Using Boomerang to track prospect engagement and optimize your GTM strategy

So, you’re running a go-to-market (GTM) motion—maybe you’re in sales, biz dev, or just trying to get an actual reply from your prospects. You’ve probably heard a hundred times that “engagement is everything.” But what does that even mean, and how do you measure it without drowning in dashboards or adding another clunky tool to your stack?

If you haven’t tried Boomerang yet, it’s a simple add-on for Gmail and Outlook that tracks when (and if) people open your emails, click your links, and more. It doesn’t promise AI-powered magic, but it does give you hard data on whether your prospects are paying attention—or ghosting you.

This guide is for anyone who wants real visibility into prospect engagement, without getting lost in the weeds. I’ll walk you through how to actually use Boomerang to track what matters, spot patterns, and make changes that improve your GTM results. No fluff, no “transformative journeys”—just real steps, pitfalls, and a few shortcuts.

Why Bother Tracking Prospect Engagement?

Let’s be blunt: most prospects ignore most emails. If you’re still relying on your “sent” folder or just waiting for replies, you’re missing out on a ton of useful signals. Here’s what tracking engagement actually gets you:

  • Immediate feedback: Know if your message even made it past their inbox.
  • Timing clues: See when prospects are active (or not).
  • Follow-up ammo: No more guessing if you’re being ghosted or just lost in the shuffle.
  • Data for tweaking: Stop flying blind—use actual results to improve.

But let’s be clear: tracking won’t magically make people care about your pitch. It just gives you more honest info about what’s working, what’s not, and who’s worth your time.

Step 1: Setting Up Boomerang for Engagement Tracking

You don’t need a PhD to get started with Boomerang. Here’s what you actually need to do:

  1. Install Boomerang:
  2. Head to boomerang.html and install the plugin for Gmail or Outlook.

  3. It’s lightweight and doesn’t require IT to get involved.

  4. Enable Read Receipts and Click Tracking:

  5. When composing an email, check the “Request Read Receipt” and “Track Clicks” options.

  6. Be selective. Don’t enable tracking on every email—people notice, and it can backfire if overused.

  7. Set Up Reminders:

  8. Boomerang’s “Remind Me If No Reply” feature is underrated. Instead of letting threads die, set reminders to follow up automatically when there’s no engagement.

Pro Tip:
Boomerang’s reminders can be a lifesaver, but don’t overdo it. If you’re sending follow-ups every two days, you’ll look desperate.

Step 2: Sending Emails That Are Worth Tracking

No tool can polish a bad email. Before you start tracking, make sure you’re sending something worth opening:

  • Write like a human: Ditch the templates and jargon. If you wouldn’t reply to your own email, neither will they.
  • Keep it short: The more you write, the less they’ll read.
  • Have a clear ask: Don’t just “check in.” Give them a reason to respond.

Boomerang will show you who’s opening your emails, but if your message is weak, the data won’t help. Garbage in, garbage out.

Step 3: Interpreting Engagement Data (Without Overthinking It)

Here’s what Boomerang tells you, and how to actually use it:

  • Opened, No Clicks: They saw your message, but didn’t bite. Rethink your call to action or subject line.
  • Opened, Clicked: This is your best signal. They’re interested. Move quickly—strike while the iron is hot.
  • No Opens: Either your email went to spam, you’ve got the wrong address, or your subject line didn’t cut it.

Don’t obsess over every open. Look for patterns instead:

  • Are certain subject lines getting more attention?
  • Do some prospects only open at certain times of day?
  • Is there a drop-off after your first email?

What Not to Do:
Don’t read too much into a single open. Some people open emails out of habit, or by accident. You want trends, not anecdotes.

Step 4: Using Engagement Data to Guide Your GTM Strategy

This is where tracking pays off. Use Boomerang’s data to actually change your approach:

  • Prioritize Hot Prospects:
    If someone opens and clicks, bump them to the top of your call list. Don’t waste cycles on the coldest leads.
  • Optimize Send Times:
    Notice a prospect opens every email at 8am? Schedule your next message for then.
  • Test and Double Down:
    Try different subject lines, CTAs, or even send times. Use Boomerang’s data to see what sticks.
  • Cut the Dead Weight:
    If someone hasn’t opened three emails in a row, move on. Your time is limited.

Pro Tip:
Export your engagement data and look for patterns across your whole list. Sometimes, the biggest wins come from small tweaks (like changing a subject line or sending earlier in the week).

Step 5: Avoiding the Common Pitfalls

Boomerang is helpful, but it has limits. Here’s what to watch out for:

  • Tracking Isn’t Perfect:
    Some email clients block tracking pixels or click tracking. Don’t treat “no open” as gospel.
  • Respect Privacy:
    Overusing tracking can feel creepy. Use it for cold outreach and follow-ups, not every internal memo.
  • Don’t Automate Everything:
    The more your emails look automated, the less people trust them. Personalization still matters.
  • Don’t Chase Ghosts:
    If someone ignores you after several attempts, let it go. Engagement data tells you where to focus, not who to pester.

Step 6: What to Ignore (Seriously)

There are a lot of “advanced” features and sales hacks floating around. Here’s what you can safely skip:

  • Obsessing Over Click Maps
    You’re not running a marketing campaign. You just need to know if they clicked, not where.
  • Over-customizing Every Email
    A little personalization goes a long way, but don’t let “perfect” be the enemy of “done.”
  • Fancy Integrations
    Boomerang works best as a simple layer on top of your inbox. You don’t need a Zapier workflow for every open.

Wrapping Up: Keep It Simple, Iterate

Boomerang won't close deals for you, but it will show you who's paying attention. Use it to track engagement, spot trends, and adjust your approach. Don’t get lost in the data—pick a couple things to test, double down on what works, and move on from what doesn’t.

The best GTM strategies aren’t complicated—they’re just consistent, honest, and built on real feedback. Use Boomerang as a tool, not a crutch, and keep tweaking as you go. The results will follow.