Bringing on new sales reps is always a gamble. Done right, they’re closing deals and paying for themselves in months. Done wrong, they’re frustrated, floundering, and eating up everyone’s time. If you’re reading this, you probably want to get new hires productive fast—without burning out your managers or dumping reps in the deep end.
This guide is for sales leaders, enablement folks, and even hands-on managers who want to use Outreach’s training tools to make onboarding smoother, faster, and less painful for everyone. No fluff—just real steps, honest warnings, and a few shortcuts that actually work.
Step 1: Get Your Basics in Order Before You Add Tech
Let’s be honest: Outreach is powerful, but it can’t fix a broken onboarding process. If your training is scattered, your messaging is out of date, or no one’s sure who does what—stop here and get your house in order.
Before using Outreach for training, make sure you have: - Clear job expectations and ramp-up goals - A simple, up-to-date sales playbook - Someone accountable for onboarding (not “everyone”) - Access to Outreach and the right user permissions for new reps
If you’re missing any of these, Outreach won’t save you. Fix these first. Seriously.
Step 2: Map Out a Realistic Onboarding Timeline
Don’t wing it. New reps need to know what’s expected week by week—not just a vague “shadow someone for a while.” Outreach can automate a lot, but it can’t replace a plan.
What works: - A clear 30/60/90-day plan with milestones (calls made, meetings booked, demos run) - A checklist of Outreach-focused tasks (sending a sequence, logging a call, using analytics) - Regular check-ins—scheduled on the calendar, not “when there’s time”
What doesn’t: - Dumping reps into Outreach on day one and hoping they figure it out - Pretending everyone learns at the same speed; some will need more time with the tools
Step 3: Build Training Sequences Inside Outreach
Here’s where Outreach ([outreach.html]) can actually save you time. You can build onboarding “sequences” just like you would for prospects, but for reps. Think drip campaign, but for training.
How to do it: 1. Create a dedicated onboarding sequence in Outreach for new reps. 2. Break onboarding into bite-sized steps—short videos, articles, or tasks, not hour-long marathons. 3. Schedule each piece to go out on specific days (e.g., Day 1: “How to send your first sequence”; Day 3: “Logging calls the right way”). 4. Include links to your playbook, example emails, or internal wikis. 5. Assign practical tasks—“Send yourself a test sequence,” “Book a mock meeting with your manager.”
Pro tip:
Don’t just use Outreach sequences to dump information. Mix in real, platform-based actions so reps are clicking buttons, not just reading about them.
Step 4: Use Outreach’s Analytics to Track Progress (but Don’t Overdo It)
You can see who’s completed training steps, who’s actively using Outreach, and who’s stuck. Use these numbers, but don’t micromanage—some folks need a nudge, not a daily scorecard.
What works: - Weekly reviews of activity data: Are they sending emails, making calls, logging activity? - Spot-checking quality: Are sequences personalized, or is it spray-and-pray? - Following up with reps who aren’t engaging—privately, not in a public shaming session
What doesn’t:
- Using analytics as a blunt instrument. If someone’s falling behind, ask why before assuming they’re slacking.
- Treating Outreach usage as the only measure of onboarding success. Selling is more than clicking buttons.
Step 5: Bake Practice and Feedback into the Process
Outreach makes it easy to automate, but new reps need feedback from real people. Combine digital training with human coaching—don’t pick one or the other.
How to make it work: - Have reps record mock calls or demo videos in Outreach (or your favorite screen recorder). - Review these recordings and give specific, honest feedback. “Try this opening line instead,” not just “Good job.” - Pair new hires with a “buddy” for the first month—someone who’s good at Outreach, not just the friendliest person on the team. - Hold short, regular Q&A sessions. Don’t wait until the end of the month to find out someone’s lost.
Skip this:
- Endless group training Zooms. People tune out after 20 minutes. Keep it short, or make it optional.
Step 6: Update and Improve Your Training—Don’t Set and Forget
Your sales process changes. Outreach gets new features. If your onboarding is stuck in last year’s playbook, you’re setting everyone up to fail.
Stay on top by: - Reviewing onboarding outcomes every quarter. Are new reps hitting targets? Where are they getting stuck? - Asking new hires what confused them—then fixing it for the next round. - Updating your Outreach training sequences with new tips, screenshots, or process changes.
What’s a waste of time?
- Overcomplicating things with fancy videos or a million micro-lessons. Focus on what reps actually need to do in Outreach to sell, not every obscure feature.
Step 7: Know When to Ignore the Fancy Stuff
Outreach has a ton of bells and whistles. Most new reps don’t need advanced analytics or complex sequence branching on day one.
Cut the noise: - Start with basics: sending sequences, logging calls, handling replies, and checking simple reports. - Save advanced Outreach features (A/B testing, custom triggers, deep integrations) for later. - Don’t let “learning the tool” become more important than “learning to sell.”
Remember:
If a new rep can’t send a decent email or follow up on a lead, no amount of tool mastery will save them.
Final Thoughts: Keep It Simple, Review Often
Onboarding with Outreach can be fast and effective, but only if you focus on the essentials. Set clear expectations, break training into small steps, use Outreach to automate the repeatable stuff, and always mix in real feedback. Don’t chase every new feature—get the basics right, then improve as you go.
Build your onboarding like you build your sales process: simple, clear, and always up for improvement. Don’t wait for perfect—ship it, test it, and tweak it as you learn. That’s how you get new reps selling faster, with less drama.