As a CTO or senior technical leader, you know that climbing the career ladder isn’t just about coding, managing teams, or deploying systems anymore. It’s about positioning yourself for the next big opportunity — whether that’s moving into a CIO role or leading a new, cutting-edge tech initiative. The problem is, that the most exciting roles are often hidden. They don’t show up on job boards, and you certainly won’t find them in your LinkedIn feed. So, how do you discover these hidden gems?
In my latest podcast episode with Oliver Degnan, CIO, and former CTO, he shares an incredible hack that helps senior technical leaders like yourself find and land those elusive executive roles. If you're ready to unlock the secret behind confidential searches for CIO positions, this blog post is for you!
You can watch the video on YouTube or below:
Here’s the truth: The best jobs for executives like you are rarely advertised. The companies looking for top-tier talent are conducting confidential searches, often with retained search firms. This means that unless you're well-networked or actively seeking out these hidden opportunities, you could easily miss them.
But Oliver shared a little-known trick during our conversation that can give you the upper hand.
One of the best strategies Oliver discussed is how to find executive positions using LinkedIn Sales Navigator. This tool is often overlooked by senior leaders who focus more on the technical aspects of their work than on networking and job hunting. But if you're serious about taking your career to the next level, it's time to change that.
Oliver explained it like this:
“I found 22 people who had been in their current CIO role for only a month or two. I simply clicked on their profiles to see where they were previously, and then I called up human resources. You can say, ‘Hey, I heard you have a sensitive search going on to replace your CIO.’ Usually, they’ll give you the details — whether it’s with an executive search firm or directly through their HR department.”
This technique allows you to insert yourself into the conversation before the role is ever posted online — if it even gets posted at all.
The beauty of this approach is that it places you ahead of the competition. Instead of competing with hundreds of applicants, you're part of a much smaller pool of candidates, often handpicked by the company's decision-makers. This gives you a far better chance of landing the role — especially if you follow Oliver's advice about approaching the company strategically.
“Once you have the company on the phone, make sure you know their previous CIO’s name,” Oliver advises. “Say something like, ‘I’m calling for the replacement for Mark Anderson, who left not too long ago. Who’s leading your search right now?’ It’s all about positioning yourself as an insider.”
By positioning yourself as someone who already understands the company’s needs and challenges, you’re not just another resume in the pile — you're someone they want to talk to.
While Sales Navigator is a fantastic tool, another critical aspect of this strategy is networking. As a senior technical leader, you should always be nurturing relationships with peers, mentors, and industry insiders. Oliver emphasized the importance of maintaining these relationships over time.
“I have a Google sheet with a couple hundred contacts that I ping every few months,” he shared. “You don’t want to be forgotten by people who might help you land your next big role.”
It might sound simple, but staying in touch with key people in your network is often the difference between getting introduced to a job opportunity and being left in the dark.
Make a habit of regularly reaching out to old colleagues, mentors, and even people you’ve met at conferences. It doesn’t need to be a lengthy conversation. A simple check-in or sharing an article you think they’d find interesting can go a long way.
Another important takeaway from the interview is the need for a solid strategic plan. If you’re aiming for a leadership position, you can’t just send out resumes and hope for the best. As Oliver puts it:
“Your number one job right now is to find a job. But it’s more than just a job — it’s your company. You are the product, and you need to run your job search like a business.”
This means researching the companies you’re targeting, understanding their current challenges, and knowing how your skills and experience can address those challenges.
Let’s summarize some key takeaways from Oliver Degnan’s advice for CTOs and senior leaders looking to level up their careers:
Use LinkedIn Sales Navigator to discover hidden executive roles. The best opportunities are often not advertised, and you need to proactively search for companies that are quietly replacing their CIOs or other senior leaders.
Position yourself as an insider. When you call HR or an executive search firm, know the name of the previous CIO and demonstrate that you understand the company’s needs.
Leverage your network. Keep in touch with your industry contacts regularly. Your next job might come from a conversation with someone you haven’t spoken to in a year.
Approach your job search like a business. Research companies, understand their challenges, and present yourself as the solution. Don’t just wait for opportunities to come to you.
The tech world moves fast, and if you're looking to transition from CTO to CIO, you need every advantage you can get. Implementing Oliver Degnan’s strategies can help you uncover hidden opportunities and put you on the radar for executive-level roles. Feel free to reach out to Oliver on LinkedIn or visit his website for more insights.
Good luck, and remember: the next step in your career is out there — you just need to know where to look!