits real workflows, and build in regular check-ins. Iterate as you go, and you’ll have new reps up and running in Dealpad—without the headaches or the hype.