Sales teams spend more time wrangling emails and following up than actually closing deals. If you’re sick of letting leads slip through the cracks, you’ve probably looked into tools that claim to “automate your workflow” or “unlock AI-powered sales.” Most are heavy on buzzwords and light on actual results. Boomerang is different—it’s practical, easy to set up, and (if you use the right features) can actually help your team reach more prospects without burning out.
This guide is for sales managers, SDRs, and anyone looking to get their team out of email hell and into the win column. Here’s how to set up Boomerang’s AI features the right way—no fluff, no wasted time.
Step 1: Get Boomerang Set Up for Your Team
Before you can use the AI features, you need to get Boomerang up and running. It works as an add-on for Gmail and Outlook, so you don’t have to switch email providers or learn a new system.
Here’s what you need to do:
- Install Boomerang: Go to your email client’s add-on or extension store. Search for “Boomerang” and install it. Each team member will need to do this on their own account.
- Connect Accounts: Log in and grant Boomerang access to your email. This is where some folks get nervous about privacy—Boomerang has a decent track record, but always check your company’s IT policy first.
- Choose a Plan: The AI features aren’t included on Boomerang’s free plan. If you want access to things like Respondable or AI scheduling, you’ll need a paid plan. No, there’s not a secret workaround.
Pro tip: Start with a small group before rolling it out to your whole team. That way, you can spot any issues early and avoid mass confusion.
Step 2: Enable and Configure AI Features
Boomerang’s AI features aren’t all turned on by default. Here’s how to find the ones that actually help sales teams save time.
The AI Features That Matter
- Respondable: Uses AI to analyze your emails in real time and tells you how likely you are to get a response.
- Smart Calendar Scheduling: Lets you offer times for meetings and have Boomerang handle the back-and-forth, including time zone headaches.
- Follow-Up Reminders: Not strictly “AI,” but uses smart logic to remind you when you don’t get a reply—critical for sales.
How to Turn Them On
- Go to Boomerang Settings: Find the Boomerang icon in your email. Click it and head to Settings.
- Enable Respondable: There will be a toggle for Respondable. Turn it on for each user who wants AI-driven email advice.
- Set Up Smart Scheduling: Enable “Bookable Schedule” or “Suggest Times” features. You’ll need to connect your calendar (Google or Outlook).
- Adjust Reminders: Set default follow-up times for your team. (Example: 2 business days after no reply.)
What to skip: Skip the “Inbox Pause” feature for sales teams. It’s great for focus, but sales relies on fast replies. If you must use it, set exceptions for VIP leads.
Step 3: Train the Team (Without Turning It Into a Project)
Most AI tools flop because nobody uses them right. Don’t overcomplicate this—show your team the basics, then let them run with it.
Keep It Simple
- Respondable: Show how to read the Respondable score. Green is good; yellow or red means tweak your email.
- Scheduling: Demo how to insert available times or share the booking link. No need for a PowerPoint.
- Follow-Ups: Teach how to set reminders when sending emails. Takes two clicks.
Don’t: Force everyone to use every feature. Let your top sellers pick what works for them.
Pro tip: Record a 5-minute screen share walking through the top three features. Send it to the team—no need for a 1-hour training.
Step 4: Use Respondable to Write Better Sales Emails
Here’s where the AI actually helps. Respondable analyzes your email while you write and gives you suggestions to improve your chances of getting a reply. It looks at things like:
- Subject line clarity
- Length (not too long, not too short)
- Reading level (ditch the jargon)
- Question count (don’t overwhelm)
How to Use It
- Write your email as usual.
- Check the Respondable bar: It’ll show a score (0-100) with color coding.
- Make changes if needed: If your score is low, Respondable will tell you why (e.g., “Too many questions” or “Subject unclear”). Edit and re-check.
What works: Respondable is pretty good at flagging overlong or confusing emails. If you’re sending out cold pitches or follow-ups, use it.
What doesn’t: Don’t spend forever chasing a perfect score. Sometimes a “yellow” email is fine—especially if it gets to the point.
Step 5: Automate Scheduling Without the Awkwardness
Back-and-forth to find a meeting time is nobody’s idea of productivity. Boomerang’s Smart Scheduling features help you avoid this.
Two Ways to Schedule
- Suggest Times: While composing an email, click “Suggest Times.” Pick a few slots, and Boomerang inserts them as clickable options.
- Bookable Schedule: Share a link to your calendar so prospects can grab any open slot.
How It Saves Time
- Handles time zones automatically (no more “wait, is that EST or PST?”)
- Automatically removes times as they’re booked
- Sends reminders to both sides
What works: Great for demos, discovery calls, and any meeting where you want to look pro without playing calendar ping-pong.
What doesn’t: If your calendar is a mess (lots of private holds, odd events), double-check what you’re exposing before sharing your link.
Pro tip: Set boundaries. Only offer times when you’re actually available to sell. Protect your best prospecting hours.
Step 6: Set Up Automated Follow-Up Reminders
The money is in the follow-up. Boomerang’s reminders mean you don’t have to keep a sticky note or spreadsheet of who to chase.
How to Set Up
- When sending an email: Look for the “Remind me if no reply” checkbox. Set your interval (e.g., 2 days, 1 week).
- Choose trigger: You can set it for “if no reply,” “regardless,” or even “if not opened.”
- Get reminded: Boomerang brings the email back to your inbox if there’s no response.
Tips
- Be realistic. Don’t spam someone daily.
- Batch your follow-ups—set aside time each day to handle reminders.
What works: You’ll close more deals just by remembering to follow up, period.
What doesn’t: No AI can make a bad pitch work. Don’t expect reminders to save you if your offer stinks.
Step 7: Measure and Adjust (But Don’t Drown in Data)
AI tools love to promise “actionable analytics.” In practice, you only need to check two things:
- Are response rates going up? (Check Respondable’s feedback and your CRM.)
- Are you booking more meetings, faster? (Check your calendar and team logs.)
If you’re not seeing results, ask your team what’s actually helpful and what’s a waste of clicks. Kill features that don’t help, even if they look shiny.
What to Ignore
- “AI Write For Me” Tools: Boomerang doesn’t write emails for you (and that’s probably for the best). You still need to know your prospect and your pitch.
- Overly Aggressive Reminders: Don’t let Boomerang nag prospects into unsubscribing.
- Feature Bloat: Stick to the basics—Respondable, scheduling, reminders. The rest is just noise for most sales teams.
Keep It Simple and Iterate
Getting value from Boomerang’s AI features isn’t about setting up every bell and whistle. Nail the basics: write better emails, schedule faster, follow up reliably. Start with a handful of features, see what actually saves time, and tweak as you go. Most of all, don’t let the tool run your process—use it to support the way your team sells best.
You don’t need to out-automate the competition. You just need to make it easier for your team to do what they do best: connect and close.