How to Get a CEO’s Attention During a Job Search
Cold outreach to the company of your dreams
Most job applicants simply apply by submitting their resumes. A method for greatly increasing your likelihood of getting a job (or at minimum getting a response) is to go direct—find a way to get their attention some other way.
But trying to get the attention of busy people is not always easy. In fact, it’s often quite challenging and requires some creative thinking to successfully stand out.
That’s why we got in touch with Next Play community member Mark Josephson. Mark is a CEO/leadership coach who has 30+ years of experience building companies and working with people in tech. He has sold several companies, and importantly been a VERY BUSY PERSON, so he has an understanding of what it’s like to scan through hundreds of job applications.
From his personal experience, we asked him to write a practical guide to “cold emailing a busy CEO/hiring manager” — we think you will find it tactical and useful as you explore new opportunities.
How to Get a CEO’s Attention During a Job Search: Cold Outreach to the Company of Your Dreams
Getting a CEO’s attention isn’t easy. Their time is limited, their inboxes are overloaded, and they’re constantly prioritizing a million things that aren’t you. But that doesn’t mean you can’t break through—if you’re strategic, thoughtful, and add value at every step.
This guide walks you through exactly how to do that, with tactical steps, real examples, and screenshots you can use as a reference.
Start before you send that connection request
Most people get this wrong. They fire off a cold LinkedIn request or an email with their resume attached, hoping for a miracle. That’s not how this works.
Instead, you need to show up before you ever reach out.
Step 1: Follow the CEO and the Company on LinkedIn
Find the CEO’s LinkedIn profile and hit “Follow” (don’t connect yet!).
Follow the company’s page, and if they have key execs or hiring managers active on LinkedIn, follow them too.
Step 2: Thoughtful Engagement—Commenting and Sharing
Comment with insights: Instead of just liking their posts, add thoughtful comments that demonstrate industry knowledge or appreciation.
Post Example: A CEO shares an update about launching a new pricing tier for SMB customers.
Comment Example:
“Love this move. We launched a similar mid-tier plan at ABC Corp. and saw a big lift in retention among early-stage users. Curious how you're thinking about balancing price vs. feature depth for this audience—always a tricky line!”
Share with value-add: If the CEO or company posts something relevant, share it with your take on why it’s important.
Post Example: A company publishes a blog about how AI is impacting their customer onboarding.
Share Example Caption:
“This is a smart breakdown of how AI can make onboarding faster and more human at the same time. We learned something similar when testing automated chat support—speed and empathy don’t have to be a tradeoff.”
Step 3: Make Multiple Touchpoints
Don’t just engage with the CEO—comment on posts from the exec team, hiring managers, and even the company’s official account. This builds familiarity before you ever send a request.
Find a Warm Path In
A direct intro is always better than a cold email. Here’s how to increase your odds of getting one:
Step 1: Identify Potential Connectors
Board members, investors, or mutual connections: A warm intro from someone they respect can shortcut the process.
Tap into past relationships: Former colleagues, industry connections, or event attendees may have a path in.
Step 2: Ask for an Introduction the Right Way
Instead of a generic request, make it easy for your connector to help you. Provide them with the right context and a forwardable email.
The Email CEOs Actually Want to Read
If you’re cold-emailing a CEO, you need to do more than just express interest—you need to add value.
Ask yourself: What can I share that they’d actually find useful?
This could be:
A sharp observation about their business.
An insight from a similar challenge you’ve tackled.
A well-informed perspective on an opportunity in their space.
If you can’t come up with something compelling, that’s a sign you’re not ready.
The Right Way to Follow Up
One email is rarely enough. If you don’t get a response:
Wait a week and send a polite, value-added follow-up.
If you still don’t hear back, engage with their content again—commenting on a recent post, for example—before attempting another outreach.
If they say no or don’t respond after multiple attempts, move on. CEOs are busy, and no response is a response.
Final Thoughts
Getting a CEO’s attention isn’t about luck—it’s about strategy. Do your research, engage thoughtfully, and lead with value. If you can demonstrate that you understand their business, respect their time, and have something worthwhile to say, you’ll be far ahead of the pack.