So you want to automate your outbound sales emails, but you don’t want to blow a ton of cash or wrangle another complicated tool. If you’re using Gmail, Boomerang is one of the simplest ways to run basic email sequences without getting sucked into another bloated sales platform. It’s not magic, but if you set it up right, it saves hours of copy-pasting, scheduling, and following up.
This guide is for sales reps, founders, or anyone hustling to get more replies from outbound emails—without turning their inbox into a time sink. Let’s get into the real details: what Boomerang can (and can’t) do, and exactly how to set up your own killer outbound sequence.
What Boomerang Does (and Doesn’t) Automate
Before you spend hours tinkering, let’s be up-front:
What Boomerang can do: - Schedule emails to send later - Set follow-up reminders if nobody replies - Send recurring emails to the same person - Pause your inbox to avoid distractions
What it can’t do (at least natively): - Run true multi-step, branching sequences like Outreach or Salesloft - Personalize at scale with dynamic fields (“Hi {FirstName}”) - Track opens and clicks beyond the basics - Handle large-scale mail merges (unless you use Boomerang’s Mail Merge add-on, which is paid and limited)
In short, Boomerang is perfect if you’re sending semi-personalized, low-to-medium volume outbound emails and want dead-simple automation. If you want full-blown sales cadences, you’ll outgrow it fast.
Step 1: Prep Your Email List and Templates
Don’t wing it. A little upfront work makes automation actually pay off.
Build a clean list: - Start with a spreadsheet. Include columns for name, email, company, and any detail you want to mention. - Double-check for typos. Bad emails bounce, and too many bounces can hurt your deliverability.
Write your sequence: - Draft your initial outreach email. Keep it short, specific, and easy to reply to. - Write at least one (ideally two) follow-up emails. Seriously—most replies come from the second or third touch. - Save these as Gmail templates (use Gmail’s built-in Templates feature, under Settings > Advanced).
Pro tip: Don’t overthink personalization. Mentioning the company name and one relevant detail is usually enough. If you’re sending hundreds a day, you need more automation than Boomerang.
Step 2: Install Boomerang and (Optional) Mail Merge
If you don’t already have Boomerang, install it from their Chrome Web Store or Boomerang’s website. There’s a free tier, but you’ll probably hit the limits fast if you’re doing sales.
Mail Merge add-on:
For sending the same email to a list (with some personalization), Boomerang’s Mail Merge feature is clutch. It’s not as slick as Mailshake or GMass, but it gets the job done for basic stuff.
- Install the Boomerang Mail Merge add-on if you want to send bulk emails.
- You can upload a CSV with your contacts and use variables like {{FirstName}} in your emails.
- Warning: Gmail has daily sending limits (usually 500 for regular accounts, 2,000 for Google Workspace). Don’t burn your sender reputation.
If you’re just sending to a handful of people:
Skip Mail Merge and do it by hand with Gmail templates and scheduled send.
Step 3: Set Up Your First Outbound Email
- Open Gmail and hit “Compose.”
- Write (or paste) your first outreach email. Use a template to save time.
- If you’re using Mail Merge:
- Click the Boomerang icon, select “Mail Merge.”
- Upload your CSV, map columns to variables.
- Preview your emails—make sure personalization works.
- Set the time and date for sending.
Pick business hours in your recipient’s time zone—don’t blast people at 2am.
Pro tip: Avoid sending huge batches at once. Gmail hates spammy behavior. Space them out or use Boomerang’s “spread out delivery” option.
Step 4: Automate Your Follow-Ups
This is where Boomerang’s “Respondable” and “Remind Me If No Reply” features shine. You won’t get a fancy sequence builder, but you can chain reminders to automate the next steps.
Here’s how to do it:
- After you’ve finished writing your first email, click the Boomerang icon at the bottom of the compose window.
- Choose “Remind me if…” and select “No reply.”
- Pick your follow-up timing—common choices are 2 or 3 business days.
- Hit “Send.”
If the person replies, reminder is canceled. If not, you’ll get a reminder. - When you get reminded, send your follow-up email using your saved template.
(If using Mail Merge, you can pre-schedule follow-ups as separate bulk sends, but it’s clunky—see below.)
If you want fully automated follow-ups:
Boomerang isn’t built for multi-step sequences where follow-ups send automatically only if there’s no reply. You’ll need to send each follow-up manually when reminded, or pre-schedule using Mail Merge (but that will send regardless of whether they replied—danger if someone already responded).
Real talk:
This manual piece is the biggest limitation. If you want hands-off, rules-based automation, Boomerang isn’t your tool. But if you care about quality and reply rates, adding a personal touch to each follow-up is usually worth the effort.
Step 5: Track Replies and Stay Organized
Outbound gets messy fast. Here’s how to keep your sanity:
- Use Gmail labels. Create labels like “Outbound – 1st,” “Outbound – 2nd,” and move conversations as you go.
- Pause your inbox. Boomerang can pause incoming mail while you batch your outreach. Handy if you get sidetracked easily.
- Set calendar blocks. Reserve 30 minutes a day just to handle follow-ups and new outbound—don’t let it pile up.
Pro tip:
If someone asks to be removed or unsubscribed, do it. Don’t risk getting flagged for spam. Keep a simple “do not contact” sheet and check it before each send.
Step 6: Analyze What’s Working—And What Isn’t
Boomerang gives basic read receipts, but it’s nowhere near the analytics of full-on sales platforms. Focus on the metrics that matter:
- Reply rate: How many people are actually writing back? If it’s under 5%, your emails need work.
- Positive replies: Are you getting meetings, or just “not interested”?
- Time spent: Are you spending more time managing tools than actually selling? If yes, simplify.
What not to bother with: - Don’t obsess over open rates—lots of false positives thanks to privacy features. - Don’t chase fancy dashboards. If you want deep analytics, you’ll need something more robust (and expensive).
What Boomerang Does Well (And Where It Falls Short)
Works well for: - Small teams or solo founders who want to automate a few touches without learning a new platform - Testing messaging before investing in a bigger tool - Staying on top of follow-ups in Gmail, without CRM bloat
Falls short for: - Scaling to hundreds or thousands of prospects per week - Multi-step, rules-based sequences with branching - Advanced analytics and reporting
If you need those, look at tools like Outreach, Apollo, or Mailshake. They cost more, but save headaches at scale.
Final Thoughts: Keep It Simple and Iterate
Automating outbound with Boomerang isn’t the flashiest solution, but it beats getting buried in spreadsheets and sticky notes. Start small, focus on writing clear emails, and use automation to handle the boring parts—not to hide behind bulk sending.
Don’t overcomplicate it. Get your first sequence out, see who replies, tweak your message, and only add more automation when the process starts to feel like a chore. The best salespeople iterate fast and talk to real humans—not just send more email.
Now, go hit “Send”—and actually follow up. That’s where the magic happens.