SHRM's 2025 benchmarking data puts the average cost-per-hire at $49,800 CAD for executive roles, nearly seven times the cost of a non-executive hire.
Hiring technology executives adds another layer of complexity: the relentless pace of change. What a CTO or CIO is expected to deliver constantly shifts, making it difficult to pin down what success actually looks like in a job description.
This article explores some common mistakes companies make when hiring tech executives and how to avoid them.
Why Is it Hard to Hire a Tech Executive?
Hiring a tech executive can be challenging because the jobs keep changing shape. Deloitte's Tech Exec Survey found that 80% of tech leaders say their roles have significantly expanded to meet business objectives, often well beyond the scope of their original job description.
“The market is extremely competitive right now," says Sean Casey, Partner, at Pender & Howe. “But the one constant is that the landscape changes so quickly that organizations take comfort in hiring someone who's already 'been there, done that.' The problem is, what the landscape looked like a year ago has already changed significantly."
The rapid adoption of AI is only accelerating that shift. The same Deloitte research found:
- 45% of tech leaders say GenAI skills are now the most urgently needed competency in their organization
- Nearly 7 in 10 plan to expand their technology team specifically to close that GenAI skills gap.
This pressure is not limited to companies at the forefront of AI adoption. Salesforce's global CIO research found that 94% of CIOs say scaling AI is forcing them to expand their own skill sets, regardless of industry.
Relying on past comfort over future requirements is where executive searches begin to break down. When hiring teams fall into that trap, it typically shows up in three critical missteps:
Mistake #1: Hiring for a Title Instead of a Mandate
"We need a CTO" isn't a hiring strategy. It is a placeholder for a decision the leadership team has not made yet. Two companies might both post a job for a "CTO," but need them to achieve entirely different objectives, including:
- Building (or rebuilding) an engineering team
- Modernizing infrastructure or cutting infrastructure costs
- Launching a new product
- Leading an AI initiative across existing business units
Some of these scenarios often require different backgrounds, personalities, and interview processes. Yet companies routinely post a generic job description and hope the right candidate emerges.
“AI has flipped the script on how data is consumed, moving from traditional dashboards to LLMs and predictive models that put information directly in the hands of the business, not just the technology team,” Casey says. “That means you need leaders who bring multiple skill sets and can operate across functions. When you're hiring strictly for a title, you limit your ability to hire for the mandate the organization actually needs."
To avoid this, he suggests:
- Get the CEO, the board, and key stakeholders to agree on specific targets before the executive search starts. “Start with the problem you're actually trying to solve,” Casey says, explaining that without that alignment, each stakeholder walks into candidate interviews evaluating against a different, unspoken version of the role.
- Write the job description around those targets, not phrases like "lead tech strategy," which is vague language and can mean something different to everyone reading it. A specific target like "cut infrastructure costs 30% while scaling to 10x transaction volume" gives everyone the same yardstick and does real filtering: candidates who can't picture delivering on it self-select out early.
- Screen for whether candidates have hit those objectives, not whether they've held the title. A “VP of Engineering” title means something different at a 20-person startup than at a 2,000-person company. A track record against the actual outcome, and at what scale, predicts performance in a way a title alone doesn't.
Mistake #2: Not Defining the Role as Strategic or Operational
Even once the mandate is clear, there's a second question many companies don't ask: is this person running the technology team or growing the business through it? The answer usually comes down to how the company sees technology internally.
Deloitte found a near-even split in how senior tech leaders say their own organizations view technology:
- 52% view it as a primary driver of revenue and growth
- 48% view it as a support function for operations, security, and cost control
Neither is wrong, but failing to choose between them creates an identity crisis for the search. A CIO tasked with driving e-commerce revenue often needs a different leadership profile than one hired to stabilize core systems and costs.
The first step, Casey says, is deciding whether your mandate is to stabilize operations, transform systems, or unlock new revenue. Once you’ve figured that out at an organizational level, you can then build your search around that priority.
Partner, Pender & Howe
„We've seen a consistent pattern over the last 12 months, especially with mid-market and scaling technology companies. Many are asking for a candidate who blends strategic and tactical strength, someone who can help roadmap the next stage of growth while still staying close enough to the day-to-day to get their hands dirty. To find that right leader, though, you really have to understand that in advance.“
Sean Casey
Mistake #3: Hiring for Today's Tech Environment Instead of What's Next
According to an analysis of recent research, failure rates for senior leaders typically fall between 30% and 67%, with failure defined as falling short of performance expectations, struggling to transition into the role, and general disappointment within the first two years.
Much of that failure traces back to the hiring process itself, and specifically to testing for the wrong thing: whether a candidate has succeeded in an environment like the one the company has today, rather than whether they can lead through the one it's about to become. For example:
- A CIO who kept systems stable for years may never have led a major overhaul
- A CTO with strong product experience may have no track record of rolling out AI systems company-wide
Both look like strong hires for a job description written around current-state experience. Neither may be prepared for what the company is actually asking them to do next.
What companies should do instead:
- Identify specific examples of leading through comparable shifts (a platform migration, an AI rollout, a security overhaul), not just tenure in a similar-looking role
- Don't treat a long, stable track record as either proof of readiness or a strike against a candidate. Weigh it as neutral, and look for direct evidence of the specific capability you need
How Do You Reduce the Risk of a Failed Tech Executive Hire?
All three mistakes come from the same root cause: a lack of internal alignment about what the tech executive is actually being hired to accomplish. The title gets decided before the mandate does, and the search runs on assumptions nobody said out loud.
Before opening a search, get alignment on three things:
- What this executive needs to accomplish in year one, stated as an outcome, not a duty
- Whether the mandate is closer to running the technology team as-is, overhauling how it operates, or using it to grow revenue
- Whether candidates have led through change comparable to what's ahead, not just managed an environment similar to what you have today
Once those decisions are made, the title becomes a starting point instead of the definition of the role.
Work With Pender & Howe on Your Next Technology Search
With offices across Toronto, Montreal, Vancouver, Calgary, Edmonton, Boston, and New York, Pender & Howe combines boutique-level partner involvement with deep sector intelligence across technology, life sciences, industrial, consumer goods, and professional services.
Whether you're building out a technology leadership team, running a confidential CTO or CIO search, or replacing a leader who wasn't the right fit, we bring the agility of a smaller firm together with deep sector knowledge and a data-driven approach. Every recruitment is a true partnership, grounded in integrity, curiosity, and genuine care.