AI Is Rewriting the Executive Hiring Playbook

Artificial intelligence is changing far more than how organizations build products. It is fundamentally reshaping what companies look for in leadership. Evan Berta, an associate at Hunt Scanlon Ventures, examines new insights from Insight Partners and explores why product and engineering executives are increasingly being evaluated on adaptability, commercial thinking, and organizational leadership rather than technical expertise alone.

Insight Partners’ latest research suggests the AI era is creating a new executive hiring playbook. Based on more than 400 executive searches and interviews with over 1,400 leadership candidates, the firm’s talent team argues that many of the characteristics defining today’s strongest product and engineering leaders would have been viewed as weaknesses only a few years ago.

Small teams. Incomplete roadmaps. Leaders willing to admit they do not yet have the answers. CTOs redesigning organizational structures rather than simply managing technology.

These are no longer warning signs. They are increasingly becoming indicators of organizations that are adapting successfully to AI-driven transformation.

Technical Expertise Is No Longer Enough

For years, product and engineering leaders were largely evaluated on technical depth, execution, and delivery. AI is changing that equation.

“The conversation has shifted from whether leaders understand technology to whether they can reshape organizations around it.”

As engineering productivity accelerates and software development becomes increasingly automated, the bottleneck is shifting away from building products and toward commercializing them. Pricing strategy, customer adoption, organizational design, and cross-functional execution are becoming equally important leadership responsibilities.

“The conversation has shifted from whether leaders understand technology to whether they can reshape organizations around it,” said Evan Berta, an associate at Hunt Scanlon Ventures. “Technical credibility still matters, but increasingly it is the ability to lead change, make decisions under uncertainty, and connect technology to business outcomes that separates exceptional leaders.”

This evolution is changing how boards, CEOs, and investors evaluate executive talent.

Curiosity Becomes the Competitive Advantage

Among the six leadership characteristics identified by Insight Partners, one stands above the rest: intellectual curiosity. The report argues that curiosity is no longer a desirable personality trait. It has become a leadership requirement.

Rather than simply sponsoring AI initiatives, leading executives are expected to experiment with the technology themselves, continually test new tools, and develop firsthand understanding of how AI changes workflows and decision-making.

“Organizations can teach new skills, but curiosity is much harder to develop,” said Mr. Berta. “The leaders moving fastest today are personally experimenting with AI, questioning established assumptions, and encouraging their teams to do the same.”

That willingness to learn increasingly distinguishes leaders who are adapting from those who are simply managing legacy operating models.

The New Leadership Skills

Insight Partners also identifies a broader shift in the capabilities organizations now prioritize.

Commercial instinct has become increasingly valuable as companies focus on monetization rather than simply product development. Comfort with ambiguity is replacing certainty, as executives make decisions before complete information exists. At the same time, change management has become a core leadership competency as organizations continually redesign workflows, teams, and operating models.

Operational discipline remains essential, but it now exists alongside experimentation. “The strongest leaders are balancing speed with structure,” claims Mr. Berta. “They are creating environments where teams can experiment rapidly without sacrificing execution or accountability.”

That balance may become one of the defining characteristics of leadership in the AI era.

Executive Search Is Changing Too

These evolving leadership expectations are also reshaping executive search.

According to Insight Partners, executive searches are taking longer as organizations struggle to identify leaders with the combination of technical understanding, commercial perspective, and organizational leadership increasingly required by AI transformation. At the same time, AI-ready executives are commanding compensation premiums of 10 to 15 percent.

The implications extend beyond engineering.

“Executive search is becoming much more about evaluating learning agility and leadership mindset than simply matching experience to a job description.”

As AI reshapes virtually every business function, many of the qualities identified in product leadership are becoming increasingly relevant across finance, operations, marketing, HR, and the broader C-suite. Organizations are searching less for functional specialists and more for adaptable enterprise leaders.

“Executive search is becoming much more about evaluating learning agility and leadership mindset than simply matching experience to a job description,” said Mr. Berta. “Past success still matters, but future potential is increasingly determined by how quickly leaders can adapt.”

The Shift Ahead

Insight Partners’ findings reinforce a broader shift taking place across executive leadership.

AI is changing how organizations operate, but it is also changing how leadership itself is evaluated. Technical expertise remains important, yet it is no longer sufficient on its own. Organizations increasingly need executives who can navigate ambiguity, redesign teams, accelerate adoption, and translate technological capability into commercial performance.

For executive search firms, this changes both candidate evaluation and client advisory. For boards and CEOs, it changes what great leadership looks like.

The leaders most prepared for the AI era may not be those with the deepest technical expertise. They may be the ones most willing to continuously rethink how organizations learn, adapt, and create value.