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Finding Your Next Great CIO Job, Step One: Knowing When It’s Time to Leave

Martha Heller
By Martha Heller

Jan 28, 2026

In this, the first article in a series guiding IT leaders to find a role that matches both your interests and abilities, Heller CEO Martha Heller explains how you know when it’s time to change jobs.

Whether you’re pursuing your first CIO job, or you’re already a CIO looking for a new challenge, you need to think strategically about your job search to secure a position that is the best match for your interests and abilities. In this series of articles, I will provide a guide designed to get you off to the strongest possible start, with proven tips and advice for every stage of the job search process.

The first step in securing a new role is to recognize when it is time to leave your current position. There are risks when leaving one company for another. (Out of the frying pan and into the fire.) So, you want to be certain that you are ready to leave before you start circulating your resume.

Here are six signs that the time is right to make a move:

1.   You’ve hit a ceiling. 

Maybe you’re a divisional CIO and your boss, the global CIO, isn’t going anywhere for a while. Or perhaps you are a director of application development and rather than getting promoted, you’ve just gotten a new boss. If you’re ready for growth, but you see a ceiling, it may make sense to look elsewhere for opportunities.

2.   You’re a turnaround CIO in maintenance mode. 

Most CIOs thrive on driving change. If you were hired to fix IT, and the CEO does not want to invest in IT innovation, you will get bored. These days, it is hard to imagine a CEO not seeing endless opportunities for IT investment, but they are out there. If you are working for one of these CEOs, by all means, work hard to make a strong business case for innovation. But if your CEO cannot see the light, move on. If maintenance isn’t your thing, it’s time to go out and find another big, hairy problem to solve.

3.   Your reporting structure changes.

If you’ve been reporting to the CEO, and she decides you should report elsewhere, that’s a clear signal that the company’s IT priorities are changing. If you suddenly find yourself reporting to the CFO, who is more focused on cutting IT costs than investing, it may be time to get out. Many happy and successful CIOs report to CFOs, but when your role gets demoted, you need think hard about what that means. If it means that IT has moved from value to cost, or from strategy to operations, you may need to move as well.

4.   Your company is for sale.

If your company is on the block, you may face one of three scenarios:

  • You’ll be asked to downsize your organization to cut costs before the sale. 
  • You will be offered a package and asked to leave.
  • Once the sale takes place, the acquiring company decides to replace you with its CIO.

Now, a sale could open up new opportunities for you in the new, larger company. But you might not love the new culture or management team. Or perhaps you will. Either way, it is best to have a job search under way while you wait to find out.

5.   You don’t like your new boss.

When you first took your current job, you were probably excited to work for the person hiring you. If that person leaves, and you don’t see eye to eye with his or her replacement, it may make sense to begin a job search.

Perhaps you thrive in a consensus-driven organization, and your new boss’s “command and control” approach doesn’t work for you. As you spend the time doing your best to nurture the new relationship, you should also be evaluating new opportunities.

6.   Your company or industry is failing.

Staying with a dying company that cannot reinvent itself to survive will give you valuable experience, build character, and teach you enough lessons to fill a book. But you’re not obligated to go down with the ship. Once you’ve gained all of the experience you can, it may be time to look elsewhere. If your whole industry is in trouble, consider moving to an industry in growth mode.

Keep in mind that a job search may take six months or more, particularly if you’re limiting it based on geography, or you’re targeting a specific industry or narrowly defined field. Other articles in this series will discuss additional steps you can take in the process to land a new position. In the meantime, if signs point to a less than positive future in your current organization, start your job search now.

Martha Heller

Written by Martha Heller

Martha Heller is a widely followed technology talent thought leader and the CEO of Heller, a specialized technology executive search firm for the data economy. Martha is the author of two books which have shaped the technology talent discussion: Be the Business: CIOs in the New Era of IT, and The CIO Paradox: Battling the Contradictions of IT Leadership.