The Heller Team’s Career Advice for Technology Executives

What does it take to land your next technology leadership role? The Heller team shares hard-won insights from thousands of executive placements: how to work with recruiters, ace your interviews, navigate private equity, and leverage AI in your search.

Every day, the team at Heller reviews resumes, preps candidates for interviews, and advises seasoned and emerging technology leaders on their careers. As CEO of our technology executive search firm, I often hear the team’s pearls of advice, and I learn something new every time.

To guide you, our devoted readership, in managing your career, we’ve compiled our senior team’s best job search recommendations in this value-pack of advice. Enjoy! 

How to work with executive recruiters

Tim Hobson, senior principal at Heller, encourages executives to build a network of executive recruiters, whether you are currently on the market or not.

As an executive, your next role is more likely to come from a retained recruiter than a LinkedIn posting or company career page. Build as many long-term relationships with search professionals as possible. When a friend gets a new job, ask for an introduction to the recruiter. Even if you don’t want a role a recruiter has on offer, take the general introduction meeting. Refer rock stars from your network for roles that are not right for you and drop us a line every six weeks or so. All this activity will keep you top of mind so that when we are retained on a search that is right for you, we know the first call to make.

Be transparent with your recruiter and professional in your interviews

Kerri Westberg, senior principal, has led seasoned leaders and up-and-comers through successful interview gauntlets.  As interviews have become virtual, she has seen a shift in candidate behaviors and advises candidates to make professionalism (and transparency) a priority.

When candidates haven’t interviewed in a long time, they can forget basic interview etiquette, especially in our age of virtual interviews. Remember to treat these interviews formally. Wear an appropriate shirt, take the call from a laptop, not your phone, and have a quiet space to talk with minimal background distractions. Don’t take the call from your car! If travel prevents you from finding a quiet space, tell your recruiter, so we can work through logistics with you.

On that note, leverage our expertise throughout your interview and compensation negotiation process. From your first interaction with us, be candid about your compensation or location requirements, so there are no surprises at the offer stage. The more transparent you are with us, the more we can advocate for you.

Tune out the headlines noise

Managing Director, Jason Henninger, has spent the last 12 months doubling down on his high-demand networks of growth CISOs. Jason can attest that from security to operations to innovation, tech leadership hiring will be a dynamic market.

Don't be swayed by the constant headlines about technology layoffs, cost-cutting, and AI replacing tech roles. If you're a technology leader who can drive results, you'll remain employable for the foreseeable future.

During economic downturns, CEOs hire new CIOs to reduce costs. During growth periods, technology leads innovation. And right now, AI is driving every CEO to approve more systems and data integration—both critical components of an AI operating model.

Markets will always fluctuate, and the demand for big tech leadership roles will ebb and flow. But a clear, strategic job search will always matter more than current market conditions.

Treat your job search like a sales campaign

Charley Betzig, managing director, has spent his career in executive search and has guided many CIOs, CTOs, and CISOs through their job search and interview process. His “treat your job search like a sales campaign” advice is market-tested.

Think of your job search as a full-time sales position, with you as the product. First is process: Set yourself daily goals and track your outreaches; these small activities will stack up into big results, and achieving something daily is good for mental health!

Second, is sales strategy. Don’t just apply for a role on LinkedIn. Research the hiring manager to find a common connection, then ask for an introduction. Pick your target companies, review their senior management team, and turn cold leads into warm ones.

Third, leverage your network. Reach out to business partners, bosses, vendors, and colleagues to let them know what you are looking for, which should be both broad and specific. (“CTO position in healthcare” rather than “something challenging”.) Once a quarter, send this group an update on your search. Your goal is to create a swell of network activity to give you exposure to target roles.

Avoid a jumpy resume (by making “culture” an attention point)

In focusing both on her executive placements and their long-term success, Client Partner Brittany Danehy knows that a “jumpy” resume can be a turn-off to prospective employers. She advises candidates to think hard about cultural fit, which is often the force behind a short engagement.

One of the biggest challenges for recruiters is helping candidates explain frequent moves, one year here, two years there, even when each change had a perfectly reasonable cause. Not every role will be a long-term fit, and that’s okay, but it’s important to understand why a job wasn’t the right match, so you don’t repeat the same pattern.

Take time to reflect on what you truly need to do your best work: leadership style, culture, team structure, pace, expectations, and support. And remember, you should be interviewing your employer just as much as they’re interviewing you. Ask questions that help you understand whether the environment is one where you can realistically succeed. Thinking proactively about long-term fit not only leads to better career decisions. It also helps you build a clearer, more cohesive story as you progress through the interviews.

Tell (and rehearse) a consistent and compelling story

As all of us at Heller can attest, storytelling has become a differentiating skill in technology leadership, including in your job search. Zach Peikon, managing director, emphasizes that storytelling should happen at multiple levels of your search.

Your resume should tell your impact story. Focus on the critical areas of the role you’re applying for and demonstrate how you’ve added relevant value to your organizations. Then, practice until you can confidently articulate what you did, how you did it, and the result. If you can tell that story clearly, you’ll be ahead of the pack. The more you rehearse, the more comfortable – and successful – you’ll be on an interview. Your digital presence tells a story too, so update your LinkedIn headline with recent achievements. And remember, we’re only in the second inning of AI adoption. All technology leaders need to weave AI into their story—how they’re integrating AI into their toolkit to drive business forward.

Balance high-level strategy with the details of the work

Principal Gianna Kane provides valuable advice about one of the toughest interview challenges for technology leaders – how to present yourself as strategic and detailed all at once.

As a technology leader, every project from roadmap to execution requires significant time, strategy, and overcoming tremendous hurdles. There is a lot to discuss! When describing your experience driving transformation, learn to balance high-level insights with detailed specifics. In interviews, keep your answers concise and at the strategy level, adding technical depth only when appropriate or requested. The level of detail should align with your audience. HR interviews focus on culture, leadership, and organizational challenges, so keep technical accomplishments in your back pocket. When you talk to technology leaders, bring in more detail around tools, vendors, and technologies—and how hands-on you were. The goal: balance strategy and detail, tailored for each interview.

It’s your interview process. Manage it.

Carol Lynn Thistle is director of client delivery and founded Heller with me some 16 years ago. She is one of the most well-connected, impactful, and knowledgeable CIO recruiters in the industry. Carol Lynn knows that you, as a candidate, have agency throughout the interview process, but you need to know when and how to use your advantage.

Your leadership skills should apply to your job search, too.  If your recruiter doesn’t offer interview prep—ask for it.  Suggest they walk you through each interviewer, their business goals and IT pain points. A prep call gives you and the recruiter a chance to review the role’s requirements, align on what to emphasize, and make sure you’re highlighting the strengths that matter most for that specific interview.

When you’re in the interview, use your communication skills to shift the dynamic. At the right moment, answer the question, but follow it with a thoughtful question of your own. That back-and-forth creates a natural dialogue and helps you build a genuine connection with the interviewer.

Being ready to share a meaningful lesson you’ve learned from a “failure” can really work in your favor. Hiring managers value honesty, which often opens the door to a more engaging, human conversation rather than a rigid Q&A. You show self-awareness, growth, and the ability to reflect—qualities that stand out and, ultimately, qualities that get you hired.

Remember, Private Equity is different

More than half of our search work at Heller is with private equity-backed businesses, and Kelly Doyle, managing director, leads much of it. Her career advice applies both to technology leaders in PE and to public company executives interested in “going private.”

PE deal makers and their portco CEOs have one thing in mind when reviewing your resume: fast growth.  Everyone who interviews you will be aligned around their value creation plan, and they want to know that you can be a catalyst for the VCP, not a drag.  On your resume, emphasize team growth, M&A growth, EBIDTA growth, and include timelines. While every technology leader should be fluent in finance, for PE it is non-negotiable. So, make sure you know your numbers when you interview.

Remember that the PE community is incredibly well networked; they will want to know the PE firms behind your employers, and they will not hesitate to give one of those partners a call. Keep those PE relationships fresh, because the network in PE is very productive. 

Use AI as a job search and resume-building tool.

Carrie Kovach, client partner, is an innovator in technology adoption, and advocates leveraging the emerging AI toolset in your search.

Use ChatGPT or Copilot to sharpen your resume. Input your target role and key accomplishments, and AI will reframe bullet points for impact and suggest stronger action verbs. For interview prep, ask AI to generate common questions for your role and help you craft thoughtful questions based on the company’s recent initiatives.

AI also accelerates networking. Use it to draft personalized LinkedIn outreach—professional but warm, clear about your intent. These tools can help you phrase messages to your network about your job search and offer to share an updated resume. The key is using AI to enhance your voice, not replace it.

Your Linked In profile is not enough; be active

Pam Kurko, managing principal, has been advising candidates at Heller for more than a decade. Pam focuses on your LinkedIn activity, which has become table-stakes in a job search.

In our Recruiter version of LinkedIn, the algorithm prioritizes candidates who are active on the platform. A search for “CIO healthcare,” surfaces the most engaged profiles first—your activity directly impacts your visibility.

For job seekers, this means consistent engagement is key. Post industry insights, share relevant content, or comment thoughtfully on others’ posts. Small, daily interactions signal to the algorithm that you’re an active professional worth surfacing in searches.

Creating a LinkedIn profile is not enough. Update your headline with recent achievements, refresh your summary to reflect current goals, and add new skills and certifications as you acquire them. A static profile, no matter how impressive, won’t rank as high as one that shows ongoing professional growth.

Use your value proposition to define your search

And finally, my challenge to you for 2026: imagine you wave a magic wand and get one hour with any CEO in the market to explain why you, specifically, are the best person to guide them through what can only be an eventful next three years.

Personally, I would love to use my magic hour to explain to Lin-Manuel Miranda why I should be the subject and star of his next Broadway hit. But I would be foolish to waste that hour on Lin-Manuel, because my chances are so very slim.  But convincing a new CEO that my firm can deliver first-rate tech leadership talent? I’ll take the meeting!

My point is this: if you can identify even three CEOs who need you to transform, that's the beginning of your strategic job search.  If you’ve never been in banking, a banking CEO will likely not see your value. If you’ve transformed manufacturing operations, your CEO target list should come easily into view.

This is your job search story: What CEOs need you? Turn that list from one to 20 and network your way to it. And then use my team’s pearls of wisdom to turn your target list into your story’s next chapter.