Insights from Sean Bennett, Former Citigroup Leader and Current Head of Finance & Operations at Charles IT
Introduction
The relationship between finance and technology has always been complex since you could say it’s equal parts opportunity and hesitation. While innovation continues to accelerate, many financial institutions remain cautious adopters, often hindered by legacy systems and compliance requirements. Yet with our current digital world reshaping the industry (and really, every industry), the need for strategic technology has never been greater.
That’s why, in this Southern Connecticut Thought Leadership Series, we’re partnering with influential voices from the region’s financial sector and for this article, examining the intersection of finance and technology. As for Southern Connecticut, its proximity to New York City has made it a growing base of hedge funds, private equity firms, and financial startups.
To kick off the series, we’re featuring insights from Sean Bennett, Head of Finance and Operations at Charles IT. Beyond Charles IT’s presence in Stamford, Sean brings a rare blend of firsthand financial expertise and technical strategy, with leadership roles at Citigroup, OneMain Financial, and Edge Technology Group under his belt. His unique perspective bridges both worlds, making him the ideal voice to explore how finance firms can leverage IT partnerships for transformation.
In this article, we’ll dive into the evolving nexus of finance and technology, and how managed service providers are helping financial institutions not just keep up, but lead.
The Evolving Finance Landscape in Southern Connecticut
Southern Connecticut has long served as an extension of New York City’s financial ecosystem. With its close proximity to Manhattan, access to top-tier talent, and more favorable operating costs, the region has become an attractive home for a growing number of boutique investment firms, hedge funds, and fintech startups. Stamford, in particular, has emerged as a home to an array of financial institutions that value both local roots and global reach.
Charles IT’s own presence in Stamford reflects this shift. As more finance firms move or expand into Southern Connecticut, the need for technological solutions has grown too.
“I’ve kind of seen a lot of different takes on it,” said Sean. “There are clearly similarities across different types of financial services firms and obviously some very important differences as well.”
These differences drive innovation and competition, but what unites them is the growing importance of local leadership. Firms are no longer simply reacting to what’s happening on Wall Street but shaping the future of finance right here in Southern Connecticut. That requires not just financial skills, but strong technology partnerships that can keep pace with evolving expectations around compliance, performance, and security.
Sean Journey: From Global Banking to Strategic Technology
Sean’s path into the world of finance and technology is anything but typical and that’s exactly what makes his perspective so interesting. After graduating from Rensselaer Polytechnic Institute with a degree in engineering and serving as a military policeman in the Army, Sean began his civilian career in construction management. One of his early projects? Helping to restore New York City’s iconic Grand Central Terminal.
His interest in business grew during his MBA studies though, eventually leading him into strategy consulting and later, into the world of financial services. At Citi Private Bank, he worked with ultra-high-net-worth individuals, handling unique investment scenarios and gaining firsthand experience with the specialized nature of private banking.
“The joke we had amongst ourselves was, ‘I can teach you private banking in a weekend,’” Sean said. “It’s holding rich people’s hands, and I was off onto a completely different career in financial services.”
Sean’s career evolved quickly. He took on senior roles at firms like OneMain Financial and even returned to Citi to lead the sale of a Canadian business unit. But a chance reconnection with an old friend opened an unexpected new door, becoming CFO of a managed service provider (MSP) focused entirely on hedge funds.
“It was a completely new industry for me, completely new role for me,” Sean explained. “But I loved the idea that I could drive change very quickly. Decisions made on a Monday could have an impact by Friday.”
Under Sean’s leadership, the MSP doubled its revenue and expanded globally before being sold to private equity. That success, and the desire to take on his next challenge, ultimately brought him to Charles IT, where he now leads Finance and Operations.
With hands-on experience in both traditional finance and fast-moving tech environments, Sean brings a rare hybrid perspective that’s especially relevant as financial firms increasingly rely on strategic IT partnerships to compete.
“For years, I worked in large organizations recommending change. Now I get to make decisions and see the results almost immediately,” he said.
Finance’s Love-Hate Relationship with Technology
One of the most consistent trends Sean has observed in the financial sector is the slow pace of technological adoption, especially among large, established institutions. As mentioned, between legacy systems and regulatory frameworks like SEC and FINRA, innovation often takes a back seat.
“They're hesitant to try new technologies or take on technologies that aren’t ready for enterprise-level deployment, or even well understood within a framework of compliance that applies to them,” Sean explained.
This caution makes sense. In a highly regulated environment, even minor missteps can lead to significant penalties.
At the same time, financial institutions face growing pressure from agile challengers like startups and fintech firms that aren’t bogged down by outdated systems or institutional red tape. They’re reimagining how financial services should work and they're doing so in ways that appeal to a new generation of clients too.
“Some of the biggest threats to financial services firms are fast-moving technology players who are figuring out ways to do things better, more efficiently, more client-friendly, which will ultimately displace them,” Sean said.
That paradox creates what Sean aptly describes as a “love-hate relationship with technology.” On the one hand, it’s a source of risk. On the other, it's essential for staying relevant.
The Power of the Right Technology Partner
This is where Sean’s current role and the value of managed service providers (MSPs) comes into play since MSPs help financial institutions modernize safely and strategically. What makes MSPs so valuable? According to Sean, it’s their ability to bridge an often-overlooked gap: communication and collaboration between finance professionals and IT specialists.
“The types of people, frankly, who make up financial services firms are very different than the types of people that often make up technology firms,” Sean said. “And there's a challenge in helping those two different types of folks communicate with each other to achieve whatever the firm is trying to achieve.”
MSPs like Charles IT bring the technical expertise and regulatory awareness needed to support financial firms without overwhelming them.
“A solid managed service provider with great account management, great understanding of the compliance complexities related to whatever particular financial services firm you are, can have that hand on the pulse of changing technologies and really bring that all together to drive value faster,” Sean explained.
Tailored Technology Needs Across Financial Sub-Sectors
Of course, we are using the term “financial firms” generally but it’s actually far more nuanced. Each financial sub-sector, whether hedge funds, private equity, venture capital, or traditional banking, has distinct business models and therefore…
“Different financial services, even though they're all within ‘financial services,’ have very different technology needs,” Sean emphasized.
For hedge funds for instance, technology is all about performance. Depending on their strategy, any delay in data or disruption in access could result in major financial losses.
“They have to make sure they're able to trade in the market 24/7,” Sean explained. “Latency and uptime are absolutely mission critical.”
Private equity firms, however, bring a different focus to the table.
“They want to make sure they’re maintaining and growing the value of their investments,” said Sean. “That means improving operational efficiency and security in those portfolio companies so they’re more valuable when it’s time to sell.”
Venture capital firms, on the other hand, often need help scaling early-stage technology.
“They’re asking, ‘How do we take this great nugget of an idea and make it viable, scalable, and market-ready?’” Sean said. “That’s where the right tech guidance really matters.”
Banks are perhaps the most traditional among the group.
They’re laser-focused on making sure they stay within regulatory lanes and protect their clients’ security,” said Sean. “Plus, their distributed branch networks create unique infrastructure and connectivity challenges.”
Despite their differences, all these financial entities share one common need.
“I think ultimately what they're looking for and what they most need is a partner that can bring together security focus, compliance expertise, agility with new technologies, and a client-centered mindset,” Sean concluded. “Someone who can be a true partner in bringing the best technology to bear.”
The Emerging Role of AI in Financial Services
It’s no surprise that artificial intelligence (AI) is one of the hottest topics in each of those financial services and really across all industries. For many organizations, there’s a lingering question: Is AI a threat, or is it an opportunity?
That’s again where working with a forward-thinking managed service provider becomes a major advantage. Sean pointed out that Charles IT, for example, has already started integrating AI into many of its internal processes, giving them a head start in understanding how it can be used.
“So we understand what it can do, what it can't do, what it's ready for, and what it might not be quite ready for,” Sean explained. “And we know how to wrap that in security and compliance to make sure it’s adding real value without increasing risk.”
Despite the rapid pace of change, AI has the potential to unlock significant gains in efficiency, compliance, and the overall client experience.
“What I’ve always found is that when you create efficiency within your company, more often than not, you're also creating a better experience, for either your employees or your clients,” Sean said.
Of course, greater efficiency typically translates to cost savings. But more importantly, it enables teams to focus on higher-value work. AI can handle repetitive, time-consuming tasks, freeing up employees to concentrate on innovation and decision-making.
“That may be sacrilegious for a CFO to say,” Sean joked, “but I’m really a growth CFO. That’s how you ultimately grow your business.”
While some fear that AI will replace jobs, Sean sees it differently. For him, the real promise of AI lies in its ability to enhance human capabilities.
“As a leadership team, I’m always thinking about how to make better decisions,” Sean said. “AI can help by ensuring we have the right data set, that we’re considering all the information available, and that we’re making those decisions faster.”
What to Look for in a Strategic Technology Partner
At the end of the day, choosing the right technology partner can make all the difference, especially in the finance sector, where compliance, cybersecurity, and client expectations are all high-stakes concerns.
According to Sean, a true strategic partner should do more than just manage your infrastructure. They should also deeply understand your industry, have proven compliance expertise, provide a strong, proactive cybersecurity posture, align with your strategic goals, and demonstrate a long-term commitment to your success.
“If that technology provider does that,” Sean said, “they’re going to be successful, you’re going to be successful, and it’s going to be a great partnership.”
Sean believes the foundation of growth, whether you're a financial firm or a managed service provider, lies in relationships.
“That’s always consistent,” he explained. “It’s the relationship with your customers, your clients. How you strengthen that will ultimately be a huge determinant of your company’s value and growth.”
The best technology partnerships also evolve in sync with your business goals. That means your IT provider should be able to tailor your infrastructure and technology roadmap to drive results that matter.
“If we can do that,” Sean said, “your technology naturally evolves with you. And while we’ll benefit from that evolution, more importantly, it’s being driven by your needs.”
Ultimately, the return on investment should be clear and measurable.
“Your success is driving our success and that’s a great relationship.”
Conclusion
All in all, financial institutions have a unique opportunity to gain a competitive edge by partnering with a managed service provider that understands their industry. With the right MSP, firms can elevate client experiences and confidently navigate an evolving digital landscape.
Are you a financial professional in Southern Connecticut? What’s the biggest IT challenge your firm is facing right now? Leave a comment. We’d love to hear from you and continue the conversation!
