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The Glasshammer is running a “Where Are They Now?” series where we catch up with some of the professional women who we profiled ten or more years ago. We spoke with Carey Ryan, now Chief of Staff for Citi Technology & Business Enablement at Citi, about her career evolution and the role she plays in powering the future from both a technological and cultural perspective.

Nicki: Since we last spoke, where are you now?

Carey: We last spoke for the first time about 10 years ago, which seems like a long time but feels like the blink of an eye. I’ve held a number of roles since then, all within Citi’s Technology & Business Enablement group (though the name has changed a few times).

Now, I am the Chief of Staff for Citi Technology & Business Enablement. This entails working across both our technology organization and the wider bank to ensure we are effectively communicating and implementing new technologies, both with the goal of strengthening how we work and streamlining the time it takes to get work done.

Nicki: How did you get there?

Carey: In my 20 years at Citi, I have learned the best way to grow is to embrace every opportunity, especially if it allows you to learn more about how a company works. All of the roles I have had have allowed me the opportunity to support key areas of the business, including risk and control, data, and cybersecurity, each of which are vital to ensuring impactful technology can be developed or invested in and scaled to the full firm.

Nicki: Can you share a little about your current work?

Carey: Lately, much of my focus has been driving adoption and awareness for our Citi AI tools, helping us find the best places to practically and responsibly implement AI. This work includes leading our AI Champion and Accelerator programs, which are made up of approximately 4,000 volunteers around the firm who dedicate hours each week to serve as Citi AI advocates.

I also spend a lot of time working with our technology communication teams, each of whom covers a specific but global vertical within the larger technology business. No communication initiative is turnkey, and we always work to find new ways to impactfully reach colleagues with the information they need, be it in-person mediums like executive town halls or roundtable discussions, or through digital channels like email or lobby signage. Technology is the largest organization within Citi, so it’s key to focus on communication to enable change and drive execution while strengthening our culture.

Nicki: Have there been any unexpected or interesting twists in your career trajectory?

Carey: I have always worked in or adjacent to the technology space so, even before I recognized it, I was always headed for a career in enabling companies to leverage new technology to strengthen how they operated. That said, the world looks measurably different than it did when I entered the workforce, and Citi is no different. Some of these changes came quickly, such as the introduction and integration of AI, that has demanded the need to quickly shift priorities without much advance warning.

Nicki: Have any of them taught you a valuable lesson?

Carey: Citi is a large company, so I have had the opportunity to work on many projects with many people. Given this, the two key lessons I would share that always keep in mind is to always remember the end goal of every project and to stay flexible.

Nicki: What inspires you to be a leader and your leadership style?

Carey: My favorite part of my role is collaborating with dedicated and passionate colleagues. Whether it be the implementation of cutting-edge software, the voluntary work of a small team creating new patented technology tool, or an analyst successfully completing their first rotation with the bank – it is the passionate, innovative and solution-focused people that inspire me each day.

As I have risen in my career, I strive to be a good mentor and reliable leader for all members of my team, regardless of level. I’ve been lucky to have had several mentors whose advice I still hold on to, and it’s important to pay it forward. I also can’t help but think of my teenage daughter, I want to set a positive example for her as well as for my teams of what is possible in their careers and how leaders should treat their employees. An example that, hopefully, they will one day share with their own teams and mentees.

Nicki: Since we last spoke, can you share any challenging moments, setbacks, or self-doubt you’ve experienced as well as how you have navigated them?

Carey: I’m not sure I can pinpoint just one moment, but every new challenge I am presented with comes with a bit of imposter syndrome when I do not immediately have all the answers. Almost everyday features at least one conversation about something that where either I’m not the expert or the topic is completely new to me. It can be hard to ask questions when you think everyone except you has the answer, but the ability to step out of your comfort zone and know that you add value is a skill that will never go out of style. Self-doubt is something everyone faces, and the unknown is allowed to be scary. The key is being confident in your own ability to learn and adapt to problem-solve when navigating an unfamiliar situation.

Nicki: What skills do you think will matter most for future leaders?

Carey: When I was younger, I always assumed the fear and anxiety I felt about the unknown would go away. That one day I’d wake up and know everything there was to know about my job. But you quickly figure you’ll never know it all, because the world is always changing. Instead, I found the key is to always be ready by learning how to operate effectively with uncertainty and always be willing to learn.

Future leaders must be willing to be agile and adaptive, especially as the pace of change in the world continues to increase. AI is a great example of this. It is an unavoidable technology, and we should be willing to integrate it into how we work.

Nicki: Can you share an invaluable, specific piece of guidance a mentor or someone you admire has imparted on you?

Carey: I’ve had a number of tremendous mentors over the years. What I admired most in all of them was not any guidance they offered me, but the way they all led through their actions. Each of them led with kindness and empathy, listened carefully and accepted all forms of feedback, and were more than willing to change course if something was not working.

Nicki: Has coaching supported you in your journey, and if so, how?

Carey: Yes, I’ve been very fortunate to have had several coaches throughout my career. Coaches who were mentors, coaches whose job it was to support me, and coaches who were my peers. Career coaching offers an objective view of your decision-making. This often leads to introspective reflection on ways you can reframe your thinking, which is invaluable.

We can all sometimes be so goal-oriented, but it’s critical to take a step back and reflect on if we are taking the right steps to reach these goals. I often find myself going into my coaching session with one idea of what we will talk about and coming out with an entirely new perspective. Sometimes, the external guidance that a career coach offers is what one truly needs to help unlock those ‘aha’ moments.

Nicki: We are excited to see what you do next at Citi; we wish you continued success!

“Being with my clients, helping them to get deals done, building new relationships is what breathes life into me and gets me excited.”

Ask Christina Bresani, Wells Fargo’s head of Mid-Cap Investment Banking, about a recent client visit and she’ll tell you about climbing into the cab of a semi-truck in high heels and passing a driving simulator test to show her client that she understood their business. That story captures everything about how she approaches her work: with genuine curiosity, a willingness to go wherever the client takes her, and an infectious enthusiasm that has sustained nearly three decades in investment banking.

After 25+ years as an M&A banker at two previous firms, Bresani joined Wells Fargo in 2024 as head of Mid-Cap M&A within the firm’s Global M&A business. In November 2025, she took on the expanded role of leading the firm’s Mid-Cap Investment Banking Practice focused on serving mid-cap clients and delivering investment banking products and services to the bank’s Commercial Banking clients. It’s a dual mandate she wears proudly, and one that plays an important role in Wells Fargo’s Corporate & Investment Banking growth strategy.

“When you love what you do, it’s easy to put your head down and keep doing it,” says Bresani. “But what I saw in Wells Fargo was a new challenge to do what I love and help build a leading corporate and investment bank that can bank companies along the whole spectrum of their growth – from mid-cap to large-cap and beyond.”

Building Something That Lasts

The challenge of building out and developing the Mid-Cap Investment Banking team is one that Bresani finds genuinely energizing. “Creating a strategy, building a team that’s going to be successful in the near term and the long term, is really inspiring to me right now,” she says. “That’s hiring people. It’s getting the strategy right. It’s keeping people motivated because when you are building something, it’s not always a straight line.”

She notes that the foundation of any great team comes down to one word: trust.

“The goal is to build a team with a talented group of people who have the same values and want to lock arms to be successful together. It’s not only about individual success, it’s about elevating the entire team and constantly learning from our collective successes and failures,” she says. “This has always been important to me as a leader and it’s central to Wells Fargo’s culture.”

A Career That Kept Saying Yes

Bresani started out as an analyst, fully expecting to spend two or three years in banking before figuring out what she really wanted to do. Nearly three decades later, she’s still there — and still surprised by it. “Every year I would say, ‘wow, I want to do this, I want to learn this, I want to get better at this,’” she says. “And I just kept going.”

She credits a great deal of that staying power to the mentors who showed up early and stayed. “I was really lucky in my early days to have two amazing mentors: both men. That’s important for young women in the industry to know – you don’t have to only have female mentors.” Those relationships, she says, were as much personal as professional. ” They were ‘work dads’ in the sense that they really guided me and cared about my professional and personal growth. To form those kinds of relationships really makes a difference in this business which can sometimes be tough”

The Moment That Tests You

When asked about setbacks, Bresani reflects on one of the most universal and quietly defining moments in a banker’s career: the first time a client pushes back hard.

“There is always a point in your career where a client doesn’t like you or doesn’t like the advice you’re giving,” she says. “The first time that happens, it’s really hard not to take it personally.”

Just recently, she watched a director on her team navigate exactly that situation. Rather than letting it become a crisis of confidence, Bresani chose to reframe it. “I told him: this is your pivotal moment. Here’s how we help you pick yourself up. Here’s your opportunity to really do your job.” She recalls her own version of that moment as a first-year director, when a mentor stepped in, defended her and then told her precisely what she needed to do better. “You have to learn that not everyone is going to agree with what you say, and you have to have a thick skin. But ultimately, this is a client service business. Not every client is the same, and you have to adjust.”

Fueling the Long Game

How does someone sustain nearly 30 years at that pace without burning out? Bresani takes it one day at a time and deliberately so. “It’s easy in this job to get overwhelmed with everything that has to be done,” she says. “I’m very focused on what needs to get done today, what can wait until tomorrow, and making sure I am prioritizing what is important versus being driven by what is urgent.”

But the off switch matters just as much.

“I have three children, an amazing husband, a menagerie of animals, and I am committed to exercise even if it means a 4.30am workout. I find a way to exercise because I need it. Whatever it is, it’s important to find those things outside of work that make you happy and fill your energy cup.”

Another factor to staying happy and healthy she attributes to friendship, a group forged at an all-women’s college that has stayed tightly bound across careers and time zones. “We have a text chain,” she says, laughing. “We build each other up. We laugh and say, ‘You will never believe what happened today,” She pauses, then finds exactly the right phrase for it: “It’s a group hug via text.”

Still Having Fun

When Bresani’s kids ask her about her day, they don’t want the deal mechanics. They want to hear about the people. “I come home and my kids say, ‘Mom, tell me about the people you met today,’” she says. “I meet the most interesting people.” That, more than any title or transaction, seems to be the through-line of her career. She still operates by a simple rule she set for herself long ago: “I’ll stop doing it when it’s not fun anymore. It’s still really fun.”

By Nicki Gilmour, Founder and CEO of theglasshammer.com and Evolved People Coaching.

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Powering the Future: Carey Ryan, Chief of Staff for Citi Technology & Business Enablement, Citi