If you’ve ever watched a new sales rep flounder on day one, you know the pain—and the cost—of slow onboarding. Missed quotas, burned leads, and endless hand-holding. If you want your new hires to actually stick around and produce, you need a system that works. This guide is for sales managers, enablement folks, or honestly anyone stuck with the “can you just get the new reps trained up?” problem.
I’m going to walk you through using Pickleai training modules to get reps up to speed without overcomplicating things. No fluff, no empty promises—just straightforward steps, some pitfalls to dodge, and a few hard-won lessons.
Why onboarding flops (and how training modules can help)
Let’s get real: most onboarding is either a firehose of info or a slog through outdated slide decks. New reps tune out, forget half of it, and end up peppering your top sellers with basic questions for weeks.
Done right, training modules break things into manageable chunks, let reps learn at their own pace, and actually track what’s working. Pickleai’s modules are built for this—bite-sized, repeatable, and easy to update. If you’re still relying on PDFs and shadowing, you’re missing a chance to save everyone a lot of headaches.
What works: - Short, focused modules (5–15 minutes max) - Real-world scenarios and examples, not just theory - Built-in checks for understanding (quizzes, call reviews)
What doesn’t: - Marathon onboarding days - Generic “one size fits all” content - Making people memorize scripts by heart
Step 1: Map out what matters (and what to skip)
Before you touch a single tool, figure out what your reps actually need to know to survive their first two weeks. Not everything—just what’ll get them talking to prospects, booking meetings, and not embarrassing themselves.
Don’t try to cover: - The entire company’s history - Advanced negotiation tactics - Product features they won’t see for months
Focus on: - Who your target customers are (and aren’t) - How to use the CRM and book meetings - What a “good” conversation sounds like - Where to find answers when they’re stuck
Pro tip: Ask your best reps what they wish they’d known on day one. Their answers are usually more practical than anything in a training manual.
Step 2: Break content into small, logical modules
Now it’s time to turn what matters into actual training modules. With Pickleai, you can split content into short, focused lessons instead of one big block. If you’re tempted to cram too much into one module, don’t—attention spans are short, especially for new hires.
How to break it up: - Intro to your buyers: Who are they? What do they care about? - Discovery call basics: What to ask, what to listen for - CRM how-tos: Navigating, logging calls, next steps - Product crash course: Top 3 features, common objections - Common mistakes: What trips up new reps (with real examples)
Keep each module focused on a single outcome. If it takes more than 15 minutes to get through, it’s probably too much.
Step 3: Build or adapt your modules in Pickleai
Log in to Pickleai and start creating your modules. If you’ve got existing content (slides, docs, call recordings), you can upload or link it in, but don’t just dump everything in there. Pickleai’s strength is in keeping things short and interactive.
Tips for building solid modules: - Use real call snippets—not just made-up scripts - Add quick quizzes or “what would you do?” choices - Include links to cheat sheets or templates - Keep the design simple—don’t obsess over branding or colors
If you’re new to Pickleai, try using their templates. They’re not perfect, but they’ll save you a lot of time.
What to skip:
Don’t spend weeks perfecting every slide. Reps remember what they do, not what they read.
Step 4: Launch to your new reps (but don’t just dump it on them)
Once your modules are ready, roll them out to your new hires. Resist the urge to just email a login and hope for the best—walk them through what’s there, what’s expected, and how to get help.
How to set them up for success: - Give a quick walkthrough of Pickleai’s dashboard and where to start - Set clear expectations (e.g., “Finish Module 1 by Friday”) - Pair them with a “buddy” or point person for questions - Let them know it’s okay to revisit modules or ask for more detail
And please—don’t make the mistake of throwing them into live calls until they’ve passed the basics. You’ll save everyone a lot of pain.
Step 5: Track progress and actually follow up
One of the best things about Pickleai is the progress tracking. But it’s only helpful if you actually use it. Check in on who’s done what, where people are getting stuck, and use that info to coach—not to micromanage.
What to look for: - Who’s breezing through and who’s stalled out - Which modules get the most replays (usually where people are confused) - Quiz results or call scores—see where the gaps are
Pro tip: If you see several reps struggling in the same place, the problem’s probably with the training, not the reps.
Step 6: Get feedback and tweak—not just once, but regularly
No onboarding process is perfect out of the gate. Ask your new reps what made sense and what felt like filler. Update your modules as you go. The nice thing about digital training is you can fix things fast—no need to print new binders or wait for next quarter’s “training refresh.”
Good ways to get feedback: - Quick surveys after each module (“What was helpful? What was confusing?”) - 10-minute check-ins after their first week on the phones - Watching which resources get used and which get ignored
Ignore the urge to make everything “perfect” before you launch. You’ll learn more from live feedback than from endless planning.
What to ignore (unless you like wasting time)
- Overly long “culture” videos—nobody cares, especially on day one
- Fancy onboarding portals with gamification and badges (unless reps ask for it)
- Information that’s “nice to know” but not needed in week one
Your reps want to win, not watch another talking head video about “the company mission.” Give them what they need, cut the rest.
Keep it simple, iterate, and don’t overthink it
You don’t need a 60-page playbook or a three-week bootcamp to get sales reps producing. Map out what matters, break it into small steps, use Pickleai’s tools to keep it simple, and keep listening to your team. The best onboarding is the one that actually gets used—so launch, learn, and keep it moving.