Onboarding new sales reps is never as simple as handing them a script and pointing to the CRM. Most reps spend their first few weeks lost in a tangle of tools, tribal knowledge, and “just ask Sarah” moments. If you’re sick of babysitting every new hire and you want a system that actually works—without turning into a micromanager—this guide is for you. We’ll walk through how to use Twain task automation to onboard sales reps so they can hit the ground running (and you can get back to your job).
Step 1: Map Out What Actually Matters
Before you automate anything, get brutally honest: What do new reps really need to succeed in their first month? Fancy “learning journeys” and endless videos sound good, but most salespeople want to know:
- Who do I talk to?
- What do I say?
- How do I log stuff so I don’t get yelled at?
Pro tip: Do this step with your last two hires. Ask them what tripped them up. You’ll find out quickly what’s fluff and what’s essential.
Must-Haves (Don’t Skip These)
- Product walkthroughs (the real features, not just the sizzle)
- How to use the CRM (for real, not the 2-hour snoozefest)
- Call scripts or talk tracks
- Lead lists and how they’re updated
- Key company policies (just the ones that’ll actually get them in trouble)
- Who to ask for help (and when)
Nice-to-Haves (But Don’t Let These Bog You Down)
- Deep-dive competitor analysis
- “Brand story” slide decks
- Inspirational videos from the CEO
Cut the noise. Focus on the actions and info that move a rep from “new” to “getting meetings booked.”
Step 2: Break the Onboarding Into Repeatable Tasks
Automation only helps if you know what you’re automating. Take your must-haves and turn them into a checklist. Seriously—write them down as individual tasks:
- Watch 5-min product demo
- Set up email signature
- Add 3 test contacts to CRM
- Shadow 2 sales calls
- Complete security training module
Keep tasks small and clear. “Get familiar with our CRM” is useless. “Log a fake opportunity” is actionable.
What works: Clear, bite-sized tasks.
What doesn’t: Vague goals or tasks that require a manager to explain every step.
Step 3: Set Up Twain Task Automation
Now, bring in Twain. If you’re new to it, Twain is a tool that helps you automate repetitive onboarding and training tasks, so new hires always know what’s next—and you don’t have to chase them.
Start With a Template
Twain lets you build task templates for new sales hires. Use your checklist from Step 2. You can:
- Set up tasks with deadlines (e.g., “Shadow sales call by Day 3”)
- Add links to resources (demo videos, CRM login, scripts)
- Assign tasks that trigger only after a previous one is complete (no more “wait, what do I do now?”)
Don’t overthink the order. If it’s not life-or-death, give reps the freedom to do things out of order. Some folks learn faster by watching than reading. Twain supports branching—use it.
Example Twain Onboarding Flow
- Intro & Welcome
- Watch welcome video (optional, but nice)
-
Read “First week at a glance” doc
-
Product Basics
- Watch product demo (link included)
-
Take product quiz (optional)
-
System Setup
- Set up email, calendar, CRM login
-
Add test lead to CRM
-
Sales Process
- Review call scripts
-
Shadow two live calls (links to calendar)
-
Compliance
- Complete security video
-
Sign code of conduct
-
First Outreach
- Send intro email to test contact
- Log activity in CRM
You can set up all of this in Twain with a mix of deadlines, reminders, and links. It’s not flashy, but it works.
Step 4: Assign and Track Progress (Without Micro-Managing)
Once your flow’s set up in Twain, assign it to each new rep as soon as they start. Twain will nudge them if they fall behind, so you don’t have to.
What You Actually Need to Track
- Are they stuck on a step for more than a day or two?
- Are they skipping steps?
- Do they keep asking the same questions (which means your instructions are unclear)?
Twain’s dashboard shows task completion and flags overdue items. Use this info for quick check-ins—no need for daily “how’s onboarding going?” messages.
Warning: Don’t use automation as an excuse to disappear. The best onboarding automates the boring stuff so you have more time for real coaching.
Step 5: Build in Feedback Loops—Keep Improving
No onboarding process is perfect out of the gate. After each hire, grab 10 minutes to ask what worked and what sucked. Use Twain to add a “feedback” task at the end:
- “What was confusing?”
- “What did you wish you had sooner?”
- “Which task felt like busywork?”
Update your Twain flow every month or two. If everyone gets stuck on a particular step, rewrite the instructions or add a quick video. If nobody uses the “CEO welcome” video, cut it.
Pro tip: Keep a running log of “questions new reps ask.” If you see the same question three times, add it to the onboarding tasks.
Step 6: Know Where Automation Falls Short
Twain will save you a ton of time, but it won’t fix broken processes or train people how to sell. Use it to:
- Get the basics out of the way without hand-holding
- Make sure nothing critical gets missed
- Give new reps a sense of progress
But don’t expect it to:
- Replace real coaching or shadowing
- Teach “gut feel” for your customers
- Make bad hires into good ones
If your onboarding feels like “check these boxes and you’ll be great,” you’re missing the point. Automation is about freeing you up for the human parts, not erasing them.
Step 7: Ignore the Hype—Keep It Simple
It’s easy to get sucked into the promise of “fully automated onboarding.” Here’s the truth: Simple wins. Fancy automations just give you more things to break.
- Stick to essential tasks.
- Review and prune your onboarding checklist quarterly.
- Use Twain to handle the stuff you don’t want to repeat over and over.
Don’t spend more time building your onboarding system than your reps spend using it.
Wrapping Up: Start Lean, Fix as You Go
If you take nothing else from this: Document the real steps, automate the basics with Twain, and keep tuning based on real feedback. Don’t worry about perfection. The best onboarding is the one you actually maintain.
Set it up once, watch where people get stuck, and tweak. You’ll save hours, avoid chaos, and (maybe) finally stop answering the same questions every Monday.
Get started, keep it simple, and let Twain do the boring stuff—so you can focus on helping real people sell.