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How AI is Rewriting the CIO and CTO Playbook

How AI is Rewriting the CIO and CTO Playbook

By Retained | January 20, 2026

As we enter 2026, one thing is clear: Artificial Intelligence isn’t just transforming technology, it’s redefining leadership. For organizations seeking top-tier executives, understanding this shift is critical. AI in executive leadership is now critical for organizations seeking top-tier talent and strategic advantage The roles of CIOs and CTOs are evolving faster than ever, and AI is at the center of that change.

Why It Matters

Traditionally, CIOs focused on IT operations and infrastructure, while CTOs drove innovation and technology strategy. Today, AI is blurring those lines. Automation is reducing routine IT tasks, freeing CIOs to become strategic business enablers. Meanwhile, CTOs are expected to lead AI architecture, model deployment, and cross-functional tech partnerships. Success now requires a blend of business acumen, AI literacy, and leadership vision.

What’s Changing

Prakash Muthukrishnan emphasizes that modern CIOs and CTOs must go beyond technology, they must become cultural champions of AI.

CIOs and CTOs should become cheerleaders of AI democratization in their organization. They should enable business users to develop their own solutions to improve productivity by establishing proper security fences and data protection guard rails.

This mindset marks a shift from control to enablement, unlocking productivity while maintaining trust, compliance, and security. It also requires new ways of working: HR and legal teams must be part of every major initiative, ensuring workforce impact, ethics, and governance are considered from day one.

AI also changes how success is measured. Prakash urges leaders to think about products, not implementations. AI enables faster development of offerings, shorter time-to-market, and competitive advantage, but only when leaders focus on outcomes rather than pilots.

Finally, AI transformation demands clear ownership. CIOs and CTOs must define a North Star for their AI journey, secure buy-in from the C-suite and board, and adopt iterative build–test–deploy–learn loops that allow the organization to adapt quickly while staying aligned to long-term strategy.

Implications for Executive Search

At Retained, we’re helping clients navigate this evolution by:

  • Defining Modern Roles: What does a CIO or CTO look like in an AI-first enterprise?
  • Leveraging AI in Search: Using advanced tools for candidate matching and leadership assessment.
  • Providing Market Intelligence: Salary benchmarks, talent availability, and competitive positioning.

Your Next Move

AI is no longer optional; it’s a leadership imperative. For organizations planning growth, transformation, or succession, now is the time to rethink the executive team. Leaders who embrace AI responsibly, strategically, and culturally won’t just implement technology, they will shape the future of their enterprise.

Meet The Newest Team Members of Retained

By Retained | January 15, 2026

Retained is proud to announce the addition of three team members to our growing team. As we continue to expand our executive search capabilities and deepen our client partnerships, these new hires bring a wealth of experience, leadership, and strategic insight that aligns seamlessly with our mission to deliver tailored, client-centric executive search solutions.

 

Patti Dismukes Joins Retained as Senior Advisor

Patti Dismukes career reflects a strong track record of leading large-scale transformational initiatives and optimizing financial management processes. She has held leadership roles at several regional, national, and global companies, where she launched new service offerings, maximized resources to meet client goals, and led enterprise-wide initiatives focused on evolving business models to adapt to changing market conditions and disruptive forces.

Patti’s dedication to improving the lives of young women and girls has guided her involvement with organizations such as Women in Technology (WIT), TechBridge, and Year Up. She served six years on the WIT Board, including as Board President from 2020 to 2023, where she led organizational changes and supported the creation of innovative programs, including the WIT Single Mothers Program, Board Readiness, and WIT Career ConneXions. From 2023 to 2025, she also served on the Board of Advisors for 3Ci, helping expand their service offerings.

In recognition of her contributions, Patti received the Ann Cramer Volunteer Award and the TAG Sales Leadership Community Award in 2019.

Beginning in 2026, Patti will serve as Senior Advisor to Retained, supporting the firm’s mission to provide strategic, tailored, and client-centric executive search solutions. In this role, she will leverage her experience to assist with strategic growth plans, implement best practices, and lead executive search opportunities

 

Anthony Angelo Joins Retained as Director of Business Development

Anthony Angelo brings over 15 years of experience in business staffing solutions to his role as Director of Business Development at Retained. Known for his consultative approach and commitment to building lasting partnerships, Anthony works closely with executive leadership to deliver high-impact executive search strategies tailored to each organization’s unique needs.

Throughout his career, Anthony has supported companies of all sizes, from nimble startups to Fortune 500 enterprises, across industries like healthcare and IT. His track record of success in highly complex, fast-moving environments is rooted in his deep understanding of compliance, precision, and speed. Whether navigating nuanced talent challenges or scaling leadership teams, Anthony approaches every engagement with a thoughtful, white-glove touch.

A three-time Presidents Club honoree (2017–2020) and part of a team recognized with a Best of Staffing award in 2022, Anthony is no stranger to delivering excellence. He was drawn to Retained by its culture of commitment, to clients, to candidates, and to each other, and is energized by the firm’s long-term, partnership-first approach to executive staffing.

Outside of work, you’ll find Anthony cheering on the Atlanta Braves, relaxing in Aruba, or spending time with his family and his dog. His superpower? Empathy, a trait that serves him well in both business and life.

 

Melisa Huskic Joins Retained as Marketing Associate

Melisa Huskic serves as a part-time Marketing Associate at Retained, bringing creativity, curiosity, and a strong desire to learn to the marketing team. She supports the execution of digital marketing initiatives across platforms including LinkedIn, YouTube, email, and the website, working closely with the Marketing Communications Manager on content development, campaign support, and site updates.

Prior to joining Retained, Melisa contributed to the Marketing Committee at Georgia Gwinnett College’s Kaufman Library, where she supported efforts to strengthen brand awareness through data-informed outreach, strategic messaging, and engaging social content. Known for her thoughtful and adaptable approach, Melisa helps keep Retained’s marketing efforts both organized, and audience focused.

 

Looking Ahead

With the addition of Patti, Anthony, and Melisa, Retained continues to build a strong team rooted in expertise, collaboration, and a shared commitment to client success. Retained’s new team members further our mission to empower companies to thrive by connecting them with exceptional, diverse executive talent, and reinforce our commitment to putting people first in every search.

2025 Retained Rewind: A Year in Review

By Retained | December 17, 2025

One of the most rewarding aspects of my career has been the opportunity to lead in ways that positively impact people and communities. While my roles have spanned park districts, the YMCA, health charities, tech associations, coaching companies, and staffing firms, a consistent playbook has guided my work: listen closely to customers and prospects, attract and develop exceptional talent and partners, build a strong brand, and consistently exceed expectations in delivery.

Retained. has been no exception.

In January, Retained entered its second year as a core division of Tier4 Group. Under the leadership of Betsy Robinson, Tier4 Group has become a powerhouse in delivering high-quality recruiting services, reflected in a remarkable 96 Net Promoter Score. While the team had already completed several executive leadership placements, Retained was, in many respects, still a startup throughout 2024.

Last year we laid the foundation and activated the playbook. Anyone who has launched a company or built a new division understands that success begins with a strong product, but brand awareness is just as critical. While Retained offered a differentiated and high-quality executive search solution, it was not yet widely known or fully understood in the marketplace. Many organizations already rely on long-standing search partners or internal recruiting teams, making market entry less about relationships and more about earning trust and share.

Throughout 2024, our focus was on building the brand, assembling the right team, and developing the infrastructure to scale. We successfully completed several searches that validated our approach and positioned us for meaningful growth. As a result, we entered 2025 primed for expansion. We exceeded our goals, growing closed searches by more than 300%. Still, like most leaders, we’re not satisfied.

Looking forward to 2026, we’re ready to scale even further. In order to support our ambitious growth, we’ve expanded our marketing capabilities and are adding a Business Development Director to our growing team. We see even greater opportunity ahead, and we’re just getting started.

If you’re planning an executive search in the year ahead, let’s talk. Retained brings deep expertise, a commitment to inclusive hiring, and a relentless focus on results. Backed by an award-winning recruiting team that knows how to deliver, you can be confident that we’ll find the right fit, the first time.

Thank you for your continued support!

CIO Corner | Featuring Yogaraj (Yogs) Jayaprakasam, CIO At Deluxe

By Retained | June 5, 2025

Fueling Innovation Through Curiosity, Architecture, and Outcomes. In this month’s edition of The CIO Corner, Tino Mantella is proud to feature Yogaraj (“Yogs”) Jayaprakasam, Chief Information Officer at Deluxe, a trusted payments and business technology company with more than a century of impact. Yoga is no stranger to transformation. With a calm, strategic demeanor and a sharp eye on what’s next, he’s helping Deluxe harness the full power of technology to serve its customers better and future-proof its operations. 

At the core of his leadership philosophy is a simple yet powerful idea: 

“Technology people must have an appetite to learn new tech, solution architecture, and be outcome-focused on their solutions.” 

This is more than a hiring preference, it’s a blueprint for building modern, agile IT organizations. 

 

Curiosity as a Catalyst

When Yogs evaluates potential team members, he’s not just scanning for resumes stacked with buzzwords or certifications, he’s looking for a hunger to learn. In a world where technological change is constant, he sees curiosity as a non-negotiable. 

This emphasis on intellectual curiosity reflects a shift in what defines high-performance in IT. It’s no longer just about what you know, but how fast you can adopt and apply.

 

The Architecture Mindset

The second trait Yogs highlights, solution architecture, might sound technical, but for him, it’s about much more than designing systems. It’s about thinking holistically, asking the right questions, and connecting the dots between technology, people, and purpose. 

Architecture is where innovation becomes tangible and where ideas start to take shape. People who understand architecture aren’t just coders, they’re builders, planners, and translators between business needs and engineering realities.

By embedding architectural thinking into all levels of his team, not just senior engineers, Yogs promotes scalable, sustainable tech development that avoids short-term fixes and leans into long-term vision. 

 

Outcome Over Output 

It’s easy for technology teams to fall into the trap of delivering features for the sake of velocity. But Yogs sets a different tone: one of intentionality and impact. 

His outcome-first mentality transforms how his team defines success. It also drives a greater sense of ownership, encouraging developers, architects, and analysts alike to stay close to the “why” behind their work. 

What makes Yogs stand out is not just his technical expertise or business insight; it’s his clarity of purpose. He’s building teams that don’t just execute tasks, but reimagine solutions.  Teams that don’t settle for “how things are,” but ask “how things could be.”

By centering hiring and development on curiosity, architecture, and outcomes, Yogs is future-proofing more than just technology; he is cultivating a culture of innovation from the ground up.

What a Midnight Noise Complaint Taught Me About Conflict Management

By Retained | June 4, 2025

Early in my career, I worked at the New Haven YMCA, and we were one of the largest providers of occupancy housing to those in need of a place to stay. It was a unique environment that taught me a lot, often in unexpected ways.

One night around midnight, I got a call from one of the residents. He said, “Mr. Mantella, can you please help me? It’s very late, and the guy next door is playing his radio too loud.” It wasn’t exactly an emergency, and I wasn’t thrilled to be disturbed at such a late hour, but once I settled down, I proceeded to handle the situation.

Over the phone, I instructed the resident to walk over, politely knock on the neighbor’s door, and ask them to turn the volume down since it was midnight. Thankfully, he did—and that was the end of it. But the moment stuck with me.

Since then, I’ve had countless situations where someone has come into my office and said, “Tino, can you help me? So-and-so is causing an issue.” In the past, I’d often step in right away—“Let me talk to them,” or “Let’s all meet together to fix it.” My instinct was to mediate.

But over the years, I’ve learned a better way.

Now, instead of immediately stepping in, I ask: “Have you spoken with them directly?” More often than not, the answer is no. What people want is to be heard, validated, and—if possible—rescued from discomfort. But growth happens in the discomfort.

I’ve come to believe that one of the best things leaders can do is empower others to handle conflict themselves. That doesn’t mean abandoning people or ignoring issues—it means coaching them, equipping them with the right approach, and then encouraging them to take the lead.

Here are a few takeaways I’ve learned about conflict management:

  • Start with empathy. Everyone’s experience is valid, even if the issue seems small to you.
  • Encourage direct communication. Avoid becoming the go-between whenever possible. Instead, help others feel confident in addressing the issue themselves.
  • Coach, don’t fix. Offer guidance and support, but allow others the opportunity to grow by handling the conversation.
  • Pick your moments to intervene. Sometimes, it is necessary to mediate—but it shouldn’t be the default.

That midnight noise complaint may have seemed small, but it taught me a big lesson: not every conflict needs to be solved for someone. Sometimes, the most powerful leadership move is to stand beside them, not in front of them, as they work through it themselves.

The Future Skills Every CIO Will Need, Part 2

By Retained | November 22, 2024

Key Takeaways from this article: 

  • Effective people management goes beyond traditional team leadership; it requires emotional intelligence (EQ), empathy, and building strong relationships across the organization.
  • CIOs will continuously push the boundaries of what’s possible, encouraging their teams to think outside the box and explore new ideas.
  • A data-driven mindset is essential for success in the role of CIO. 
  • By optimizing the user experience and adopting a customer-first mindset, CIOs can help their organizations stay ahead of customer expectations, driving greater engagement and long-term success. 

 

In our last article, we looked at three crucial skills, business acumen, effective communication, and cybersecurity, as future skills that every CIO will need to lead their organization into the future. In part two, we will explore four more skills that will define the next generation of tech leaders. These are skills that any leader should be looking for in their next CIO – let’s dive in. 

People Management and Emotional Intelligence 

In an era of vital collaboration and cross-functional teams, managing and leading people is a fundamental skill for any CIO. Effective people management goes beyond traditional team leadership; it requires emotional intelligence (EQ), empathy, and building strong relationships across the organization. A CIO with high EQ can better understand their team’s needs, concerns, and motivations, enabling them to create a positive work environment that fosters innovation and high performance. 

The short-sighted or near-sighted ‘visionaries’ leading companies and teams are holding their people in check — in many ways it’s analogous to getting stuck in traffic behind a driver that is only able to see the car in front of him and is unwilling or unable to see farther down the road,” Explains Walter Carter, President of THG Advisors and International Best-Selling Author. Compare that to the drivers who see way up the road and are quick to see emerging patterns enabling them to easily avoid traps and hazards – wouldn’t you prefer following that leader?” 

Moreover, CIOs work closely with other C-suite executives, such as the CEO, CFO, and CMO, to ensure that technology initiatives align with broader business strategies. Strong communication and interpersonal skills are essential for building trust and collaboration among key stakeholders. 

Data-Driven Decision Making 

In today’s data-rich world, CIOs need to harness data for decision-making more than ever. Modern organizations generate vast amounts of data, and a CIO will leverage this data to gain insights, predict trends, and make informed decisions. Whether using data analytics to optimize operations, enhance customer experiences, or identify new business opportunities, a data-driven mindset is essential for success in the role. 

“Data management – master it,” says Krishna Venkatesh, SVP of Saas Software Engineering, Aline. “Creating and identifying a system of record will help build a cohesive platform.” 

Furthermore, as AI and machine learning evolve, CIOs must stay ahead of the curve, integrating these technologies into their strategies to drive automation, personalization, and improved decision-making. 

Pushing Innovation and a Forward-Thinking Mindset 

The CIO’s role has evolved into that of a key innovation driver. In addition to managing existing technology, the CIO scouts for new, disruptive technologies that can give the organization a competitive edge, which requires a forward-thinking mindset, a willingness to experiment with the latest tools and methodologies, and the ability to foster a culture of innovation within the IT department and beyond. Krishna reminds us that the ability to innovate and adapt as technology and needs evolve is critical. 

“Innovate and Adapt: the tech landscape is constantly evolving,” says Venkatesh. “It is key for the leader to champion innovation and bring the entire organization on this journey.” 

Innovation is not just about technology; it’s about finding creative ways to solve business problems. A vital CIO will continuously push the boundaries of what’s possible, encouraging their teams to think outside the box and explore new ideas. This might involve implementing agile development practices, adopting open-source technologies, or experimenting with blockchain or Internet of Things (IoT) solutions. For Renee Pearson, GVP & CIO, Rollins Inc, it’s not only about pushing the boundaries, but managing the pace of innovation and change.  

“CIOs of today and in the future need to effectively manage the pace of technology innovation with the ability of their business to adopt and change, as well as their willingness to assume risk,” explains Renee Pearson, GVP & CIO, Rollins Inc. . 

Customer-Centric Approaches Are a Must 

Finally, a customer-centric approach is essential for a CIO in today’s digital age. Technology is at the heart of the customer experience, whether it’s through e-commerce platforms, mobile apps, or digital customer service channels. Prioritizing and designing the end-user experience to ensure technology initiatives enhance customer satisfaction and loyalty is a primary focus for CIOs. 

By adopting a customer-first mindset, CIOs can help their organizations stay ahead of customer expectations, driving greater engagement and long-term success. 

You need to prioritize UX and end users,” emphasizes Venkatesh. “Every task and application should be viewed from the end user’s lens and optimized with that view. Far too many times, applications are built in a way that is too cumbersome to use and proves difficult to navigate. There are several companies that do it really well, like Apple and Netflix, for example.” 

The Evolving Role of the CIO – Looking Ahead 

The CIO role has evolved into a strategic and influential position. While technology expertise remains essential, a successful CIO must possess a broad range of skills and values, including emotional intelligence, data-driven decision-making, a focus on innovation, and a customer-centric approach. By mastering these areas, along with what we covered in part one of this series, today’s CIOs will not only excel in their current roles but will also be well-positioned to navigate the challenges and opportunities of tomorrow. 

Why Smaller Boutique Executive Search Firms Could Be Better

By Retained | June 28, 2024

When you’re searching for your next exceptional leader to take you into the future of your business, the allure of partnering with a big-name search firm is tempting. Sure, their scale and content output are impressive, but is bigger always better? Small boutique executive search firms like Retained offer distinct advantages that could give you an edge in recruitment. Deciding the type of search firm you will use for an executive search is a big decision, but a small boutique executive search firm could be the best fit. We’ll explore how small boutique executive search firms can provide the edge.

Leadership Expertise

One of the biggest benefits of working with a smaller firm is that you’ll work alongside proven leaders with years of experience who have been in your shoes and know your needs. At Retained, our leaders will be involved in every step of the process, from the first call until a candidate’s placement. This ensures you get the attention and the level of expertise you deserve.

A Relationship-first Approach

When you partner with a boutique search firm, you can forge a close relationship with leadership who come alongside you to execute the search. During the process, you have greater access to leadership, benefit from their strong networks, and, as a result, are better positioned for success.

When you partner with Retained, for instance, we become an extension of your organization, guaranteeing the highest level of discretion and confidentiality. The relationship goes beyond the now; we work to ensure our clients are positioned for future success, and we maintain relationships beyond the initial search to support our clients and their continuous growth.

Going Beyond Qualifications  

Large search firms may utilize standardized processes to assess your needs and the qualifications you desire in your candidate. However, small boutique firms can go much deeper, working alongside you to understand the leadership landscape within your organization and your culture on a profoundly personal level. A Better understanding of these areas will result in the perfect fit to enhance your team and help you reach your objectives better. Knowing the client’s culture intimately also enables a more seamless transition for the leader. Our experts can coach the candidates throughout the process, preparing them to enter the role with confidence.

Specialization

When needing a search, tailoring your choice of a partner can make a world of difference. For instance, hiring a small boutique search firm specializing in the technology sector can offer you a boost if you are seeking a  Chief Information Officer or a Chief Technology Officer. Firms that specialize in a specific industry know it inside and out, and their networks often enable them to pull together a diverse pool of candidates.

At Retained, we source senior technology executives, C-suite, nonprofit, and fractional/interim executives. By specializing in these types of searches, we can put forth the optimal pool of candidates that best fit your needs. Tino Mantella, President & Managing Partner at Retained, led the largest tech trade association in North America for over a decade. His tenure not only enabled him to connect directly with hundreds of tech leaders, but he also developed an intimate knowledge of the requirements to be the best in various tech roles.

Innovation

Boutique search firms can innovate quickly without going through a maze of bureaucracy to secure approvals. While large firms have many resources, they are not as agile or flexible due to their size. Boutique firms combine innovative search strategies with robust tools and technology to ensure a successful search. A smaller firm can improve and optimize more quickly. Despite fewer resources, a more limited number of searches allows for a greater focus and allocation of resources to your account, proving to be more effective.

Bigger Isn’t Always Better

When choosing a trusted partner to find your next leader, bigger isn’t always better. While there may be some advantages to a large firm, small boutique search firms like Retained are positioned to give you a unique edge in talent acquisition. Their tailored and personalized approach, deep industry knowledge, and leadership expertise can be the difference maker in finding the perfect fit the first time. This is why you can trust boutique firms like Retained to get the job done right.