You’re in B2B sales. You’re tired of spray-and-pray emails that get ignored. You want your outreach to actually sound like a human wrote it—but you also need to reach way more people than you could ever write to by hand.
This guide is for you. It’s about using Letterfriend to personalize your sales outreach so it stands out, gets read, and doesn’t make you feel like a robot. I’ll walk you through a practical approach that actually works (and call out what doesn’t).
Why Personalization Still Matters (Even When Everyone’s Doing It)
Let’s be real: “personalization at scale” is one of those phrases that gets thrown around a lot. But most of what passes for personalization is just someone’s name auto-inserted in a template. Prospects can spot this a mile away.
What actually works? Messages that sound like you did a little homework and actually care. The good news: you don’t need to write a novel for every prospect, and you don’t need to stalk everyone’s LinkedIn for 20 minutes. But you do need to treat people like, well, people.
Letterfriend is built to help with that. But it’s just a tool—you still need a process and some good judgment. Let’s get into it.
Step 1: Start With a Clean, Segmented List
If you’re reaching out to random companies with no rhyme or reason, no amount of personalization tech is going to help.
What works: - Segment your list by real criteria. Think: industry, company size, use case, trigger events (e.g., just raised a round, recently launched a new product). - Clean your data. Bad contact info = wasted effort. Spend the time to get this right.
What doesn’t: - Giant, undifferentiated lists. You can’t write a message that’s relevant to everyone. - Using data from sketchy sources. You’ll get bounced emails, angry replies, or worse.
Pro tip: The more tightly you segment, the easier it is to write messages that sound personal and relevant.
Step 2: Don’t Over-Automate the Research
Letterfriend can pull in info from LinkedIn, company sites, and more. That’s handy, but don’t fall for the trap of stuffing every data point you can find into your messages.
What works: - Pick 1-2 specific details to personalize. Maybe it’s a recent blog post they wrote, a mutual connection, or something about their product. - Set up clear rules: e.g., “If they’re in SaaS, mention their pricing page; if they’re in e-commerce, mention their latest promo.”
What doesn’t: - Auto-inserting laundry lists of company facts. It feels fake and makes your email a mess. - Generic “I see you’re the CEO at CompanyName”—everyone does this.
Pro tip: Use Letterfriend’s preview feature. If your insert looks robotic or forced, it probably reads that way too.
Step 3: Write Templates That Don’t Feel Like Templates
This is where most “personalization at scale” goes to die. If your base email sounds stiff or salesy, no amount of custom fields will fix it.
What works: - Short, direct, and human. Write like you’d talk to someone at a conference, not like a marketing robot. - Keep your templates modular. Use 1-2 places for real personalization (“saw your recent launch of {{ProductName}}”) and keep the rest flexible. - Test your own emails. Would you reply to this? If not, rewrite.
What doesn’t: - Writing a single “catch-all” email for every segment. It’ll sound generic. - Overusing curly-brace fields (“Hi {{FirstName}}, I see you’re the {{Title}} at {{CompanyName}} in {{City}}.”). It’s obvious.
Pro tip: If you can’t tell which part is the personalized one at a glance, neither can your prospect.
Step 4: Use Letterfriend’s Personalization Features—But Don’t Rely on Them Blindly
Letterfriend can automatically suggest snippets and pull in relevant info. This is where the magic should happen—but you’ve got to check its work.
What works: - Review snippets before sending. Automation is great, but mistakes slip through. - Customize your fallback text. If Letterfriend can’t find the right info, have it insert something natural (not “N/A” or “Unknown”). - A/B test your approach. Try different kinds of personalization—does referencing a prospect’s recent funding round work better than mentioning mutual connections?
What doesn’t: - Sending without reviewing. Typos, wrong company names, or copy-pasted errors are embarrassing. - Overengineering. Don’t set up 15 fields of personalization if you can’t maintain them.
Pro tip: Sometimes “lightweight” personalization (“Congrats on the new role!”) beats a forced, overly specific one.
Step 5: Set Realistic Volume and Quality Goals
The temptation is to blast as many emails as possible. Resist. Even with Letterfriend, more isn’t always better.
What works: - Set a daily send limit. This gives you time to review and tweak as you go. - Track replies, not just sends. If people aren’t engaging, it’s time to adjust. - Refine your segments and templates as you get feedback. Outreach is never “set it and forget it.”
What doesn’t: - Thinking you can do true personalization for hundreds of prospects a day. Quality slips fast. - Only measuring success by volume. You want conversations, not just “delivered” stats.
Pro tip: Most teams see better results from sending 20 great emails than 200 mediocre ones.
Step 6: Follow Up Like a Human
Letterfriend can automate follow-ups, but don’t just send endless “bumping this to the top” emails.
What works: - Vary your follow-up content. Reference your previous email, but add something new (a resource, a question, a comment on recent news). - Keep it short and polite. If they’re not interested, don’t hound them. - Set a limit. Two or three touchpoints is usually enough—after that, move on.
What doesn’t: - Generic follow-ups (“Just checking in!”) with no added value. - Pestering people who’ve clearly opted out or ignored you repeatedly.
Pro tip: Personalization isn’t just for the first email. A small, relevant detail in a follow-up can make all the difference.
What to Ignore
There’s a lot of hype (and a lot of bad advice) out there. Here’s what you can safely skip:
- Don’t believe claims of “100% automated personalization.” No tool gets it right every time.
- Ignore tools that promise instant results. Outreach is a process.
- Don't stress over tiny personalization tricks (“use emojis in subject lines!”). Focus on substance.
Wrapping Up: Keep It Simple, Test, and Tweak
Don’t overthink it. Great outreach is about relevance, not just tech tricks. Use Letterfriend to save time, but don’t let it replace your judgment.
Start small, measure what actually works, and keep fine-tuning. If your emails sound like you and get replies, you’re on track. And if you screw up? Just own it and move on. That’s more human than any template could ever be.