How To Reach Decision-Makers Using Email and DMs: Lessons from Annika Ljaš Eilat

As Managing Partner at Exponential and one of the most experienced startup marketers in Estonia, Annika Ljaš Eilat has helped companies secure Fortune500 accounts, seven digit startup investments, and press coverage from Bloomberg to Forbes. Her approach? Thorough homework, being useful and keeping emails extremely short.

Most of your work life you’ve been in roles that require reaching out to decision-makers. What's the biggest mistake you see people make when they send emails?

I would say that the biggest thing is that people come off confusing. They say too much and ask too many different things in one email. In the startup world, they also tend to use words the other person doesn’t understand.

I love bringing the example from a client of mine. They had been emailing their customers for years with product updates, event invites, etc. After we redesigned their emails by removing most of the company branding; changed the subject lines and the tone of copy (made the emails conversational) – their customers started to email them back. With thorough comments and ideas. Never before had they received a responses like that.

You mentioned that you treat emails like face-to-face networking. What do you mean by that?

In person, you wouldn't walk up to someone and immediately jump to pitching them, right? You'd ask how they are, what they do and find a connection point. I believe that emails should be about the other person. Keeping them conversational is key.

After a polite beginning (Hi, how are you?, etc.), lead with a reference "XX said that we should connect and discuss…" or “like you said in your recent article...".

Subconsciously, the person thinks: “OK, this conversation makes sense”

You have an "unpopular opinion" about subject lines. What is it?

Say random things. Generic, headline type subject lines get buried. So do long subject lines, Sometimes, the most unexpected subject line works the best because it doesn’t feel staged. It feels human.

When we talk about your tone overall, being polite, sometimes witty is important, but never rude. Also, never expect anyone to respond. The moment you start counting emails you have sent them or mentioning that they haven't responded, you've lost. No one owes you anything.

Your thinking should be that no one is obliged to respond to any of your emails. If they do, it’s a privilege.

Speaking of multiple emails, you recommend sending up to 10. Isn't that too many?

In most cases, one email delivers nothing. Three emails in a sequence are great. Even better is a sequence of 7-10 very short emails sent in a sensible rhythm.

People don't respond because they simply missed your email. Never saw it. Successful people get hundreds, sometimes thousands of emails daily. Your job isn't to send one perfect email – it's to make sure your message gets noticed.

Sometimes they need to see your name pop up a few times before they think, "OK, I think that this person has something to say."

You mentioned jumping between different communication channels. What’s the deal with that?

This is something us Estonians especially worry about—we think people hate being contacted. Busy people simply don’t notice most of your attempts to reach them.

Sometimes I'll go from email to LinkedIn DMs. Sometimes from email to Whatsapp DMs. Communication happens across different mediums. You need to “meet” people where they're most comfortable at that moment.

In my case, it’s never a carefully planned system but rather a very human approach. I reach out to them via email and a bit later, I remember that I should mention one more thing. I send that via a DM. And by doing that, I open up an opportunity for them to chat with me. Instead of emailing. They can choose which medium they prefer to respond to. And when they prefer to do so.

People don't mind being contacted by someone who clearly has something valuable to say.

What's your formula for email length and sequence?

No email should be longer than five to seven sentences. Better if it's four. If you don’t believe me, send me your email and I will help you shorten it to five sharp sentences. Short emails are a joy to read. Busy decision-makers are often moving around.

The only exceptions are recurring newsletters like the legendary Benedict Evans' one or the weekly Memo written by Sten Tamkivi and Daniel Vaarik. These are indeed long emails but they follow a very clear structure, they are carefully thought-through and what’s most important – each paragraph provides some value to the subscriber.

In terms of sequencing, here is one technique I recommend testing. Alternate between four-to-five-sentence emails and one sentence emails. This rhythm makes the entire thread look more like a real conversation rather than a marketing sequence. It's more natural, more engaging. The one sentence emails usually are “I would love to hear your thoughts on this,” or “Did you have a moment to give it a thought?”.

You mention understanding what the other person gains. How do you research that?

This is fundamental. You need to understand their world. What are their key deliverables at work? What would help promote them or make their boss happy? Then you craft your message around that knowledge.

Also, avoid your industry jargon—use the words and phrases they use internally.

How to researcht it? I would say you go from deeply understanding the company and then their position and then in good detail, how your offering helps that company be more successful. This here is just an example of a sales situation, but the analog is similar to most use cases. You want to lead with what’s currently relevant to that person and their company/org, the trends that influence them.

What happens when your "perfect" email sequence doesn't work?

If a carefully planned email sequence fails, it's usually one of two things: you have a product-market fit problem, or you're approaching the wrong person.

The sequence is just the delivery mechanism. If the market doesn’t need your product or if you're talking to someone who simply isn't the right audience, even the best email copy won’t help.

Also, a helpful tip is probably that if what you are asking is relevant, you will get a very fast response to your first email. I have dozens of examples of reaching out to world-famous people like Sanna Marin, Garry Kasparov, etc.

”If your email or DM is relevant, you will get an answer within hours if not minutes.”

Any final advice?

Be patient and persistent, but never desperate. Remember that rejection and “ghosting” isn't personal—it's usually just timing or fit. And always do your homework. People can tell the difference between a thoughtful and a spray-and-pray approach.

Be useful. Approach every interaction with genuine value. Give before your expect to get.

No email should be longer than five to seven sentences. Better if it's four. If you don’t believe me, send me your email and I will help you shorten it to five sharp sentences. Short emails are a joy to read. Busy decision-makers are often moving around.