Longer Job Searches, Faster-Moving Tech: Odyssey Information Services on Staying Relevant

The AI headlines are hard to ignore. We're bombarded by them.

In the last month alone, I've had several conversations with mid-level to executive level job seekers in the tech industry that are struggling to find a new job.

It's not just the layoffs. It's what comes after. Tech workers now spend 3 to 9.7 months searching for their next role. That is an extreme test of resilience, patience and self-belief.

But headlines are not the full picture. I spoke to tech hiring experts about this on the Tech Legacies podcast.

This one was a roundtable with three leaders from Odyssey Information Services: Jon Hibbs (CEO), Ben Coan (Managing Director of Managed Services), and Kristin Hughes (Director of Recruiting). They've been in tech staffing and services for decades, and they're watching this market in real time.

Here's what stood out:

No matter how much technology evolves, hiring is still a people's decision.

Jon has been running Odyssey for 25+ years. Technology has changed constantly. What hasn't?

"Clients want partners that really understand their environment and candidates want someone that represents them really well, not just a transaction."

Trust doesn't scale through automation. It compounds through relationships. Go and build new relationships or revitalize your old ones.

The market isn't broken. It's shifting.

Kristin is on the front lines, hearing from candidates every day. What she's seeing is not a collapse… it's a reset.

"It's not necessarily a lack of hiring. I think it's more about a shift in priorities… it's become much more intentional."

There are roles still being filled regularly, including security, cloud, and finance. What's changed is that employers are asking harder questions about every hire.

Stop applying to everything.

One of the most direct pieces of advice Kristin shared: if you've submitted 250+ applications and aren't hearing back, the strategy itself is the problem.

"Please stop right now. That is only going to lead to frustration… apply to 10 jobs that are extremely targeted and take the time to do the research."

Know your why. Reach out directly. Be creative. One candidate she worked with got an internal posting at her dream company by taking a frontline job there first. She then applied for a corporate job through their internal portal. Unconventional? Yes. But it worked.

Most companies don't realize how much risk is hiding in their own legacy system.

Ben heads up managed services at Odyssey. What he sees across client environments is consistent: legacy platforms running mission-critical operations, little to no documentation, and a workforce aging out. Excel sheets are still more prevalent than we think. Managed services is how Odyssey steps in, by embedding teams that handle the infrastructure so clients can focus on their actual business.

His longest client relationship started with one consultant on a server migration. A decade later, Odyssey runs two network operation centers for that same organization.

Here's something to consider. While everyone is chasing AI, there's still a huge need to integrate, update and maintain legacy systems, as well as data clean ups before any form of AI is possible.

What legacy really means.

At the end of the conversation, I asked all three what legacy they want to leave behind. They each answered independently - and landed in almost exactly the same place.

Jon: "Treat people the right way, not just in the big moments, but in the everyday ones. And if you go with that principle, the legacy will take care of itself."

Ben: "Do what you're going to say. Be all in.

Kristin: "That I did what I said I was going to do, that I was always authentic and that if I did something, I was going to do it 100%."

That kind of alignment doesn't happen by accident. It's culture.

Watch the full episode here.

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The other side of the coin …

I came across a New York Times piece recently that stopped me mid-scroll. While companies like Meta and Coinbase have been cutting roles in the name of AI efficiency, Box, a Silicon Valley software maker, has created 13 new types of jobs because of AI. Titles like AI architect, AI solutions manager, AI platform leader. They expect to have more employees, not fewer, by early next year.

CEO Aaron Levie's explanation was simple: selling AI to customers requires more people. And the internal productivity gains are generating new work that also requires more people.

This doesn't contradict what Kristin described about the market slowing down. Both things are true at once. Some roles are disappearing. New ones, and ones that didn't exist two years ago, are emerging. The people who navigate that well will be the ones who stay curious, build real skills, and keep investing in relationships.

That's always been the answer. AI just made it more urgent.

Visibility drives opportunity.

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Thank you to our Tech Legacies sponsor, CG Infinity!

Huge thank you to ​CG Infinity​ for sponsoring our podcast so we are able to feature these tech leaders with their perspectives and insights. Follow their company page to learn about their tech consulting services and #peoplefirst culture.

Looking for a heart-centered executive coach in the tech industry?

You're already knowledgeable and experienced in your career. The next level is about leadership, developing teams and overcoming self-limiting beliefs. Shaunna Black is now a sponsor of our podcast and she can help you on that growth trajectory. I highly recommend her services. Connect with her to learn more.

Struggling to find the right candidates and resources?

Check out our sponsor, Odyssey Information Services, a technology consulting, staffing, professional and managed services firm with a dedicated team, many of them deeply established employees that believe in building long-term relationships with clients and candidates. Click on this link for the latest job postings.

Shout out to our partner, Tech CXO Launchpad!

Shout out to our partners at ​Tech CxO LaunchPad​. Connect with ​Karen Bruno​ to learn more about the Program, the benefits, the outcomes, and how this Program provides a blueprint for new C-Level Execs or the path to the C-Suite for rising stars.

Now I want to hear from you, Reader

Do you feel optimistic or pessimistic about the job market right now?