How to Email A Prospect Who Started A New Job

It's common to send a cold email when a prospect starts a new role. However, most of these emails are ineffective. Here's why and how to write a trigger event email that gets replies.

We’ve all been there — you start a new job and immediately receive a flood of cold emails.

This is what’s known as a sales trigger event.

It’s an occurrence that creates the opportunity for a prospect to potentially be more receptive to the solution you’re selling. It’s a well-intentioned tactic, but most of these emails fall flat.

It usually goes something like this:

The seller reaches out to the prospect cold.

They lead with a nice compliment about “me,” but it’s not truly personalized. (more on this later)

They politely ask me to share my priority or challenge in my new role.

Then they ask me for a quick reply.

Why Some Sales Trigger Emails Don’t Work

I can tell the seller is a nice person; they’re being polite. But I can also tell they’ve been misled — taught or trained by their boss because they think this tactic “works.”

This is what their boss didn't tell them:

I’m not an executive. Yet I still receive many of these emails when I start a new role.

If I replied to all of them, I’d probably get fired for getting zero work done.

Here’s the thing: Being polite is not a differentiator. It's table stakes.

Let’s flip this scenario to your perspective as a seller.

When sending a cold email, you’re inserting yourself in your buyer’s day and asking for their time and attention. They receive a lot of emails. You have to compete for attention in the inbox. One major way to stand and earn a reply is to write an email that makes it easy to reply.

If your reader doesn’t know who you are or your company, why would they spend time educating you on their priorities and challenges? That’s a high-effort ask.

How to Send a Sales Trigger Email That Works

Here’s what you can do instead:

Craft a hypothesis about a timely problem your buyer might be facing. You can do this through effective personalization research. Your goal is to present context and observation in your first-touch email.

Your email should immediately answer: Why are you reaching out? And what personal observation did you find in your research that makes you think you might have a solution to help them? (Here are more frameworks on how to achieve this.)

Share a unique point of view on what others in a similar role as your reader may not know about the root cause of the cost of their potential problem.

End with a low-pressure close and a call to conversation. (“Either way, congrats on the job. Really cool to watch how [company] is doing [x].”)

It’s all right if you’re wrong about the problem. You can try a different hypothesis in the following email. Your goal is to get a reply and start a conversation.

This approach to a trigger event shows that you have something to add to the conversation. You’re showing you’ve done your research, taken time to get to know them, and given sincere thought to why you’re reaching out to them and why now.

Cold emailing isn’t easy. Behind most bad outreach is a company template, training, or rule the seller is told to follow. Break the status quo and reach out like a human.

Video more your style? Jen recently shared more on this topic with our friends at UserGems.

How to Email A Prospect Who Started A New Job