Inside Kelly Services Tech And AI Journey With CIO Sean Perry

Sean Perry, Chief Information Officer of Kelly Services, oversees global technology for a company dedicated to connecting job seekers with opportunities across multiple sectors. “We help people on a daily basis find meaningful work,” Perry shared. “To be able to leverage technology to deliver that is something that has been a great enjoyment throughout my career.”

Kelly Services has a diversified portfolio, including professional and industrial staffing as well as fast-growing education, science, engineering and technology sectors. The company generates approximately $4.3 billion in annual revenue. Under Perry’s leadership, the company is driving forward with a modernization initiative that updates legacy systems and integrates cutting-edge solutions, all while preserving the company’s mission of making work accessible and fulfilling.

A CIO’s Strategy for Long-Term Tech Evolution

Perry’s purview encompasses every aspect of global technology at Kelly. “If it plugs in and it’s not working, it’s IT,” he joked. But his responsibilities go much deeper, focusing on long-term modernization during a time of rapid technological transformation. “We’re trying to make good decisions that’ll last 10 years,” he explained. “What worked four years ago isn’t necessarily going to help us today.”

A core focus has been integrating recently acquired companies. “Engaging those acquisitions and bringing them onto the Kelly core eliminates friction,” Perry said. “We’re also rethinking our applicant tracking, CRM and ERP systems, tools that have existed for a long time and now need modernization.”

Learning from Acquisitions and Building Stronger Foundations

Kelly’s acquisition of Motion Recruitment in April 2024 exemplifies the CIO’s open approach to innovation. Perry praised Motion for its forward-thinking architecture when he said, “They had implemented Workday, connected it to Bullhorn and added a CRM. It was a fresh, modern tech stack.”

Rather than enforcing top-down integration, Perry emphasized mutual learning. “The ‘Kelly Core’ might need to change to accommodate this more capable technology,” he noted. He acknowledged challenges in scaling a system designed for a smaller private equity-backed company but noted that “the Core is all there,” providing a leg up in their transformation journey.

Institutionalizing AI through Governance and Grace

AI has become a key enabler of Kelly’s modernization. Perry described the AI Council’s three-pronged approach: legal and compliance, external opportunity scouting and internal process evaluation. “You had this sea of change coming in,” he said, “and the Council had already built a model for how to assess and measure opportunities.”

One of the most impactful outputs was Grace, a lightweight AI interface built internally. “We support close to 5,000 users on about $700 a month of AI spend,” Perry revealed. Grace allows employees across the organization to experiment with AI without needing individual accounts. It also collects data to surface popular use cases. “For example, reformatting a resume is a common task,” he offered. “We built that functionality directly into Grace.”

The Power of Contextual AI and Emerging Opportunities

Perry is now spearheading an initiative to embed AI contextually into SaaS applications used by Kelly. “Grace as a separate website was a good first step,” he said. “But now we’re working on embedding it in the actual tools people use, like Bullhorn or Workday.”

The goal is to eliminate friction—copying and pasting between systems—and to deliver assistance at the moment it’s needed. “Shouldn’t AI work like a digital adoption platform? Always available and in context?” Perry asked. The prototype, already demonstrated internally, is aimed at providing proactive, intelligent support across platforms.

Reflections from Amazon and a Product-Led IT Mindset

Perry had prior CIO experience, spending 13 years as the CIO of Robert Half International. In between that experience and his current role, however, he spent took an unusual turn as Senior Manager of Technical Program Management at Amazon. Perry’s time at Amazon left a lasting impression. Working on both Kindle and Halo, a health and fitness tracking service and devices that was discontinued in 2023, he learned the discipline of customer-centric product development that company is famous for. “Amazon taught me to step back and ask, ‘What’s the customer problem I’m trying to solve?’ rather than ‘What feature should I build next?’

He has since brought that philosophy to internal product development at Kelly, introducing planning processes inspired by Amazon’s OP1 methodology. “We had each team write six-page documents about their wins, challenges and priorities,” he said, highlighting another famous practice that Jeff Bezos introduced at Amazon years ago. “It surfaced common pain points and helped us align more effectively.”

A Future Fueled by AI and Human Potential

Looking ahead, Perry is excited about the rapid evolution of AI. “Capabilities that seemed impossible six months ago are now within reach,” he said. But he’s mindful of the uneven distribution of understanding and success with AI. “Some developers are building full-stack solutions with AI in hours while others are still struggling to fix bugs introduced by AI-generated code.”

Ultimately, Perry is betting big on context-aware AI. “We’re discovering use cases everywhere, even in internal audit,” he noted. “Now we have more justification to invest because we can see real usage and value. Our challenge is how quickly we can move from prototype to production because the potential to empower our workforce is enormous.”

Peter High is President of Metis Strategy, a business and IT advisory firm. He has written three bestselling books, including his latest Getting to Nimble. He also moderates the Technovation podcast series and speaks at conferences around the world. Follow him on Twitter @PeterAHigh.