If you've got a list of leads and a product to sell, but you're tired of copy-pasting the same cold emails all day, you're in the right place. This guide is for anyone who wants to set up automated outbound email sequences in Letterfriend and actually get replies—without nuking your sender reputation or annoying everyone in your database.
We'll skip the sales pitch and get right to what works, what doesn't, and how to avoid rookie mistakes. Let's get your outreach running on autopilot (the smart way).
Why Automate Outbound Email Sequences (and Why It Sometimes Backfires)
Automating outbound emails can save hours every week and keeps you from dropping leads through the cracks. But here's the truth: badly automated outreach is worse than no outreach at all.
- Good automation: Feels personal, respects timing, and keeps your inbox open for replies.
- Bad automation: Spams people, torpedoes your domain, and fills your inbox with “unsubscribe me” replies.
The goal here is targeted, respectful automation—not shotgun blasts. That’s what Letterfriend is built for, but you still have to set it up right.
Step 1: Get Clean, Targeted Lead Lists
Before you touch Letterfriend, clean up your list. Automation will amplify whatever you feed it, so garbage in means garbage out (only faster).
What works: - Start small. Quality over quantity. Ten great leads are better than 1000 “maybe” emails. - Verify emails. Use a tool to make sure addresses are real and not spam traps. - Add context. Name, company, recent news—anything you can use to make emails less generic.
What to ignore: - Buying giant lists. This is a quick way to get your domain blacklisted. - Scraping everything that moves. If you wouldn’t email them by hand, don’t automate it.
Pro Tip: If you’re not sure if your list is clean, run it through an email verification tool before uploading.
Step 2: Draft Emails That Don’t Suck
Letterfriend can send emails, but it can’t make them good. That’s your job.
Keep it simple: - Short subject lines. “Quick question” works better than “Innovative Solutions to Optimize Your Workflow.” - First line: Show you know them. “Saw you just launched X. Congrats!” beats “Dear Sir or Madam.” - One clear ask. Don’t cram in three calls to action. - Ditch the fluff. You’re not writing a novel.
What works: - Using merge tags (Letterfriend supports {{first_name}}, {{company}}, etc.) for personalization. - Sounding like a human. “Would love to chat next week” is better than “Kindly revert at your earliest convenience.”
What to avoid: - Templates copied off the first page of Google. - Overly formal or robotic language. - Writing for your boss instead of your prospect.
Pro Tip: Send your draft to yourself first. If it feels cringe to read, rewrite it.
Step 3: Set Up Letterfriend and Import Your Leads
Head to Letterfriend and sign up or log in. The dashboard is straightforward, but here’s what you need to know:
- Import Your List: Upload your CSV. Make sure columns match what you’ll use in your email (like first name, company, etc.).
- Map Fields: Letterfriend will ask you to map your CSV columns to its fields. Double-check this—otherwise your “Hi {{first_name}}” turns into “Hi Company ABC.”
- Tag or Segment: If you want to send different emails to different segments, tag your leads now.
What works: - Smaller batches to start. If something breaks, you won’t burn your whole list at once. - Double-checking field mapping. It’s boring but worth it.
What to ignore: - Uploading huge lists “just to see what happens.” You’ll regret it.
Step 4: Build Your Email Sequence
Now the fun part. Letterfriend lets you set up multi-step sequences—think initial outreach, gentle follow-up, maybe a breakup email if they ghost you.
How to do it: 1. Create a Sequence: Give it a name you’ll remember. 2. Add Steps: Write your first email, then add follow-ups. You can set delays (e.g., wait 3 days before next email). 3. Use Personalization: Drop in merge tags for names, companies, etc. Don’t overdo it—one or two personal touches is enough. 4. Set Conditions: Only send follow-ups if they don’t reply. It’s basic, but skipping this leads to embarrassing double-emails.
What works: - Two or three follow-ups max. After that, you’re probably just annoying people. - Testing each step by sending to yourself first. - Spacing emails a few days apart—nobody likes five emails in five days.
What to avoid: - “Breakup” emails that try to guilt-trip prospects (“I guess you don’t care about saving money…”). Nobody likes these. - Overcomplicating with too many branches and conditions. Start simple.
Pro Tip: Write your follow-ups as if you’re writing a quick note, not a sales pitch. “Hey, just checking if you saw my last note. Let me know if you’re interested.”
Step 5: Set Sending Limits and Warm Up Your Domain
This is where most people mess up. If you blast 500 emails from a brand new account, Google’s spam filters will notice.
How to keep your emails out of spam: - Start slow: 20-50 emails per day is plenty to start. - Ramp up gradually: Add more each day, but never jump from 20 to 200 overnight. - Warm up your sending domain: If your domain is new, consider using a tool or just send manual emails for a week or two first.
What works: - Monitoring open and reply rates. If you see a sudden drop, pause and check what’s up. - Using your own domain (not Gmail, Yahoo, etc.) for outreach.
What to ignore: - “Spray and pray” strategies. - Sending from free email accounts.
Pro Tip: If you see a lot of bounces or “message not delivered” errors, stop immediately and check your list and domain health.
Step 6: Monitor, Reply, and Iterate
Automation isn’t set-and-forget. If people reply and you don’t answer, you’re wasting effort.
What to do: - Check replies daily. Respond quickly—automation just gets you to the conversation, it doesn’t close the deal. - Track which emails get opens and replies. Letterfriend gives you stats, but don’t obsess—look for obvious patterns. - Tweak your sequence. If a step gets zero replies, rewrite it or cut it.
What works: - Personal follow-ups after someone replies to the sequence. - Testing one change at a time—don’t overhaul everything at once.
What to ignore: - Chasing vanity metrics (opens, clicks) if nobody replies. - Getting fancy with A/B tests before you’ve run a full sequence to even a dozen leads.
Pro Tip: If you’re not getting responses after two weeks, your list or your message is off. Change one, not both.
Step 7: Stay Legal and Respectful
Don’t get yourself blacklisted (or worse, sued).
Minimum you should do: - Make it easy to unsubscribe. Letterfriend can handle this with a link—use it. - Don’t email people who’ve opted out. - Keep your messages honest. No fake “Re:” subject lines.
What works: - Transparency. Tell people who you are and why you’re reaching out. - Quickly removing anyone who asks to be unsubscribed, even manually.
What to ignore: - Advice that says you can spam anyone as long as it’s “B2B.” Laws vary, and people have long memories.
Quick Recap: Keep It Simple, Iterate, and Don’t Be a Robot
Automating outbound emails in Letterfriend can save you time and help you reach more leads, but only if you keep things personal, respectful, and small to start. Don’t chase scale before you have a message that gets replies. Clean lists, short sequences, and real conversation always beat “spray and pray.”
Set it up, send a few, watch what happens, and adjust. That’s how you get real leads—without burning your reputation or inbox.
Now go write something worth replying to.