If you sell to other businesses, you already know: most deals don’t close after one email. Or two. Or sometimes even ten. Following up is where deals happen, but it’s also where most salespeople drop the ball. If you’re tired of manually chasing leads, this guide is for you.
We’re going to walk through — step by step — how to automate your follow-up emails for B2B sales using Maildoso workflows. No fluff, no magic bullets, just a practical look at what actually works (and what to skip).
Why Bother Automating Follow-Ups?
Let’s be honest: sending follow-up emails is boring, repetitive, and easy to forget. But it’s also the difference between a pipeline that moves and one that dies on the vine. Here’s why automating makes sense:
- You save hours every week — and avoid letting leads slip through the cracks.
- You stay consistent — and consistency wins deals over time.
- You can test and tweak — see what actually gets replies, instead of guessing.
But automation can backfire if you sound robotic or blast out the same tired message. We’ll get to that.
Step 1: Get Your List in Order
Automation is only as good as your data. If your contact list is a mess, your emails will be too.
What you need: - Names, job titles, company names, and (of course) email addresses. - Optional: LinkedIn URLs, industry, last contact date, notes.
How to prep: - Use a spreadsheet or your CRM to export your list. - Clean up duplicates, fix obvious typos, and remove junk contacts. - Segment by stage (e.g., “first contact,” “waiting reply,” “demo booked”).
Pro tip: Don’t overthink segmentation. Two or three basic segments (like “cold” vs. “warm”) beat a dozen you’ll never use.
Step 2: Map Your Follow-Up Sequence
Before you touch Maildoso, sketch out what your follow-up should actually look like. Otherwise, you’ll end up automating a mess.
Typical B2B follow-up sequence: 1. Initial email — Your intro or pitch. 2. Follow-up #1 (2-3 days later): Short, polite nudge. “Just checking in…” 3. Follow-up #2 (4-5 days later): Add value. Share a resource, ask a question. 4. Follow-up #3 (1 week later): Last attempt — keep it brief, maybe add a little humor or a “should I close your file?”-type prompt.
What to skip: - Anything that’s just “bumping this to the top of your inbox” over and over. - Overly aggressive or needy messages. - Sequences longer than 4-5 emails. At that point, you’re probably just annoying them.
Step 3: Write Real Emails (Not “Templates”)
This is the part most people screw up. If your emails sound canned, you’ll get tuned out. Automation doesn’t mean impersonal — it means not repeating yourself.
How to do it:
- Write each email as if you’re sending it to a real person.
- Use simple mail merge tags (like {first_name}, {company}) for personalization.
- Keep it short. If you can’t read it aloud in 20 seconds, it’s too long.
Example follow-up:
Subject: Any thoughts, {first_name}?
Hi {first_name},
Just wanted to check if you saw my note about {pain_point}. Happy to chat or send over more info if helpful.
Thanks, [Your Name]
Pro tip: Go back and remove any line that sounds like something you’d ignore yourself.
Step 4: Set Up Your Maildoso Workflow
Now, into the actual automation. Here’s how to set up a workflow in Maildoso:
- Log in and go to “Workflows.”
- Create a new workflow. Give it a clear name, like “B2B Follow-Up Sequence Q2.”
- Import your contact list — either upload a CSV or sync with your CRM.
- Build your sequence:
- Add your initial email as the first step.
- Set delays between steps (e.g., 3 days, 5 days).
- Add your follow-up emails as the next steps. Use mail merge tags for personalization.
- Choose triggers and conditions:
- For B2B, set your workflow to stop if the contact replies. No one wants to get a follow-up after they just responded.
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Optionally, set rules (e.g., skip weekends, only send during business hours).
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Test your sequence:
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Send the sequence to yourself first. Check for weird formatting, broken merge tags, or embarrassing mistakes.
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Activate the workflow — and monitor for any issues.
What to ignore: - Don’t waste time with fancy branching (“If they click, send this; if they open, send that”). Most B2B leads don’t click much, and you’ll just make things complicated. - Don’t go crazy with “AI” copy suggestions. They usually sound bland.
Step 5: Monitor, Tweak, and Don’t Annoy People
Automation isn’t “set it and forget it.” You need to pay attention to what’s working and what’s not.
What to watch: - Open rates: Are people actually reading your emails? - Reply rates: This is what really matters. - Unsubscribes or spam complaints: If these spike, dial it back.
How to improve: - Change your subject lines — boring or spammy ones get ignored. - Shorten your emails. Seriously, almost everyone writes too much. - Try sending at different times, but don’t obsess over “the perfect hour.”
Pro tip: If someone asks to stop hearing from you, make sure you actually take them off your list. Nothing kills trust faster than ignoring an opt-out.
What Works, What Doesn’t, and What to Ignore
Works: - Personalization (even just a name/company) gets more replies. - Following up 2 or 3 times — most sales happen after at least one nudge. - Keeping it simple: fewer steps, fewer bells and whistles.
Doesn’t work: - Long, essay-length emails. - Templates copied from some “guru” site. - Hitting people with daily emails.
Ignore: - Overhyped “AI” features that promise to write your emails for you. They’re not there yet. - Overly complex workflows with a dozen branching paths. You’ll just confuse yourself.
Wrapping Up: Keep It Simple, Iterate, Don’t Overthink It
Automating your B2B follow-ups with Maildoso isn’t hard — unless you make it hard. Set up a basic workflow, write real emails, and check your results every couple of weeks. If you get stuck, strip things back and focus on sending messages you’d actually reply to.
Don’t chase perfection. Just get your follow-ups out there, see what works, and tweak as you go. Most sales teams are still fumbling with spreadsheets and sticky notes — you’ll be ahead of the game just by getting this set up and running.
Now, go make your inbox (and your pipeline) a little less painful.