Tag Archive for: General Counsel

Nancy Stern: Managing Director and General Counsel, Simplex Trading

,

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.

/by

The Future and the Women Powering It: Katherine Kirkpatrick Bos, General Counsel, StarkWare

Katherine Kirkpatrick BosKatherine Kirkpatrick Bos, General Counsel of StarkWare, is excited about zero knowledge proof technology (ZKP), a revolutionary tool in cryptography. She explains that ZKP allows people to prove something is true without revealing underlying information.

ZKPs enable verification without disclosure—complete, sound, and private. While often discussed in the context of blockchain scalability and transaction speed, their possible use extends far beyond cryptocurrencies. Healthcare records, voting systems, and government services all rely on forms of verification that routinely overshare personal data. Zero-knowledge technology offers a path to redesign those systems around privacy by default.

“StarkWare is deep, cutting-edge technology,” she says. “These are some of the smartest cryptographers and developers in the world.”

This potential drew Kirkpatrick Bos to StarkWare, a company building cryptographic systems at the frontier of zero-knowledge technology. The work is not only about present-day challenges. StarkWare has also developed quantum-resistant technology—an increasingly urgent priority as advances in quantum computing threaten existing cryptographic standards.

“Quantum computing could break a lot of what we rely on today,” she notes. “Quantum-resistant code makes that significantly harder.”

Choosing the Right Room

Prior to joining StarkWare, Kirkpatrick Bos was in listed derivatives on digital assets. She was the Chief Legal Officer of Cboe Digital, a U.S. regulated exchange and clearinghouse for spot crypto and crypto derivatives markets; and General Counsel of Maple Finance, a capital efficient corporate debt marketplace which facilitates crypto institutional borrowing via liquidity pools funded by Decentralized Financial (DeFi) ecosystems. Kirkpatrick Bos was also a partner in the Special Matters and Government Investigations practice at King & Spalding.

Kirkpatrick Bos is candid about career inflection points. She has experienced the frustration of executing a plan within a business that wasn’t growing as expected—and realizing she wasn’t in the room where the real decisions were being made.

“That’s a difficult place to be,” she says. “Especially if you believe you could be doing more.”

The response, in her view, is rarely comfort. It is movement.

“It’s much easier to stay where you are than to start over,” she notes. “But if you want growth, you have to take that risk.”

She is especially direct about this advice for women, who are often encouraged—explicitly or implicitly—to value stability over advancement.

“I’ve always approached my career strategically. You have to understand what’s next.”

Mentorship, Integrity, and Judgment

Kirkpatrick Bos credits much of her professional grounding to early mentors, including a senior partner she worked with for over a decade at King & Spalding.

“He could be prickly,” she recalls, “but he inspired loyalty through integrity.”

That lesson—never compromise ethical standards—has stayed with her. So has the importance of seeing what is possible. Senior women who pushed boundaries in their careers made abstract ambition tangible.

“If you see it, you can be it,” she emphasizes. “If others are doing it, it’s not impossible.”

The guidance she now imparts is unsentimental and practical: protect your principles, make hard decisions when required, put your family first, and outsource what you can.

Leadership in an Age of AI

As artificial intelligence reshapes professional services, Kirkpatrick Bos remains skeptical of claims that judgment can be automated.

“AI is a powerful tool,” she acknowledges. “But it can’t replace instinct.”

Over her career, she has seen lawyers develop competence through experience—and others who never do.

“Judgment is hard to teach. Problem-solving, instinct, knowing when something doesn’t feel right—that still matters.”

As General Counsel, much of her role is translation: helping regulators understand technology, and helping technologists understand the law.

“You have to listen carefully,” she says. “Then explain things in a way the other side can actually understand.”

Why It Endures

There are always difficult days. Seniority does not eliminate friction; it reframes it.

What sustains Kirkpatrick Bos is the belief that the work itself matters—that she is helping shape the legal and regulatory framework for technologies that will define the next generation.

She imagines a future where people look back in disbelief at how much personal information was once routinely shared to prove a single fact.

Innovative technology, she believes, does more than improve systems. It keeps people engaged, even when the work is hard.

And in that sense, zero knowledge is not just a cryptographic concept—it is a blueprint for more thoughtful leadership.

By Jessica Darmoni

/by

Voice of Experience: Anita Romero, General Counsel, Global Consumer, Citibank

,

Anita RomeroBy Cathie Ericson

It is who you know. That’s what Anita Romero figured out over the course of her career, and wishes that she had known earlier. “When you’re first starting out, you’re so focused on doing excellent work that you don’t realize the many benefits of seeking advice from peers in your network,” she says. “People learn over time, but had I known that up front it would have really helped.”

From Government to Finance

Romero started her career at the New York City Economic Development Corporation (EDC), which is the City of New York’s primary economic development vehicle. During her tenure with the EDC, her goal was to help keep business in the city, including the redevelopment of Disney’s New Amsterdam Theater and other magnets in Times Square.

After 12 years she went to work for the Traveler’s Group which merged with Citicorp, creating what is today known as Citi.

Since her career up to that point had been in government, she didn’t have direct product experience at a financial services firm, so she completed a rotation through different legal areas of this financial services company. She said that although the experience felt a bit like being a first-year associate again, it was valuable in helping her stretch outside of her comfort zone – advice she offers to other professionals.

“Many attorneys are very focused on a career path that only goes up, as opposed to horizontally, but sometimes doing something complementary can really help you develop, whether you are new to a job or are more seasoned in your career.”

After a year of rotation, she chose a permanent home in corporate law, principally doing securities work as well as mergers and acquisitions, an active area since the company was in a buying mode.

Subsequently, Romero worked as Deputy General Counsel of Citi’s international business segment, in which she had to face one of her first challenges, the 2002 Argentine crisis, which involved lots of “firefighting” as she says. She then returned to the corporate law department to oversee corporate legal functions that support the company as a whole, including human resources, employment law and M&A. Now, she serves as General Counsel for the global consumer business and Citibank NA, the largest subsidiary of Citigroup.

The team that she’s built at Citi is the professional achievement she’s most proud of. “We are committed to having a high-quality and diverse team,” she says. As the Legal Management Committee sponsor of the company’s Talent Development program, she actually spearheads that function for the legal department as a whole.

Technology As an Industry Game Changer

As technology evolves, so will the industry. “Startups are seeking to disrupt what we’ve been doing as banks in the digital experience, and while some do it well, they are operating under a different regulatory environment,” she says, noting that fintech entities aren’t required to be licensed the same way that banks are. “The world has changed for banks in terms of regulatory expectations, and so we are constantly analyzing and adapting to the new model.”

Romero says that Citi is whole heartedly focused on radical digitization, always seeking ways to reduce friction for customers and improve their banking experience.

Promoting Hispanic Culture through Mentoring Others

Citi supports a number of employee networks, including Citi Women, a corporate-wide diversity effort for attracting, developing, advancing and retaining female talent at all levels within Citi.

Since one of her passions is to give back to the community where she lives, Romero, who is of Puerto Rican and Cuban descent, is the sponsor of the Hispanic Heritage Network for the New York tristate area.

“It’s a terrific organization that is trying to connect network members to each other. Our members appreciate the opportunities for both networking and career development.”

They have sponsored initiatives, such as Café con Leche, where participants have the opportunity to talk with senior professionals within the organization. “They can use them as a sounding board on their career, in an intimate environment where it is comfortable to discuss their career path or other specific situations,” she points out.

“It’s all about developing and advancing our people and realizing that we can harness our different backgrounds and heritages to promote workplace success.”

/by

Voice of Experience: Heidi Stam, Managing Director and General Counsel, Vanguard Group

,

Heidi Stam“Choose something that you love because if you love what you do, work hard and learn as much as you can, everything else will come.”

Directly out of law school Heidi Stam took the law firm route as was suggested, working for a large firm and then a boutique firm. She realized litigation didn’t resonate so she switched to deal work, which she describes as the antithesis of litigation. “I loved helping two parties build a solution together,” she says.

After having her first child, though, she started debating her options and found out that the SEC was looking for lawyers. With her experience in corporate deal work, she believed it could be a good fit until she learned they were offering a position in the investment management division. Unfamiliar with that vein, she turned it down – and was surprised when two days later one of the interviewers called her and expressed their disappointment that she had passed. They offered a chance for her to come back and talk to attorneys and get a feel for the work; so instead of a day of interviews, she had two attorneys at her disposal to learn more about the role, which she eventually accepted.

“It was the best thing I’ve ever done,” she said, ultimately spending 10 years in five different positions at the SEC, which eventually led to her role at Vanguard. “You never know what will present itself to you, and being open minded and flexible can help your career.”

A Company on the “Vanguard”

When Vanguard’s CEO contacted her, she said she was particularly interested because of her high regard for the company: In her role at the SEC she had had the opportunity to see all the investment management firms and mutual fund companies in the country.

“I knew Vanguard was a special company with top-notch leadership and terrific values; it was a risk worth taking to leave Washington and join them.” She joined as head of securities regulation in 1997, and became general counsel in 2005, joining the senior executive team.

The firm has been expanding internationally and so the legal and compliance function has been growing simultaneously. Part of her role will be to build that function for the next decade, which involves working globally in different cultures and countries and through different legal systems and compliance regulations.

“We’ve embraced the challenge because we’re excited about the opportunity. Seeing the team collaborate on this work makes for a rich and exciting experience,” she said.

Other industry developments that she will help oversee include the growth of Vanguard Personal Advisor Services in which Vanguard is offering a hybrid model of a professional advisor paired with an online experience that they believe offers a superior approach at a very low cost. The service recently launched after two years of preparation and Stam believes that it’s a model that will work for investors at all stages of life. “Our mission is to offer the best chance for investment success and we think this program will deliver that. “

For Stam, the achievement she is most proud of is her ability to teach others as she grows her team. “When I look back on my career, what’s most satisfying is the ability to have touched all those people along the way. Hopefully they feel they learned something, or I put them in a better position to lead or otherwise progress.”

That achievement underscores her philosophy that a great team dynamic produces superior results. “Understanding your role within a team and what you can do to help create a strong team environment is very important as you move through your career.”

Increasing Women in Leadership Positions

Stam says that her industry seems to attract a higher representation of men than women and that creates its own challenge: women should not be daunted by the current numbers. To that end, she says she is privileged to be one of the founding members of Vanguard’s Women’s Initiative for Leadership Success (WILS), which was started seven years ago.

The WILS organization is designed to support the women at Vanguard and create an environment that fosters development and encourages women in their leadership abilities.

So far she says there has been great success, with more than 4,000 members and an increase in internal promotions as more women pursue senior leadership roles. “We’ve helped women at Vanguard see what they can do, and now we’re focusing s on external hires.”

As Stam points out, the funnel doesn’t have a high representation of women, but the company is committed to patient hiring because they know the benefits that women in senior roles offer.

Although the firm has an equal overall representation of women and men, she said that their goal is to make sure there is similar diversity in senior leadership roles. “It’s been a personal pleasure to see the number of women role models increase,” she said.

On the home front, Stam has a “wonderful husband,” and four adult children.

“The last one was a two-fer” she says, indicating her 21-year-old twin girls, as well as a son who is 26 and a daughter, 28. “I wouldn’t change a single thing.”

By Cathie Ericson

/by

Voice of Experience: Pamela Yeo, General Counsel and Senior Vice President, AIG PC Asia Pacific

Pamela YeoWelcome the The Glass Hammer’s “Spotlight on Asia” week! We will be highlighting successful women working in Asia all week long!

“Be open in your career,” advised Pamela Yeo, General Counsel and Senior Vice President, AIG Property Casualty Asia Pacific. “When you realize that everyone around you can teach you something new, and you become receptive to knowledge sharing and connecting, this can have a big impact on your advancement.”

This is one thing that Yeo wishes she had recognized earlier in her career. She urges young professionals to put themselves out there by taking the initiative to establish important connections.

Career Path

Before she became General Counsel for the Asia Pacific Region at AIG , Yeo had a long and successful career working as a lawyer in the private law sector in Singapore where she climbed the ranks from associate to partner and focused mainly on insurance litigation. Yeo transitioned into corporate counsel work after 12 years of private practice. “My work in private practice was very rewarding,” said Yeo, “but when I became aware of the opportunity available at AIG, I knew it was the right fit for me at that point in my career.”

Now, Yeo plays an instrumental role in developing the legal team in the Asia Pacific region for AIG. “We have one of the most talented teams in Asia,” said Yeo, “covering 17 jurisdictions across the continent and having counsel located in most countries.” Helping to build this team of fifty lawyers has been a major source of pride for Yeo, who is looking forward to the next chapters of growth and development for the group.

“As we continue to grow, it means that leadership opportunities and stretch assignments will be created for my team, which makes me very satisfied,” said Yeo.

According to Yeo, the emerging markets hold a lot of opportunity going forward as the industry will begin to respond to regulatory and economic developments, especially in the area of consumer protection. “It is an exciting time in the industry right now and as a company, we can identify opportunities and lead change in the future,” said Yeo.

Developing her team is something that Yeo takes very seriously. She has recently encouraged team members to participate in AIG’s pro bono program as a way to give back to the community and even develop new skills. “It is easy to get caught up in the rat race,” said Yeo, “but it is vital to take a step back and give your time and expertise to people who need it.”

Women in Business

Yeo considers herself to be lucky because she never felt any obstacles in her career advancement as a result of her gender. “I always gave my best effort,” explained Yeo, “and my talents and skills combined with my strong work ethic allowed me to progress consistently in my career on the back of tremendous opportunities presented by AIG.”

According to Yeo, AIG’s commitment to diversity has played a big role in her positive experience. She participated in the firm’s Women’s Executive Leadership Initiative which provides training, coaching, and sponsorship opportunities for executives with senior leadership potential. Yeo explained, “The program encourages 360 degree feedback through which you learn about what you are doing well in addition to the areas where you might need to improve.”

She continued, “Women benefit immensely from this type of honest feedback.”

Outside of the formal programs and the Women’s Chapter of the AIG Employee Resource Group focused on women’s career development and networking, Yeo emphasized the importance of having a supportive network of colleagues –both male and female – with whom you work every day. “Both of my bosses are male and have given me a tremendous amount of support and encouragement throughout the course of my career,” said Yeo, who said that her sponsor is also male.

“The senior management at AIG has a vested interest in the company’s diversity efforts,” Yeo noted. “They really have an active role and the amount of support they provide to all groups is truly impressive.”

Advice for Professional Women

According to Yeo, networking remains one of the most powerful career advancement tools. However, she indicated that as much as you receive from your network you should give back in the way of making yourself available to others who might need advice, guidance, or assistance.

“The Global Legal, Compliance, Regulatory and Government Affairs office, for example, has launched an Office Hours initiative where you can reach out to colleagues if you have a question or need advice,” explained Yeo, who makes an effort to volunteer to speak to participants.

Yeo also encourages young professionals to seek out as many different experiences as possible, especially working in an industry as broad as insurance. “Speak to people, get their input, and gain exposure to all of the different business areas and paths available to you,” she added.

In Her Spare Time
It is important to make time for yourself, said Yeo, who likes to attend church on the weekends as a way to clear her head and restore clarity. “This gives me peace of mind,” Yeo added. She also enjoys traveling and reading when she is not at the office.

By Michelle Hendelman

/by