Kelly Services has a diverse portfolio, covering professional and industrial staffing along with fast-growing education, science, engineering, and technology sectors. The company earns approximately $4.3 billion in annual revenue. Under Perry's leadership, the organization is advancing a modernization initiative that updates outdated systems and incorporates innovative solutions, all while staying true to its mission of making work accessible and fulfilling.

A CIO’s Strategy for Long-Term Tech Evolution

Perry oversees every aspect of global technology at Kelly. "If it plugs in and it's not working, it falls under IT," he quipped. However, his responsibilities extend far beyond that, centering on long-term modernization amid rapid technological change. “We’re striving to make decisions that will remain effective for the next decade,” he stated. “What was successful four years ago may not serve us well today.”

An important focus has been the integration of recently acquired companies. "Incorporating these acquisitions into the Kelly core reduces inefficiencies," Perry explained. "We're also reevaluating our applicant tracking, CRM, and ERP systems—tools that have been around for a while and now require updating."

Learning from Acquisitions and Building Stronger Foundations

The 2024 acquisition of Motion Recruitment highlights Perry's open-minded approach to innovation. He praised Motion for its progressive architecture, noting, “They had implemented Workday, connected it with Bullhorn, and integrated a CRM system. It was a fresh and contemporary tech stack.”

Rather than imposing top-down integration, Perry emphasized collaborative learning. “The ‘Kelly Core’ might need adjustments to accommodate superior technologies,” he observed. Although there were challenges in scaling a system initially designed for a smaller private equity-backed firm, he noted that “the Core is intact,” giving them an advantage in their transformation efforts.

Institutionalizing AI through Governance and Grace

AI plays a vital role in Kelly’s modernization strategy. Perry outlined the AI Council's three-part strategy: legal and compliance oversight, exploration of external opportunities, and evaluation of internal processes. “There was a major shift coming,” he said, “and the Council had already developed a model to assess and measure those opportunities.”

One significant outcome was Grace, an internally developed lightweight AI interface. “We support nearly 5,000 users with about $700 a month in AI expenses,” Perry revealed. Grace enables employees across the organization to experiment with AI without needing personal accounts, while also gathering data on popular applications. “For instance, resume formatting is a common task,” he added. “We embedded that function directly into Grace.”

The Power of Contextual AI and Emerging Opportunities

Perry is now leading an effort to embed AI contextually within Kelly’s SaaS tools. “Grace as a standalone site was a solid first step,” he remarked. “But we are now embedding it directly into the platforms people use daily, like Bullhorn or Workday.”

The objective is to eliminate inefficiencies—such as copying and pasting between systems—and provide assistance exactly when needed. “Shouldn’t AI function like a digital adoption platform? Always available and relevant?” Perry questioned. A prototype has already been demonstrated internally, aiming to offer intelligent, proactive support across various platforms.

Reflections from Amazon and a Product-Led IT Mindset

Before joining Kelly, Perry served as CIO of Robert Half International for thirteen years. Between that role and his current position, he took an unexpected detour as Senior Manager of Technical Program Management at Amazon. His time at Amazon left a lasting impact. Working on both Kindle and Halo—a health and fitness tracking service discontinued in 2023—he absorbed the customer-focused product development discipline Amazon is known for. “Amazon taught me to ask, ‘What problem am I solving for the customer?’ rather than ‘What feature should I build next?’” he reflected.

He has since applied this mindset to internal product development at Kelly, incorporating planning methods inspired by Amazon’s OP1 process. “We asked each team to write six-page documents outlining their achievements, challenges, and priorities,” he shared, referencing a well-known practice introduced by Jeff Bezos at Amazon. “It brought to light recurring issues and helped us align more efficiently.”

A Future Fueled by AI and Human Potential

Looking forward, Perry is enthusiastic about the swift progress of AI. “Capabilities that seemed out of reach six months ago are now attainable,” he said. Yet, he remains aware of the uneven understanding and success with AI across teams. “Some developers are building full-stack AI applications in hours, while others are still grappling with bugs introduced by AI-generated code.”

Ultimately, Perry is placing a strong bet on context-aware AI. “We're uncovering new use cases constantly—even in areas like internal audit,” he noted. “Now we have stronger justification for investment because we can observe real usage and value. Our challenge is how quickly we can move from prototype to production, given the immense potential to enhance our workforce.”

Peter High is President of Metis Strategy, a business and IT advisory firm. He is the author of three bestselling books, including his most recent, Getting to Nimble. He also hosts the Technovation podcast series and speaks globally. Follow him on Twitter @PeterAHigh.

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