If you’re in sales, recruiting, or any role where following up actually matters, you’ve probably wished your email tool could do more of the grunt work. Yesware is one of those tools that promises to handle follow-up emails for you, with personalization and scheduling baked in.
But if you’ve ever poked around Yesware, you’ll know: it’s easy to get lost in the mix of templates, campaigns, and tracking options. This isn’t a magic button. If you want real results—and not just “blasting” people—you’ll want to use it right. This guide breaks down, step by step, how to schedule genuinely personalized follow-up emails in Yesware, avoid the spammy pitfalls, and actually get replies.
Who This Guide Is For
- Sales reps who don’t want to sound like a robot
- Founders or recruiters juggling dozens of leads
- Anyone tired of copying and pasting follow-ups
If you need to send better follow-ups—without feeling gross—keep reading.
Step 1: Get Your Yesware Account Set Up (Don’t Skip the Basics)
You’ll need a paid Yesware account. The free trial is fine for testing, but scheduling sequences is a premium feature.
What you need: - A Gmail or Outlook account (Yesware only works with these) - The Yesware browser extension installed (for Gmail) or the add-in (for Outlook) - Access to your contacts or a CSV of leads
Pro tip:
If your IT team controls your email, you might need permissions to install extensions. Don’t wait until the last minute to sort this out.
Step 2: Understand the Two Ways to Schedule Follow-Ups in Yesware
Yesware gives you two main ways to send scheduled, personalized follow-ups:
-
Campaigns (formerly “Mail Merge”):
Best for reaching out to a list of contacts, with automated follow-ups and personalization fields. -
Templates + Reminders:
Good for one-off emails, where you want to be nudged to follow up manually if you don’t get a reply.
Honest Take:
If you’re serious about volume and not just following up with one or two people, use Campaigns. Reminders are fine, but they put the work back on you.
Step 3: Build Your Email Template (Without Sounding Like a Bot)
Whether you’re using Campaigns or just templates, don’t skip the groundwork here. Most templates are too generic and get ignored.
How to write a template that works:
- Start with a real opener (“Hope you're surviving Q2!” beats “Following up on my previous email.”)
- Use Yesware’s personalization fields:
{{First Name}}, {{Company}}, etc. These pull from your spreadsheet or contact list.
- Keep it short. Nobody reads a wall of text.
- Always have a clear ask (“Can you point me to the right person?” is better than “Let me know your thoughts.”)
What to ignore:
Yesware’s default templates are bland. Write your own, even if it takes an extra ten minutes.
Example:
Subject: Quick question, {{First Name}}
Hi {{First Name}},
I saw that {{Company}} is growing fast this year—congrats! I wanted to reach out to see if you’re the right person to talk to about [topic].
If not, could you point me in the right direction?
Thanks, [Your Name]
Step 4: Set Up a Campaign With Personalized Follow-Ups
Here’s where most people bail—because the interface isn’t super intuitive. Don’t worry, you’ll get the hang of it.
- Open Yesware in Gmail or Outlook and click on “Campaigns.”
- Create a new Campaign.
- Upload your recipients.
- Either add them one by one or import a CSV.
- Make sure your CSV has columns for all the personalization fields you want to use (First Name, Company, etc.).
- Write your initial email.
- Use the template you wrote in Step 3.
- Insert personalization fields by clicking the curly-brace
{ }icon. - Add your follow-up steps.
- Click “Add Step” to schedule a follow-up.
- Choose how long to wait before sending (e.g., 3 days after no reply).
- Write a new email for each step. Don’t just repeat yourself—offer something new, or show you did your homework.
- Preview and test.
- Use the “Preview” button to check that personalization fields are working.
- Send a test to yourself before launching.
Pro tip:
Don’t add more than 2-3 follow-ups. After that, you’re just annoying people, and Yesware’s deliverability drops if you get marked as spam.
Step 5: Schedule and Launch Your Campaign
- Pick your send times.
Yesware lets you send at specific times or use “Send in recipient’s time zone” if you have that data. Morning is usually best for B2B, but test for your audience. - Double-check everything.
Look for broken fields (Hi ,) and typos. - Click “Launch.”
Yesware will now start sending your emails, spacing them out according to your schedule.
What works:
Personalized fields, clean subject lines, and short emails.
What doesn’t:
Attachments, images, or overstuffed templates—these get flagged by spam filters more often.
Step 6: Monitor Replies and Adjust on the Fly
Yesware tracks who opens your emails, clicks links, and replies.
- If someone replies:
Yesware automatically removes them from future steps in the campaign. You don’t need to do anything. - If nobody bites:
Revisit your template. Sometimes a small tweak (like changing the subject line) makes a big difference. - Don’t obsess over open rates.
Opens are less reliable now thanks to privacy features in Gmail/Apple Mail. Focus on replies.
Pro tip:
If you keep getting “out of office” replies, adjust your timing or try different days of the week.
Step 7: Keep It Human—And Don’t Over-Automate
It’s tempting to set up a massive cadence and forget about it. Resist that urge.
- Check your campaigns once a week.
Update messaging, remove bad contacts, and look for patterns. - If you get a real reply, respond like a real person.
Don’t use a canned response—people can smell automation a mile away. - Less is more.
A few well-written, personalized follow-ups beat a scattershot approach.
Pro Tips & Common Pitfalls
What works: - Personalizing beyond just a name—reference a recent company announcement, their city, or a mutual connection. - Sending at natural times (Tuesday/Wednesday mornings, not Friday afternoons). - Keeping your follow-up short and polite (“Just bumping this up!” isn’t enough—offer value or a reason to reply).
What to ignore: - Overloading your emails with images or fancy formatting (triggers spam filters). - Blindly copying templates you find online (everyone’s seen them). - Scheduling more than 3-4 touches in a sequence—it gets creepy.
Common mistakes: - Not testing your campaign before sending (broken merge fields, yikes). - Forgetting to remove people who replied from your CSV before launching a new campaign. - Relying on Yesware analytics as gospel—treat them as hints, not facts.
Wrapping Up: Keep It Simple and Iterate
Yesware’s scheduling features can save you time, but they’re not a magic wand. The best results come from keeping your emails short, personal, and to the point. Start simple, test what works, and keep tweaking your approach. Don’t get lost in dashboards or overthink the tech—focus on sending messages you’d actually reply to.
Now go write a better follow-up. Your future self (and your prospects) will thank you.