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

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Carey RyanThe 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!

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Christina Bresani: Head of Mid-Cap Investment Banking, Wells Fargo Corporate & Investment Banking

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Christina Bresani“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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Nancy Stern: Managing Director and General Counsel, Simplex Trading

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Nancy Stern

By Jessica Darmoni

“The (trading) industry is built on people working together,” explains Nancy Stern. “You have to think of your interactions as long-term relationships. Something that makes sense in the short term may not serve you—or others—over time. You always have to ask: what are the unintended consequences?”

That long-term view has shaped Stern’s approach at career inflection points, business strategies and regulatory guidance. After first speaking with Stern over 10 years ago, The Glass Hammer sat down with her to talk about where she is now.

Today, as Managing Director and General Counsel of Simplex Trading, Stern stands at the intersection of market structure, regulation, technology, and leadership. She is the first, and only, lawyer at the 20-year-old market-making firm, a role that requires both precision and perspective.

Building Legal Infrastructure in a High-Speed Market

Simplex Trading operates as a market maker in the fast-moving world of equity options, where milliseconds matter and volumes have exploded. They continuously buy and sell options to capture the bid-ask spread. The firm is connected to 17 exchanges and has traders on the trading floor at Cboe Global Markets.

Over the past decade, the equity options market has transformed dramatically. Retail participation has surged. Trading volumes have exploded. Zero-day-to-expiration (0DTE) options have compressed time horizons to a single day—sometimes blurring the line between investment and entertainment for retail traders. In this environment, risk evolves quickly.

“We are in the business of taking risks,” Stern says. “My job is evaluating those risks. You have to understand the full picture—but most importantly, you have to adapt.”

Simplex historically relied on outside counsel. As the business grew more sophisticated, leadership recognized the need for an in-house legal leader to manage risk proactively, implement processes, and help shape culture from within.

Stern stepped into that role not only to mitigate legal exposure, but to build systems that support sustainable growth.

Her mandate includes implementing new procedures, strengthening governance, and aligning culture with regulatory expectations, all while keeping pace with accelerating technological change, including the integration of AI tools that are reshaping industries at unprecedented speed.

“The pace of change continues to accelerate,” she notes. “The tools are new but in many ways, the challenges are iterations of what we’ve faced before. That’s what makes it exciting to put these new tools into practice.”

From General Counsel to CEO, and Back Again

The Glass Hammer first met Stern in 2015 as Executive Vice President, General Counsel and Secretary of Allston Trading. She went on to become CEO of the proprietary trading firm, which was then acquired by DV Trading in December 2021. After the acquisition she joined futures commission merchant and clearing firm, ABN Amro, as Chief of Staff and General Counsel until 2024.

Her earlier career includes partner roles at Katten Muchin Rosenman LLP and Gardner Carton & Douglas LLP (now Faegre Drinker Biddle & Reath LLP), where she built the legal foundation that would later support her executive leadership.

Transitioning from General Counsel to CEO required more than technical skill, it required self-awareness.

“Coaching was very important to me,” Stern reflects. As she prepared to step into the CEO role, she worked with an executive coach and encouraged her team to do the same. “Understanding your strengths and weaknesses is essential. Sometimes you need someone outside your organization to help you think clearly.”

That investment in self-knowledge became a catalyst for growth.

Resilience, Realism, and Knowing When to Walk Away

Leadership, especially in high-stakes financial environments, inevitably includes moments of doubt. Stern approaches setbacks with a problem-solver’s mindset, and with realism.

“You have to ask yourself: Is this a situation I can improve? Or should I walk away? Can I make this better, or would someone else do a better job?”

She describes herself as loyal and deeply committed however she also recognizes limits. Not every system can be fixed from within and not every environment is the right one.

For women navigating leadership roles, that distinction is powerful: resilience does not mean staying at all costs. It means making thoughtful, courageous decisions about where you can create impact.

Mentorship in All Directions

When asked who influenced her most, Stern doesn’t name a single figure.

“I’ve been fortunate to have mentors at every stage and from all directions,” she says. “Senior people, junior people, peers.”

She learned the craft of law from colleagues in law firms. She learned how to lead organizations by listening to those who understood the pulse of the business and the pain points of its people.

What does she value most?

“Anyone willing to speak the truth, even when it’s difficult.”

Now, she pays that forward. Mentorship is one of the impacts she most hopes to create.

“There are people with tremendous talent who just need guidance on specific questions. If I can help them move forward, that’s incredibly satisfying.”

What the Future Demands from Leaders

As markets evolve, so must leadership. Stern believes future leaders will need empathy and the ability to put others first.

“Strong listening skills, sound judgement and the ability to sift through vast information to make principled decisions will be demanded of our leaders,” she emphasizes.

Stern also believes that execution, the discipline to turn vision into reality will be crucial.

“Vision without execution doesn’t count,” she says.

In an era of accelerating AI adoption, shrinking time horizons, and increasingly complex market participation, those human-centered skills may matter more than ever.

Leading Into the Future

What inspires her now?

“New tools. New experiences. New ways to approach old challenges.”

Despite decades of experience across law firms, trading floors, executive suites, and boardrooms, Stern remains energized by evolution.

Her leadership is not about chasing speed but about thoughtful adaptation, long-term relationships as well as clear-eyed risk assessment and helping others grow along the way.

In industries often defined by volatility, Stern’s career is a reminder that sustainable leadership is built not only on expertise, but on empathy, integrity, and the courage to continually adapt.

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Alexandra Barth: Co-Head of Leveraged Finance, Wells Fargo

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Alexandra Barth“After 25 years at one company, making a change can feel daunting,” says Alexandra Barth. “You know the people, the processes, and the rhythm of the work, it’s familiar and comfortable. But when the opportunity at Wells Fargo came along, it was so compelling that I knew it was the right moment to embrace a new challenge.”

After more than two decades at Deutsche Bank, rising from analyst to group head and becoming a trusted voice in leveraged finance, Barth was ready to trade comfort for possibility. Wells Fargo offered not just a new role but a new environment, one defined by ambition, energy, and a leadership team committed to building something world-class. For Barth, it was the right moment to make a change.

Today, as co-Head of Leveraged Finance, Barth’s work centers on building a market-leading leveraged finance franchise inside a platform that is already well-known, well-capitalized, and hungry to grow. “The firm has assembled some of the best people in the market into an established franchise that’s looking to become a true market leader,” she says. “It’s as entrepreneurial as you can be inside an investment bank, and that combination is exciting.”

Barth is drawn in not only by the business potential at Wells Fargo, but the culture, one where senior leaders regularly roll up their sleeves, model curiosity, and make themselves accessible.

“The senior management here is committed to making this not just a world-class, top-tier investment bank, but also interactive…It’s an inspirational culture. It’s not just senior leaders dictating from above or only connecting with you when something is needed” After 26 years in the industry, Barth describes the culture simply: “It’s been reinvigorating to be here.”

Barth’s path into finance had unconventional beginnings: she majored in government with an art history minor at Dartmouth. Originally considering a legal career, early law internships changed her mind, and after taking her brother up on a suggestion to try a 2-year analyst position at an investment bank, gain great experience, and reassess after that, she ended up finding that banking was where she wanted to be. As an analyst, she discovered how much she loved the pace, the problem-solving, and the client work that became foundational to her career.

Words of Wisdom: Focus on the Client and Use Your Voice

Barth credits an early mentor for helping shape her leadership philosophy, setting two expectations that she still carries: always focus on the client, and always use your voice. “The priority was to really listen to the client—what they’re saying, what they need—and not just present what you think will sound good or what’s best for the bank,” she recalls.

Equally important was the expectation that even the most junior person should contribute. “If you’re in a meeting or on a call, even as a junior person, you should be using your voice and bringing something to the table that is thoughtful and adds value.”

It is a lesson Barth incorporates into building her team’s culture. She wants her team thinking critically, independently, and confidently, not just processing.

“Banking can be very process-oriented for junior people,” she notes. “We want a culture at Wells Fargo where you take time to think about what you’re working on, ask questions, understand why you’re doing it. If you’re on a client call or a senior-level committee call, you should be contributing.”

To strengthen that culture of inquiry, Barth brings in external speakers, including investors, economists, and credit strategists, to give the Leveraged Finance team space to stretch intellectually. “We want people thinking critically,” she explains. “If something about a company or a credit doesn’t make sense, or you have a question, be proactive and ask.”

Even the physical layout of the office reinforces this ethos.

“It’s intentionally non-hierarchical. Analysts and associates sit around me. I have a managing director and a second-year analyst next to each other. People walk up and talk to whoever they need to. It’s very interactive, and I think that makes a difference.”

Honesty, Transparency, and Directness Fosters Client Trust

Barth’s track record with clients, often spanning decades and tens of billions in capital raised, rests on a simple principle: honesty.

“Being honest with clients about what you think is the best answer or solution for them—even when it isn’t necessarily most advantageous for you or your firm—has been core to my career.”

Barth’s approach is both candid and relentless. “You have to ask to lead things and be direct. Most importantly, you have to show why you deserve to win,” she explains. That means being deeply knowledgeable about the market, offering creative structures, and making clear that she and her team will be tireless advocates for clients.

Barth knows the business is complicated, and mistakes happen. What matters, she says, is how you handle them.

“The first thing you do after a mistake is what matters most. How you manage it, how you communicate, and how you teach your team to navigate it.”

Clients respond to her consistency and her clarity. Barth earns trust at the CEO and CFO level not because she tells them what they want to hear, but because she tells them what she believes is achievable and then delivers the results.

“I think the ability to back up what I say with the outcome has been one of the biggest drivers of my success,” she says. “That relationship of trust is what matters most.”

Building a Market-Leading Franchise and a Lasting Legacy

Barth sees extraordinary potential at Wells Fargo. “I think in almost every product in investment banking, Wells can be a market leader,” she says. Her goal is straightforward: to help build a platform that is viewed as a top five investment bank, across products and across markets.

As much of a priority is the experience of the people on her team. Whether they stay in leveraged finance long-term or go on to other roles, Barth wants their time on her team and at Wells Fargo to be meaningful. “At my prior firm, I’m still in touch with many of the former junior people, and they tell me their experience was a pillar of their success,” she says. “That’s what I want to create here.”

A Working Mother Who Still Makes Room for Art

Balancing a demanding role with family is no small undertaking, but Barth credits her career with teaching her how to prioritize.

“In banking, you always have ten things happening at once that you can’t possibly do at the same time. You learn to prioritize what’s most important and give it your full attention.”

Outside work, she reconnects with the passion she discovered years ago as an art history student, visiting museums whenever she can in New York and beyond while bringing her eight- and eleven-year-old children with her. “I try to teach them as much as I can about art and art history,” she says, a reminder that even amid a full career, there’s always room to nurture curiosity and creativity.

Barth aims to create that same sense of value and possibility for her team.

“I grew up in a group where every voice mattered, even junior analysts’. Now, after 26 years, that’s exactly the culture I want to create, where the smartest person on the team, no matter their title, feels empowered to speak up and knows their perspective is valued.”

By Jessica Robaire

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Deborah Overdeput: Chief Operating Officer, Innovative Systems (FinScan, Enlighten, PostLocate)

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Deborah Overdeput“I can look back and point to the promotions, the double-digit growth, all the successes along the way, but I never truly believed in my success until I stepped out on my own and built a business,” says Deborah Overdeput.

That moment of independence was not just a career milestone, but a shift in how she saw herself as a leader: someone who thrives on curiosity, creates clarity where there is none, and knows when it is time to pivot.

From Rocket Science to Market Growth

Overdeput began her career as a rocket scientist, trained in space station computing and fault-tolerant systems. Yet, when she relocated to Belgium for an engineering role at Swift, she felt restless. “I realized I really liked talking about what we were doing rather than actually building it. Once I got bit by that bug, I knew I had to transition into marketing.”

With no formal background in marketing, Overdeput made a bold decision: she would become a Chief Marketing Officer in technology. That goal guided every step she took, from mastering the fast-changing dynamics of marketing to taking lateral moves and pushing herself into stretch roles that expanded her skills and influence. At SunGard, her determination paid off as she advanced from marketing a single product line to overseeing more than 40. Later, at Sapient, she led the repositioning of a 250-million-dollar business unit and helped drive it to more than 500 million dollars in under five years.

What she took away from those years was simple: strategy only works if it is rooted in reality. “If you do not understand how products work, how teams operate, and what customers actually need, it is hard to make the right choices. I have always believed strong leadership starts with really knowing what is happening on the ground.”

Creating Clarity in Uncertain Times

Overdeput believes leadership matters most when circumstances are ambiguous. “You do not need leadership when everything is well defined. You need leadership when the path is unclear and the pressure is high. My role has always been to take that uncertainty, translate it into strategy, and help others see the way forward.”

That principle carries into her role today as COO at Innovative Systems, where she leads global product management, marketing, operations, and human resources. “My focus is on enabling human potential by aligning talent, strategy, and resources so that even in shifting markets, our people can do their best work and deliver meaningful impact for our clients.”

Innovative Systems is also known for building long-term relationships with clients, some spanning decades. Overdeput emphasizes that trust is both a differentiator and a responsibility. “Our clients count on us not just for technology, but for partnership. Delivering on that promise, year after year, is what keeps us relevant and resilient in a shifting compliance landscape.”

Lessons in Confidence and Voice

Before her COO role at Innovative Systems, Overdeput built a successful consultancy as a fractional Chief Marketing Officer. Working with a range of technology and financial services clients, she discovered a new level of confidence in her own capabilities. The experience affirmed her expertise and sharpened her ability to deliver high-impact results across different businesses and industries.

She also discovered her voice had changed. “Earlier in my career, as a woman inside large companies, I often found my ideas ignored until repeated by a man. Over time, I learned to strengthen my voice, to claim my authority. Today, people stop and listen not just because of my title, but because they know I speak with conviction and experience.”

That conviction shapes her leadership style today. “I try to listen more and advocate for voices within the company. Leadership is not about being the loudest person in the room. It is about making sure the right voices are heard.”

The Power of Networks and Mentorship

For Overdeput, networks and mentorship are essential leadership tools. She has mentored University of New Hampshire students since 2009, often those with math or computer science backgrounds like her own. “I tell them, start early. Build your network, get on LinkedIn, connect with your peers. Those relationships are career changing.”

Mentorship, she says, has shaped her as much as her mentees. “Working with students helps me see how the next generation thinks, what motivates them, and how they want to grow. That perspective is essential for any leader who wants to build teams that are not only high-performing today but also ready for tomorrow.”

It is also what inspired her latest project: Walk Away, a book she is co-authoring with Sally Clarke. “The book brings together stories of women who reached pivotal moments and chose to leave situations that no longer aligned with their values or ambitions. Hearing these stories has been like sitting with different mentors. Each one has helped me rethink the situations I face in my own career and the challenges my mentees bring to me. One of the women said, ‘Walking away was the boldest form of leadership I have ever practiced.’ That stayed with me, because leadership is often about knowing when to stay the course, and when the braver choice is to step into something new.”

Building Teams Through Talent

For Overdeput, the heart of leadership lies in building strong teams. “High-performing teams are not built by accident; they come from spotting potential others might overlook and giving people the chance to prove themselves. One of my best hires did not meet the checklist on paper, but I knew she had what it would take. She went on to become a star. As Steve Jobs once said, it does not make sense to hire smart people and then tell them what to do. My role is to create the conditions for their talent to shine.”

Her approach is less about rigid processes and more about creating conditions for people to thrive. Weekly check-ins, open conversations, and celebrating wins keep teams connected and aligned to a bigger purpose. “One of the most rewarding experiences is when a team pulls together to deliver something bigger than any one individual could achieve. I make it a point to celebrate those moments, because they remind me that leadership is not about one person’s actions, but about creating the environment where everyone’s contributions matter.”

Leading With Intuition and Humanity

Her leadership philosophy is also shaped by yoga and meditation, which she has practiced for more than 30 years. “Yoga taught me how to breathe through stress and build core strength, not only physically but also in the way I show up as a leader. Meditation taught me to quiet the noise, to see the world beyond my own ego, and to stay present for others. Together, they remind me it is not about me, it is about enabling others. Maya Angelou captured it best: people will forget what you said and what you did, but they will never forget how you made them feel. That truth stays with me, because I have seen it reflected back in the people I have supported, watching their success become part of my own impact.”

And from her mother, she learned the value of having a cheerleader in your corner. “She showed me that sometimes what you need most is someone who believes in you, no matter the obstacles. That is the kind of leader I try to be for others.”

Looking Ahead

Asked what drives her today, Overdeput points to impact. “I want to look back and know I left a stamp, that I built teams, grew businesses, and created opportunities for others to succeed. For me, leadership is about enabling human potential in ways that last, so the people and organizations I have touched continue to thrive long after I have moved on.”
That philosophy ties her trajectory from rocket science to COO together. As she puts it: “Great leadership means building great products, growing great people, and creating clarity in a complex world.”

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Nicole Young: Head of CRE Portfolio Management, Wells Fargo

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Nicole Young“At the end of the day, the impact I care about most is on people, helping them achieve what they didn’t think was possible and elevating the organization to new levels,” says Nicole Young. “The efficiency, output, and success that result from bringing out their best work are just byproducts of that focus.”

Young is a leader whose passion lies in transformation: unlocking potential in people, teams, and entire organizations. She shares how this mindset has guided her career, from CMBS to consumer lending and back to commercial real estate, where she now leads Wells Fargo’s portfolio management organization.

Building from the Ground Up

With nearly thirty years in commercial real estate at Wells Fargo, Young has navigated multiple facets of the business, from underwriting and origination to credit approval and even workouts during the Global Financial Crisis. Each role sharpened her expertise and resilience, but more importantly, it revealed her talent for building and shaping something from the ground up.

“I was fortunate to be asked to start from scratch and lead our small loan CMBS (Commercial-Backed Mortgage Securities) program, which focused on loans between 1 million and 15 million,” she recalls. “I started the group, structured how it would work, hired the people, developed the process. That was really fulfilling…it’s where I got the taste for building something from the ground up.”

After fifteen years in CMBS, Young made a pivotal decision to move to Wells Fargo’s consumer side, leading underwriting for the home lending group. The transition required scaling her leadership from 20 people to more than 1,700 while transforming the organization to be more efficient and effective. “That was a steep learning curve,” she says. “I had to really learn to lead with data… and understand how standardized processes are critical to making an organization of that size run efficiently and effectively.”

When Kara McShane, Head of Commercial Real Estate, asked her to return five years later to take on a role that demanded both large-scale leadership and efficiency shaped from the start, the decision was an easy one.

“I had always admired Kara’s leadership and knew I would love to work for her. When she contacted me about coming back to CRE, I was thrilled.” She continues, “Wells Fargo had recently consolidated its commercial real estate lines of business, but no one was managing the portfolio as a whole and making sure those businesses were acting and making decisions as one. There was a huge opportunity to create efficiencies through standardization, and I got to build the new Portfolio Management organization from the ground up.”

Today, Young’s group of nearly 400 professionals oversees capital strategy, underwriting, closing, and portfolio management, bringing consistency, efficiency, and risk mitigation across the organization.

“Kara’s vision of bringing those groups together and leading them as one unit has really paid off given that we are rated the #1 Global Real Estate Bond Bookrunner, #1 CMBS, #1 Bank Agency lender, #1 Construction lender, and #1 in Loan Syndications.”

Learning to Lead at Scale

As Young progressed into senior leadership, she quickly realized that success required developing new skills, most notably, learning how to lead at scale and communicate effectively across large, complex organizations. When she transitioned to leading a team of 1,700, she remembers her boss giving her valuable advice that fundamentally shifted her mindset.

“He said, ‘I need you to lead the people, not the work’…it really shifted me from feeling like I needed to be the subject matter expert to recognizing that I’m here to lead the people. They can be the subject matter experts. My job is to guide them, give them the vision, and make sure the organization is moving in the right direction.”

Young notes that another key part of leading at scale is mastering communication in many directions: down to the team, out to the organization, and up to executive leadership.

“With my team that means ensuring they understand the vision, are aligned around the priorities and the mission, and are inspired to do their best work to deliver for our clients. To do that, I spend a lot of time with the team individually and in groups.”

In communicating up and out to executives, regulators, and the board, Young explains, “It’s about taking the complex and making it simple, understanding your audience, and tailoring your message with the right level of detail.” For Young, effective leadership at scale depends on both connecting with her team and translating that insight for the broader organization.

Authenticity and Grit

Young’s experience learning to lead at scale also reinforced a few key traits that have consistently supported her success. Young attributes much of her leadership growth to a willingness to embrace new challenges and learn continuously. “I’ve taken on different roles throughout my career where I didn’t necessarily have deep expertise,” she says, “but I was always willing to dig in and figure it out. That willingness to learn and to tackle hard challenges is important.”

Young also points to authenticity as foundational to her approach. “I don’t put on a façade…I’m direct and frank, which some people like and some may not, but this is the real me. I lead my team that way, and I try to always be honest and transparent.” That straightforward approach, combined with high expectations, has helped her bring out the best in the people she leads. “One of the things I’m most proud of is the team I build and what I can help them achieve.”

Finally, grit and drive are an important part of the mix. “You can’t underestimate the power of hard work,” she notes. “It has served me well throughout my career.”

Believing in Others as They Believed in Her

While Young’s drive, authenticity, and willingness to take on challenges were essential building blocks to her career progression, she is quick to credit the support she received from both Wells Fargo and the people around her. Early on, she balanced career ambitions with family responsibilities, working part-time as a young mother while continuing to excel in her role.

“People saw my potential and believed in me—Wells Fargo believed in me—and were willing to wait until the time was right for me to step into bigger roles…I appreciate that I was given the time and space when I needed it and I try to do the same for my team.”

Now, Young pays that support forward. “When I see someone’s potential, I bring them in, help them develop, and give them a platform to grow. Sometimes that even means helping them move to other parts of the organization where they can expand their skills.”

Bringing Out the Best

The commitment to lifting others up naturally extends into how Young leads her own team. A defining principle of her leadership is written clearly on her whiteboard: What did I do today to make the team better?

“I spend time really trying to figure out what motivates people individually and collectively as at team to bring out the best in them. I give stretch assignments that get them to do more than they think is possible,” she explains. “When they’ve done the work, I make sure they’re the ones presenting it. They deserve the visibility and the access to other leaders.”

That people-first philosophy is both Young’s leadership signature and her source of fulfillment. She finds meaning in seeing her team grow, whether it is employees she once hired fresh out of college who are now thriving across the organization, or former team members who choose to come back and work for her again. “That to me is amazing,” she says. “Seeing people’s success and knowing you had a part in getting them there is truly fulfilling.”

Even after building multiple teams and functions, Young remains motivated by challenge and transformation. “We have a few more years before this group is a completely well-oiled machine… but it’s exciting to see the impact. Ultimately, success isn’t just efficiency—it’s the growth and fulfillment of the people I lead.”

By Jessica Robaire

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Angela Cruz: Sales Effectiveness Leader, Sales Excellence, Accenture

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Angela Cruz“One of my love languages is acts of service, and at work, I manifest that through mentoring, supporting career advancement, anything that fosters engagement,” says Angela Cruz. “It’s how I bring to life a part of me that’s very important to my soul.”

For Cruz, the work matters, but it is the people, the learning, and the community that make it meaningful. She shares how through every chapter of her journey, authenticity, connection, curiosity, and service are the compass guiding both her growth and her leadership.

From Technical Skills to Personal Alignment

Moving from the Dominican Republic to the United States at fifteen, Cruz faced the dual challenges of learning English and adapting to a new culture, yet she remained optimistic about the possibilities ahead. She started her studies at a community college, the most affordable and accessible option, and explored different paths before settling on electrical engineering. The choice was pragmatic rather than inspired. “It wasn’t a calling,” she reflects. “I wanted to finish college with a career that had a financially stable future, and technical careers were very well paid.”

That practical decision laid the foundation for Cruz’ first professional chapter at AT&T Bell Labs, where she spent 15 years. She describes it as “like what working for Google or Apple is today,” a place defined by PhDs and cutting-edge innovation. “That’s where I grew up professionally,” she says. But just as important, “that’s where I also learned about corporate culture… to get involved in passion projects that contributed to the culture of the team and the company.”

After more than a decade in technical roles, Cruz realized her personality aligned more naturally with business development. Marketing became a bridge into sales, where she discovered the work felt intuitive. “Sales isn’t something you really learn in a university,” she explains. “It was something I evolved to, and it had a lot to do with my personality—my ability to connect people and build relationships, which is the heart of what sales is.”

Cruz’ combination of technical grounding and people-centered skills propelled her into sales leadership across the telecommunications and software platform landscape. Today at Accenture, she brings those same strengths to her role as Sales Effectiveness leader for Sales Excellence.

“I’m in a sales-effectiveness role, helping account teams bring innovative solutions to clients, all anchored on GenAI and Agentic Architecture. To be in a role that is so relevant to what’s business reinvention and transformation– it’s a huge privilege.”

Connection, Adaptability, and Purpose

The qualities that have carried Cruz forward extend well beyond relationship-building; she describes how cultural alignment, adaptability, and purpose also play a defining role.

“I learned at a certain point in my career what my strengths were in terms of cultural alignment. When I transitioned into sales, I worked a lot with Caribbean and Latin America, which is where I come from. Having the dual language and the cultural sensitivity gave me an edge in navigating that transition, which was very motivating for me.”

That shift into sales also coincided with a move from New Jersey to Miami, which tested and reinforced her adaptability. “Flexibility, being open to adjust to different environments, adapting to new circumstances, it’s something I learned very early on, and that trait has helped me along the way as I navigated my career.”

While connection and adaptability opened doors, purpose is the force that sustains Cruz.

“Every company I’ve been at, I’ve always combined my responsibilities with volunteer work both within the company and within the community. That’s what has kept me with a high level of enthusiasm for what I do. I always need to have the two: not just the job, but also the engagement.”

Leaning on Guidance

As much as Cruz’ strengths have contributed to her achievement, so too are the people who believed in her potential. “I’ve always had a personal board of directors. Some people come into your life for a season, for a reason, or for a lifetime. I’ve had all those types of influences.”

Cruz highlights the mentor who gave her a chance when she had no sales experience and sponsored her move to Miami. “I experienced impostor syndrome in the beginning, but his encouragement eased the transition.  He’s always been invested in my success and has been there through every career milestone.”

That kind of support has remained important at every stage of her career. When Cruz joined Accenture through an acquisition, she recalls how overwhelming the transition felt. “When you come as a group that was just acquired, you’re completely lost. But I was fortunate to work with people like Alex Tyler, a Managing Director and extraordinary leader who was kind, patient and recognized my value.”  Those experiences of being championed are at the heart of why she invests so deeply in others. “I know the power of sponsorship, mentorship, and advocacy. I’ve fully taken advantage of it, and that’s why I feel so strongly about paying it forward!”

Family is also a grounding force. Cruz credits her grandmother, now 101, as a pillar and role model. “She had 13 kids, and now there are about 169 family members over five generations. She’s taught me resilience, strength, faith, and positive mindset. She loves music, she’s witty, light-hearted and full of joy. She’s been a huge influence and my source of inspiration.”

Bring Your Full Self and Build Community

Nearly four decades after making the pivotal decision to study electrical engineering, Cruz was invited to return to her alma mater to deliver the commencement address.  Speaking to over 1,800 graduates, many from underrepresented backgrounds, her message was both simple and profound: “Always be proud of who you are, and bring your full self to whatever environment you’re in. It’s what makes you unique, and the world needs you as an individual and what you bring to the table.”

Second, she highlighted the importance of building community. “I’ve moved and started over several times. Managing those transitions successfully is only possible when you make community, when you connect with people, when you find affinity and appreciate differences. The differences are where you learn.”

For Cruz, this same principle applies in business. Networking, she explains, is less about career advancement than about deepening understanding. “That’s where you really learn –when you connect with people in different companies that do different things than you do. It enriches you as a professional and as a person.”

Continuous Learning, Lasting Pride

Even at this stage of her career, Cruz challenges herself to try something new, recognizing that part of her success is a willingness to evolve. “Continuous learning has been a key driver,” she reflects. “I have reinvented myself quite a few times because I’ve always been open, flexible, and curious to learn.”

Her current position at Accenture is a clear example of that mindset in action. “This was a stretch assignment for me. While I had worked in Sales Operations in the past, the scope is much broader here, in fact is called Sales Excellence for a reason, best in class. There was a lot I needed to learn… and I said, yes, I’ll do it.”

Cruz reflects on the impact of that choice. “Fast forward one year, I feel very privileged and successful, because I helped the team achieve the goals the firm established. It fills me with a lot of pride.”

When it comes to her greatest accomplishment, however, Cruz does not look to her career. “I have very strong family values and my kids are a huge source of pride for me. They are grown and very successful professionals – my older son is in cybersecurity at Zendesk, my younger son is a digital content producer with the Miami Heat, and my daughter works for the president of TelevisaUnivision. I raised them as single parent, and to me, that is, besides work or anything else, my biggest accomplishment. They are my anchor and my beacon of light.”

By Jessica Robaire

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Johanna Diaz: Global Head of Alternatives Product Strategy, Goldman Sachs

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Johanna Diaz“In facing challenges or change, I always go back to the questions: Am I in the right place? Am I surrounded by the right people? Am I learning? Am I growing?” says Johanna Diaz. “When you can identify core tenets to return to and hold yourself to them, they become a guide for navigating almost anything.”

Led as much by her intuition as by the foundational aspirations of her first-generation beginnings, Diaz leverages every opportunity to learn, grow, and lead. She shares how her trajectory reflects not only her resilience but also the support of mentors whose influence continues to inform her leadership.

From the Bronx to Goldman Sachs

Born in the Bronx to parents who immigrated from the Dominican Republic, Diaz understood the value of education from an early age: “being a first-generation American, my parents made it a priority for my siblings and me. We were the first in our family to attend university and enter the business world.”

For Diaz, that focus on education was also a path to financial stability, which led her to pursue accounting — a profession she saw as both practical and reliable. Starting her career first as an intern and then as a CPA at Grant Thornton, Diaz gained both skills and exposure. When she was first introduced to Goldman Sachs as a client of Grant Thornton, the experience left an impression.

“I was blown away by the caliber of the people, the rigor around collaborative teamwork and the focus on delivery.” That exposure opened her eyes to possibilities beyond what Diaz had imagined. When the opportunity came to join Goldman, she took the leap. “That was the first big twist in my career as it redirected my vision from accounting to a whole other world of possibility.”

Over the next two decades, Diaz’ career grew organically across business development, research, and ultimately asset management to be the Global Head of Alternatives Product Strategy, a role that she finds equally rewarding and inspiring.

“The last five years have been so incredible, pivoting to the alternative investing landscape. I’ve had the opportunity to help build a business from scratch and expand the shelf as it relates to our products. The content, as well as being a part of a team that is integral to Goldman Sachs’ growth has been so fulfilling.”

The Influence of Mentors and Executive Coaching

Diaz credits her ability to pivot, take risks, and grow in new roles as being bolstered by the mentors who offered guidance and perspective along the way. An early mentor gave her a piece of advice that still resonates: take stock every few years.

“That conversation was pivotal for me. Even 20 years later, every two to three years, I take a personal moment of deep reflection: Where am I? Have I accomplished what I set out to do? Could there be more? That practice has guided me throughout my entire time at Goldman.”

She sees mentors as a personal “board of directors” — people who know her well and can be honest when she calls on them for guidance, whether about career decisions or balancing family and work. “My mentors played a huge role in helping me navigate my personal journey, including building a family, while building momentum in my career.”

Executive coaching complemented that support, giving Diaz structured feedback and tools to grow. Early programs offered through Goldman helped her refine presentation skills, while later on she focused on refining “leadership and communication skills but in a more nuanced way than I’d ever had before.”

Together, mentorship and coaching have provided Diaz with both a trusted sounding board and a framework for continuous growth, shaping the leader she is today.

Values-Driven Leadership

Beyond the mentors and coaches who helped guide her, Diaz points to a foundation of authenticity and integrity as key to her success.

“First and foremost, it’s important to remain true to yourself,” she says. “All of my values anchor around being a good human and working with high integrity. They guide me through everything I do.”

Fairness is equally central. Diaz strives to create a work environment where people feel valued, connected, and confident that they will be treated justly. “I want to be someone people feel comfortable approaching,” she explains. “They should know I’ll listen and provide support.” Drawing on lessons from leaders she has worked with, Diaz shapes her leadership around trust, relationship-building, and followership.

Hard work and high standards also define her approach. She believes in delivering quality work with reliable outcomes and modeling excellence to inspire her team to do the same. “As a baseline, I expect that not only of myself, but it’s also important to me to set the right example that my team then wants to follow,” she notes.

Embracing Risk

While Diaz’s career has been marked by achievement, it has not been without moments of uncertainty. She recalls these moments as an opportunity to pause and reflect.

“Early on, I faced a decision about whether to continue in research or move toward a more strategic, leadership-focused role. It was uncomfortable because I wasn’t sure I’d excel, but I leaned on my core values and trusted mentors to guide the decision.”

Over time, Diaz has learned to embrace risk thoughtfully, viewing it as an opportunity to challenge herself and explore new possibilities. Her recent transition into asset management illustrates this approach. Encouraged by a mentor to consider another part of the firm, she reflects, “it was through that conversation that I realized that it was time to take a risk. I was super comfortable. I had a lot of security. I had to consider, ‘do I want to push myself a little more?’”

Deciding to “take a risk on herself” and accept the opportunity to become the COO of Goldman’s growth business, Diaz says, “was a big transition. But it pushed me, and it’s been the most pivotal part of my career.”

Legacy of Access and Opportunity

Looking ahead, Diaz is focused on creating opportunities for others to grow, much like she was supported throughout her career. “I hope to provide a platform for the teams I work with, and for the junior professionals I mentor, where they have access, exposure, and opportunity the way I did.”

Reflecting on her own journey, Diaz acknowledges how her first-generation roots are a part of shaping this commitment. “We really have lived the proverbial American dream. My parents grew up on a farm — my mom one of 12 kids, my dad one of nine — and through a combination of hard work, timing, and a little luck, we’ve seen growth that isn’t just financial. It’s also about access to the world, to opportunities that otherwise wouldn’t have been organic. It’s important to me and my family to pay it forward.”

Thanks to the holistic support embedded in Goldman’s culture, Diaz also makes an impact beyond the firm through programs like 10,000 Small Businesses. “Having the opportunity to serve as a mentor in the program, I have listened to small business owners’ pitches and given feedback—providing people with access that they otherwise wouldn’t have.”

Ultimately, Diaz measures her legacy by the people she supports. By combining high standards, integrity, and a values-driven leadership style, she aims to cultivate talent, inspire confidence, and foster a culture where people feel valued, challenged, and capable of achieving their potential.

“If, 20 years from now, I can look back and see that the people I touched built successful, meaningful careers, then I’ll know I’ve done my part.”

By Jessica Robaire

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Heather Plumski: President, Stearns Bank

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Heather Plumski“I lead with integrity and faith,” says Heather Plumski. “That means being honest, thorough, and accountable.”

As President of Stearns Bank, Plumski brings a rare blend of head and heart. She shares how her leadership is driven by values, grounded in purpose, and distinguished by forward thinking with a readiness to own both the good and the bad.

From Part-Time Teller to President

Plumski’s journey started in forensic science before pivoting to accounting, completing her degree in two years. While classmates chased big-city roles, she chose central Minnesota and a part-time teller job that turned into a career.

“I didn’t even know what a credit analyst was,” she recalls. “But it let me work with numbers and small businesses both objectively and subjectively to understand their needs…which I found to be incredibly rewarding.”

Since joining Stearns in 2005, Plumski has led through every phase from underwriting through the Great Recession to helping build the SBA and equipment finance programs. As CFO, she drove strategy. Now, as President, she leads a women-owned, employee-owned institution committed to helping people reach their full financial potential.

“We walk the walk. As employee-owners, we understand the challenges our customers face, and we build solutions that serve them.”

Authentic, Inclusive Leadership

Plumski’s leadership style is rooted in authenticity. “You can’t fake it,” she says. “When you’re aligned with who you are, your decisions get clearer, your leadership gets stronger.”

Her collaborative approach encourages open thinking. “I used to wait until every idea was perfect. Now, I bring it to the table early. It invites feedback and makes the work better.”

She credits her growth to staying curious and stretching beyond her comfort zone. One major stretch? Leading technology. “It was like learning a new language. But I learned I didn’t need to know everything I needed to trust the experts around me.”

Just Keep Going

Plumski pushes back on perfectionism and encourages boldness. “Women often hesitate if they don’t check every box. My advice? Don’t count yourself out – say yes before you say no.”

Her mantra: “Don’t quit on a bad day.” That resilience, she says, has made all the difference.

Coaching, Clarity, and Perspective

Executive coaching has been a game changer for Plumski. “It pulls me out of the weeds. I walk away with clearer thinking, stronger communication, and better perspective.”

Even when she feels too busy to take the call, she never skips it. “I always leave better than I came.”

Empowering Employees, Growing Communities

Looking forward, Plumski is focused on deepening Stearns Bank’s impact from growing employee ownership to expanding inclusive financial solutions nationwide.

“Our Employee Stock Ownership Plan isn’t just a model. It’s a movement,” she says. “When we help our customers succeed, our employee-owners build generational wealth.”

That sense of shared prosperity also drives Stearns’ focus on underserved markets. “We listen first. Then we build whether it’s through our Salaam Banking Division or nonprofit solutions. And by the time the rest of the industry catches up, we’re already on to what’s next.”

Family and the Mountains

When she’s not leading a national bank, Plumski is hiking, running, canoeing and simply soaking in family life with her four kids, husband and extended friends and family.

“There’s something about the mountains,” she says. “They remind me how small we are, and how big our purpose can be.”

By Jessica Robaire

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Marie Bober: Chief Compliance Officer and Senior Counsel, Moelis Asset Management

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Marie Bober“I naturally step into a role when there is a dearth of leadership,” says Marie Bober. “It’s just part of who I am – I see the need and think, ‘I got it.’”

From captaining sports teams as a kid to speaking up in moments of silence, taking charge has always felt instinctive for Bober. “I come from a really long line of very bossy women,” she laughs. “I think it’s probably genetic.” While her grandmothers ran their households with authority, her mother broke barriers, becoming one of the first women to earn a PhD in chemistry from NYU in 1972.

That inherited sense of purpose shaped Bober’s own unconventional path. She started college as a chemistry major but quickly pivoted to psychology. Drawn to forensic work, she earned a master’s and spent three years at a pediatric psychopharmacology lab at Massachusetts General Hospital researching ADHD and pediatric bipolar disorder.

“My plan was to go on to get my PhD, but research itself started to feel like a tough long-term path with low pay, questionable ethics in some corners, and not a great ROI if you wanted a sustainable career.”

Still captivated by the intersection of law and human behavior, Bober pivoted again, this time to law school at Northeastern University. Being a part of Northeastern’s distinctive co-op program allowed her to try a little bit of everything: working with a solo practitioner, in a judge’s chambers, the DA’s office, and an in-house legal team.

“In-house was by far my favorite, but you don’t just go from law school to in-house,” says Bober. Instead, she built her experience through small firms, auditing work, and ultimately opened her own practice while keeping her eye on the long game.

Bober’s diligence paid off when a friend offered her an in-house legal role at Gracie Asset Management, a Moelis subsidiary. The only catch was the job was in New York, which meant that Bober and her wife had to live long distance for a few years. When Gracie had a key man event resulting in steep layoffs, Bober moved over to the parent company. After a few internal moves – and the sudden loss of a friend that left a senior counsel role vacant – she was promoted into her current role as Chief Compliance Officer and Senior Counsel at Moelis Asset Management.

Breadth that Delivers

Looking back on what has helped her succeed, Bober points to adaptability and a breadth of knowledge, both of which are essential in a role that spans legal and compliance.

“To be in this particular role, you can’t be rigid or precious,” she explains. “We’re an entrepreneurial business…everybody’s got to do a little bit of something, and you have to be okay with that. We’re always thinking about new strategies, markets to tap and ways to get clients. It’s flexibility and a willingness to pick up the next thing and learn.”

Bober points to the growth of the business as another part of what requires adaptability: “when we started, we were private equity. Now we’re private equity, broadly syndicated loans, direct lending, seeding of emerging managers, venture capital.”

As the business expands, so too does Bober’s knowledge base, which is necessary for her to guide legal and compliance issues.

“I call myself a triage nurse because there are certain areas that I’m deep in, like fund formation or structuring, but then I also have to be able to direct counsel for things like litigation, tax matters, or employment. I might not be an expert on all those issues, but I must be conversant enough so that my subject matter experts can direct me effectively.”

What They Didn’t Teach in Law School

Beyond technical range and flexibility, Bober believes that one skill rises above the rest when it comes to lasting success: knowing how to navigate people.

“How to handle and approach people is key; it gets you so much further than even your technical knowledge,” she emphasizes. “One of the things law school doesn’t teach you is that if you’re a practicing lawyer in a firm, networking is 98% of your job. To be a partner at a law firm means that you bring in a good amount of business.”

Bober adds, “My boss likes to joke that he thinks that my psych degree sometimes helps me more than my law degree because it definitely gives you a framework for understanding people.”

That understanding shapes the way Bober communicates, builds relationships, and earns trust, especially in the context of leadership and knowing how to manage in all directions.

“Managing up is a skill that’s rarely taught, and it matters just as much as managing direct reports. I’ve learned how to communicate differently depending on who I’m talking to, and how to present something in a way that gets the right response.” As Chief Compliance Officer, she often needs people to act on specific requests and ideally, do so with genuine buy-in. “I’ve seen people try to lead through fear or pressure, but that only works for so long. Eventually, people tune you out.”

It is a message she impresses on junior staff as well: “be proactive, message appropriately, be polite and respectful, and if you make a mistake or get it wrong, have the ego to walk it back and take responsibility. It builds trust.”

Leadership as a Team Sport: Fostering Growth Over Competition

In an industry known for individual ambition, Bober takes a different approach to leadership; one that is shaped by hard-earned lessons and a clear sense of the kind of environment she wants to create.

“I’m a competitive person,” she says, “but I try not to be competitive at work. That’s not the environment I want to foster.”

Earlier in her career, Bober saw firsthand how toxic leadership can erode trust. She recalls a former manager who guarded her influence closely and refused to use any of her political capital to support others.

“When my mom passed away, I got two days of bereavement. Other department heads had given people the full week, but my boss told me if I wanted the extra time to attend the funeral, I’d have to use vacation days. She didn’t want to spend any of her political capital justifying why I was not billing or there for that week.” That experience left a mark, but also a guidepost: “It taught me exactly the kind of leader I don’t want to be.”

Now, as a senior leader herself, Bober sees mentoring others not as a threat, but as part of what defines strong leadership. She draws inspiration from Brazilian Jiu Jitsu, a sport she trains in outside of work.

“My coach always says he never hides the best parts of his game because if someone can master it in two weeks and beat him, they deserve to win.” The same philosophy, she says, applies in leadership. “Helping my associate grow, bringing her along and giving her what I can to help her succeed doesn’t threaten me; it strengthens the team, and if I ever move on, she’s ready to step in.”

Success, On and Off the Mat

Whether she is preparing for a Brazilian Jiu Jitsu tournament in New Jersey or aiming for another podium finish at Masters Worlds in Las Vegas, Bober brings the same focus and drive to the mat that she brings to her role at Moelis. A two-time Masters World Champion as a brown belt and now a black belt competitor, she thrives on the discipline and challenge of competing and on the fulfillment it brings outside the office.

That mix of ambition and purpose is intentional. “I strove to have an in-house position. I strove to have work-life balance in my career,” she says. “And I think I’m in a spot where I can do both.”

For Bober, success is not about chasing the highest title or the biggest paycheck. It’s about feeling grounded, challenged, and able to pursue what matters. “I can sing in a rock choir on Tuesday nights. I can do jiu jitsu. That’s what makes it all worth it.”

By Jessica Robaire

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