Ethical Leadership Spotlights

10 Questions With Holy Cross' Next Generation Of Leaders

Holy Cross alumni are making a difference in a variety of industries, and many of the College's alumni have found themselves in professional leadership roles. We've spoken with over a dozen people who graduated from Holy Cross between 2003 and 2015 and asked each of them 10 questions. Here's how their time of The Hill shaped their worldview and their professional approach.

Alesandra Mclean '09

Tell us about your job role and employer. What are you currently working on?

In my role as Director, HR Business Partner at Moderna, I lead the strategic connection between the business and Human Resources. I partner with leaders across two key functions — Global Regulatory Strategy and Clinical Assays, Supplies, and Logistics — to design and implement organizational strategies that position Moderna for success five to ten years into the future. My work spans the full spectrum of HR activities, including: performance reviews, total rewards, headcount planning, engagement and sentiment analysis, employee relations, and other talent initiatives that help shape Moderna’s future-ready organization.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

Holy Cross has influenced every step of my career and shaped my professional aspirations. Coming from a community of exceptional students and faculty, I’ve always sought to work at organizations that mirror that same sense of purpose — places with strong values and passionate people, much like the culture fostered on “the Hill.” Each of my career experiences has built upon the last, whether through taking on greater responsibility or exploring new projects that opened doors to my next opportunity. I’ve been fortunate to have incredible managers who invested in my growth and encouraged me to stretch further. The Holy Cross network runs deep — I always make it a point to connect with fellow Crusaders before joining a new company and after I arrive. Having that shared connection and support system has been invaluable throughout my career.

What has surprised you most about transitioning into a leadership role?

Two things stand out. First, I was surprised by the level of autonomy and decision-making authority that comes with leadership. It’s empowering but requires thoughtful, data-driven choices. I always aim to balance risk and reward, ensuring I can articulate the rationale behind each decision. Second, I’ve learned that great leaders operate with dynamic range — setting the high-level strategy while staying close to execution. I believe it’s essential to understand what your team is doing deeply, not just direct from above.

What is the most challenging aspect of your job? How do you navigate that challenge?

The most challenging aspects of my role are balancing competing priorities between teams and delivering an answer that may not be what others want to hear. I’ve learned that effective context setting is key — when people understand the “why” behind a decision, even tough messages can be received with trust and respect.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

I view leadership development as a continuous journey. Formal review cycles offer natural reflection points, but I also schedule regular development conversations with my manager to gather feedback and align on career goals. I actively seek input from direct reports and cross-functional partners to strengthen both my people leadership and influence across teams. Self-reflection helps me identify growth areas and ensure I’m showing up as the kind of leader I’d want to work for — intentional, open, and growth-oriented.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job?

Never stop learning. Build new skills and expand your toolkit — whether it’s AI fluency, negotiation skills, or effective communication. I recommend blending structured learning with on-the-job practice; the more “at bats” you get, the more natural those skills become. Above all, approach every task with optimism and a smile — even the unglamorous ones. When you take on work others avoid and do it with positivity, people remember. That mindset attracts opportunities, collaboration, and trust — often leading to your next great project, internal role or Promotion.

We know that relationships are important for any kind of development. How do you build and maintain your network?

I make it a point to connect with at least one new person each month, both inside and outside my company. I strive to learn about their career journey and what drives them. I set a calendar reminder to stay intentional and accountable, and I always connect with professionals on LinkedIn afterward. Expanding your LinkedIn network not only strengthens relationships but also helps tailor your feed and the opportunities you see to your career interests. I also respond to every outreach from a fellow Crusader, knowing the caliber of Holy Cross graduates and the shared foundation we have. Whenever possible, I look for ways to support their growth or make meaningful connections that can help them advance.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Mentors have been invaluable and true sounding boards for me. I recommend selecting someone that is outside of your direct management chain. I lean on them for perspective across all aspects of my career: reviewing project ideas, exploring next career opportunities, working through challenges, or celebrating wins. The best mentors are steady advisors in every season, who offer encouragement, perspective, and wisdom when it’s needed most.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

Network strategically and show genuine enthusiasm. When you land a conversation with someone from a company you are pursuing or a Crusader alumnus, come prepared with thoughtful questions, express your passion for the company, and demonstrate your commitment to the mission. Always follow-up with a Thank You note. Authentic curiosity, preparation and follow-up will leave a lasting impression.

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

Leverage the Holy Cross Alumni network and resources, there’s incredible content and programming available. Additionally, ask your network for recommendations of trusted advisors across areas like finance, wellness, and personal growth, and select those whose values align with your own. With so much information out there, limit your sources to one or two trusted experts per area to avoid overwhelm. Reassess regularly — if something isn’t serving you anymore, adjust. Building a fulfilling life after college is about intentional choices and ongoing alignment with your values.

Read More Leadership Spotlights.

Kristin Walker '10

Tell us about your job role and employer. What are you currently working on?

I’m the Senior Vice President of Merchandising at Tory Burch, based in New York City. My team and I are responsible for shaping the product strategy across categories—ensuring that what we bring to market reflects both the brand’s creative vision and our customer’s lifestyle.

Right now, we’re focused on refining how we infuse data-driven insights with our instinctive understanding of design and merchandising to build collections that feel both inspiring and trend-forward.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

Holy Cross played an enormous role in setting me on my career path. As an Economics and Art History major, I learned to think both analytically and creatively—skills that are at the heart of merchandising.

My first experience in fashion came through a Holy Cross connection: an internship at Marc Jacobs with alumna Carolyn Risoli ’86. That opportunity introduced me to the industry and showed me how powerful the Holy Cross network can be.

The liberal arts education also instilled curiosity, empathy, and the ability to see connections across disciplines—qualities that have guided me throughout my career.

What has surprised you most about transitioning into a leadership role?

The biggest surprise has been how much leadership is about listening. Early in your career, you’re focused on proving yourself and delivering results. As a leader, your success depends on empowering others—creating space for different voices, guiding decision-making, and helping people grow.

It’s less about having all the answers and more about asking the right questions.

What is the most challenging aspect of your job? How do you navigate that challenge?

Balancing creativity with commercial performance is a constant challenge in fashion. It’s easy to lean too far to one side or the other.

I navigate that by fostering open dialogue between our design, merchandising, and planning teams, ensuring every decision reflects both creative integrity and business strategy. It’s a balance of intuition and data, art and science—and that’s what keeps it interesting.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

I’ve found that leadership development is a lifelong process. I make time to learn from peers and mentors, to listen to my team’s feedback, and to regularly reflect on what’s working and what’s not.

Self-reflection helps me stay grounded—it reminds me to lead with empathy, stay curious, and evolve alongside the people I work with.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job?

Leadership isn’t tied to a title—it starts with how you show up every day. Be curious, collaborative, and kind. Take initiative, but also listen and learn from those around you.

The best leaders are constantly learning, and Holy Cross gives you a great foundation for that kind of growth mindset.

We know that relationships are important for any kind of development. How do you build and maintain your network?

I approach networking as relationship-building. I stay in touch with people I’ve worked with by checking in, celebrating their successes, and finding opportunities to collaborate or support them. I also make a point of mentoring younger colleagues—because so many people once did that for me. Authenticity and generosity go a long way.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Mentorship has been absolutely pivotal for me. My early mentors, including those I met through Holy Cross, taught me how to navigate challenges with confidence and integrity.

Now, I try to pay that forward by mentoring emerging talent. It’s incredibly rewarding to watch others grow and to know you’ve played a small part in their journey.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

Be proactive, persistent, and stay curious. The fashion industry moves quickly, but it’s also built on relationships and trust.

Gain experience wherever you can—internships, retail roles, or smaller brands—and use those opportunities to understand how the business really works. Lean into the Holy Cross network; it’s an extremely powerful resource.

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

Be intentional. It’s easy to get caught up in career momentum, but balance doesn’t happen by accident. Prioritize your well-being, nurture relationships, and set financial goals early.

The values that Holy Cross instills aren’t just professional assets; they’re essential to building a well-balanced and fulfilling life.

Read More Leadership Spotlights.

Zach Maybury '12

Tell us about your job role and employer. What are you currently working on?

I’m fortunate to work with some of the most talented people in the industry. My role is really about empowering the team to remove obstacles and create an environment that allows them to do their best work so we can accomplish our goals. This includes shaping our technology strategy, guiding organizational design, and continuing to build upon the amazing team at DraftKings. We have the exciting challenge of maintaining and evolving what I believe is the best platform in the industry. We’re constantly innovating, whether this is leveraging personalization, AI, or the next cutting edge technology to enhance our products, all while ensuring reliability, speed, and uptime in a rapidly paced environment that demands adaptability.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

My time at DraftKings has given me the opportunity to work for tremendous leaders who believed in my potential and consistently challenged me to take on more. Our industry is complex and fast-moving, and it’s those very challenges that have pushed me to grow—not just as a technologist, but as a leader and as a person. That growth ultimately led me to my role today as Chief Technology Officer. Looking back, my Holy Cross education played a foundational role in shaping how I navigate that complexity. The liberal arts environment encouraged me to think critically, communicate effectively, and approach problems from multiple perspectives, which are all skills that have proven invaluable in a technology-driven business. While my peers may have had more traditional technical training, my broad academic background combined with strong technical foundations has allowed me to bridge disciplines, collaborate across teams, and lead with both analytical rigor and empathy. Holy Cross prepared me to see connections across functions and people, which is a perspective that continues to guide me as I build teams at DraftKings.

What has surprised you most about transitioning into a leadership role?

What’s surprised me most about stepping into a leadership role is how often you’re faced with situations you’ve never encountered before. There’s no playbook, but with each new challenge, you begin to recognize common threads and learn to rely on judgement, critical thinking, and problem-solving to navigate through uncertainty. I’ve realized that sound judgment matters even more than I expected; leaders are often asked to make high-stakes decisions without complete information, and you have to get it right.

Leadership isn’t about telling people what to do—it’s about listening, creating space for new perspectives, and helping others unlock better ways to approach a problem. In this role, there really are no low-stakes decisions, so how you think, listen, and lead through ambiguity makes all the difference.

What is the most challenging aspect of your job? How do you navigate that challenge?

The most rewarding and simultaneously most challenging part of my job is bringing together a large, diverse group of individuals and getting everyone aligned around a common mission. When we launched our online sportsbook, for example, we were working with an enormous number of stakeholders—each with their own goals, opinions, and ambitions. Getting everyone on the same page required clarity, empathy, and a lot of communication.

Navigating that comes down to how feedback and direction flow through the organization. The way you communicate, such as ensuring that feedback both resonates and helps people grow, is just as important as shipping the next great product. Building alignment is an ongoing process of listening, translating vision into action, and reinforcing shared purpose.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

Self-reflection has been essential to my growth as a leader. As engineers, we’re wired to improve systems, and I try to apply that same mindset to myself when it comes to leadership—never fully satisfied, always learning. I coach my teams daily, but also work with my own mentors to challenge my perspective rather than just provide me with answers. In an industry that changes so quickly, it’s important to regularly reflect on how I lead and how our structure adapts to ensure we stay aligned as our environment evolves.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job?

Don’t be afraid to step well outside your comfort zone. Some of the best growth comes from taking on something completely new, such as when I began leading our Site Reliability Engineering team, which was an area I hadn’t worked in before. I had to quickly learn the domain, read everything I could, and lean on peers for insight while being open and humble about my knowledge gaps. The key is maintaining an open mind, a strong work ethic, and being willing to do the little things that move the team forward. Leadership isn’t about having all the answers, it’s about curiosity, effort, and commitment to helping your team succeed.

We know that relationships are important for any kind of development. How do you build and maintain your network?

Relationships are at the core of effective leadership. My impact isn’t delivered directly by me, but through the strength and trust within my management team. I focus on building relationships grounded in openness and radical candor where feedback flows honestly in both directions. When things go well, we celebrate together; when they don’t, we learn together. It’s a team sport, and maintaining those authentic, candid connections is what keeps the network strong and the organization growing.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

I’ve been fortunate to learn from incredible leaders, including past mentors and our former CTO, Travis, who continues to coach me today. I also still turn to my dad, another Holy Cross grad, for guidance. The common themes across those relationships are trust and honesty. The best mentors don’t sugarcoat; they tell you the hard truths and offer perspectives unclouded by emotion or organizational dynamics. Those conversations may not always change my ultimate decisions, but they help me think through different angles, anticipate outcomes, and approach challenges with greater clarity and confidence.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

My advice is to stay curious, adaptable, and hungry to learn. In our fast-moving, highly competitive industry, aptitude and a willingness to keep learning matter more than any specific skill set. New technologies—especially AI—are changing how we work, and being fluent or open to learning these skills is critical. But as the pace accelerates, sound judgment and strong systems thinking become even more important. There will be more opportunities to innovate, so the ability to think critically, adapt quickly, and make thoughtful decisions will set you apart.

What advice would you give to Holy Cross graduates about developing their personal life habits after college(finances, health, values, work/life balance)?

At Holy Cross, we often talked about being “men and women for others,” and that mindset has stayed with me. In my work, it shows up as a willingness to do whatever it takes to help the team win, believing that the sum is always greater than its parts. The same applies to my personal life: I try to live with purpose, give back through community and CSR efforts, and surround myself with good people. Good people make great teams and, ultimately, the best products. Finding that intersection between your personal values and your professional life is where the most meaningful growth happens. And as the demands of leadership increase, being supportive of others and truly present is just as important to long-term success as any performance metric.

Read More Leadership Spotlights.

Yarlennys Villaman Hale '14

Tell us about your role and employer. What are you currently working on?

I currently serve as the Director of Capital and Community Relations at the Massachusetts Bay Transportation Authority (MBTA), the oldest public transportation agency in the U.S. Our mission is to provide safe, reliable, and accessible transportation, and my work focuses on connecting the MBTA with the communities it serves, as well as with our more than 800,000 daily riders.

I lead the Public Engagement and Capital Engagement teams, driving initiatives that ensure both our riders and residents are informed, empowered, and able to provide meaningful input on the billions of dollars in capital projects across the system. By fostering strong community partnerships and strategically planning events and outreach, we create opportunities for the public to actively shape the future of transit in Massachusetts.

My vision is to make public engagement at the MBTA a model of transparency, collaboration, and impact—where every resident’s voice contributes to decisions that transform our transportation network and strengthen the communities it serves. At the same time, I work across departments to build cohesive, innovative projects that advance both capital development and community trust.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

I remember graduating from Holy Cross and thinking, “People say this degree will take me places, but I don’t know what’s next.” That uncertainty was scary. I reached out to the Holy Cross Alumni Office, which connected me with Trish Gannon, Class of 1987. At the time, she was working for the Boys & Girls Club of Boston. She took the time to meet with me, listened to what I enjoyed, and encouraged me to look into the MPA program at Suffolk University because it aligned with my goals. That conversation truly changed the course of my career.

I’ll never forget walking across the stage at my Suffolk graduation—Trish, who was serving on Suffolk’s Board of Trustees, stood up, and I gave her a big hug and said thank you. Moments like that remind me that life brings people into your path to guide you toward the purpose God has for you.

Through that journey, I began a career in public service at the state level. Along with my sister (Holy Cross ’15), I founded a 501(c)(3) nonprofit called Lazos Al Futuro in the Dominican Republic. Our mission is to support youth and help break barriers that might prevent students from finishing school. Today, we support 34 students, and 14 of them are attending top universities in the Dominican Republic.

All of these experiences—from Holy Cross to Suffolk, from mentors like Trish to launching my own nonprofit—remind me of the value of discernment at every stage of life. I’ve been fortunate to work in meaningful roles, and through it all, I try to live out the Holy Cross mission: to be a person for and with others.

What has surprised you most about transitioning into a leadership role?

Transitioning into a leadership role at the MBTA has been full of surprises. It’s such a busy agency, and learning a completely new field like transportation—with hundreds of acronyms and so many moving parts—can be overwhelming. Understanding how everything fits together takes time, but I’m determined to learn it all.

Starting a new job is always about taking baby steps, and as a working mom, it can feel like starting from scratch: learning a new field, meeting new colleagues, and finding my place. But every challenge has been a learning opportunity, and I’m excited for the growth that comes with it.

What is the most challenging aspect of your job? How do you navigate that challenge?

Working for the MBTA comes with its challenges—whether it’s community concerns about construction delays or complaints about how projects affect neighborhoods and daily rides. For me, the key is to take each challenge one step at a time and approach every situation with transparency and empathy.

Listening to people, acknowledging their concerns, and communicating honestly goes a long way in building trust and finding solutions that work for everyone. As our General Manager and Interim Secretary, Phil Eng, often reminds us, we want our riders to feel proud to ride—and we must ask ourselves how we meet the needs of today while building for the future.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

Right after college, I worked for a nonprofit supporting refugees and immigrants while completing my MPA in downtown Boston. I remember looking up at a tall building one day and visualizing myself working there—and not long after, I received an opportunity at the Attorney General’s Office, where I became the Director of Outreach. That role was a turning point for me. It made me realize that my education, experience, and perspective had real value—that I truly belonged in the room.

As a community organizer, I learned to meet people where they are and to think strategically about how to connect with different audiences. I led my first major initiative on Language Access, which was deeply personal to me as an immigrant from the Dominican Republic who once struggled with English. That project became a foundation for my leadership journey and shaped my future roles.

I’ve learned that leadership isn’t just about managing projects—it’s about being a team player, staying humble, and leading with empathy. Self-reflection has been essential. It reminds me of the Holy Cross motto: to be men and women for and with others. I try to live that out every day by treating people with respect, keeping my door open, and remembering where I came from.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers, industry, or job?

Don’t wait for opportunities to come to you—challenge yourself and take advantage of everything that comes your way. Whether it’s taking a leadership course, attending a conference, or simply getting to know the people you work with, every experience helps you grow.

Once you learn how to do your job, make your own mark so your work speaks for itself. It’s normal to have doubts or wonder “what if,” but in today’s world, you just have to take that first step and keep learning. Surround yourself with people who lift you up and who you can learn from. Little by little, you’ll climb higher—just remember to stay confident in who you are and never change what makes you, you.

We know that relationships are important for any kind of development. How do you build and maintain your network?

Relationships are everything. For me, building and maintaining my network often comes down to simple, genuine connections—grabbing coffee, making a quick call, or checking in. When I work in communities, I truly rely on those relationships.

I’m a bit old-fashioned: I love sending handwritten cards or thank-you emails to show appreciation. Your network and the people you surround yourself with help shape the leader you’re meant to be. In my line of work, reputation is everything, so I make a point of attending events and community meetings—but more importantly, I take the time to get to know people one-on-one.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

My mentors have truly changed my life. They’ve always pushed me to see more in myself, even when I couldn’t. Mentorship has helped me stay focused on what I want to do and where I want to go. I believe everyone needs a mentor at different stages in life—the guidance and encouragement make such a difference.

For me, mentoring others, especially Holy Cross students, is my way of giving back, just as my mentors did for me when I needed it most.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

If you’re interested in community engagement work, know that there are many paths you can take. Start exploring early—even volunteering for a local or statewide campaign can teach you a lot about working with people and seeing how communities come together.

If connecting with others excites you, there are meaningful opportunities in nonprofits, public service, and corporate roles that focus on community engagement, community affairs, or community relations. It’s impactful work, and every experience—big or small—helps you grow and make a real difference.

What advice would you give to Holy Cross graduates about developing personal life habits after college (finances, health, values, work/life balance)?

You’re still discovering who you are professionally, so challenge yourself while also taking care of yourself. Maintaining balance and caring for your mind and body is essential. For me, my faith moves mountains and reminds me to trust that God has a plan for me.

Since high school, I’ve written letters to myself at the end of each year to reflect on where I see myself and set goals for the future. Whether it’s journaling, going to the gym, or joining a group that aligns with your values, make space for what brings you happiness—don’t get lost in the busyness of life.

The second piece of advice is to never overlook the importance of spending time with friends and surrounding yourself with people who uplift you. Time is precious, and every moment matters when it comes to maintaining balance. Always remember: no matter where life takes you after Mount St. James, Holy Cross has your back. Don’t hesitate to ask for help when you need it. Life can feel like a rollercoaster, but you can rely on your Holy Cross network—a community that wants to see you thrive and will support you every step of the way.

Read More Leadership Spotlights.

Mike Flanagan '15

Tell us about your job role and employer. What are you currently working on?

I am a Director on the Business Transformation team at Envision Healthcare. My role focuses on executing innovative strategies that strengthen our core business functions and improve the experiences of both providers and patients.

I am currently leading the implementation of AI Ambient Scribe products across our provider group to reduce documentation burden, improve physician satisfaction, and increase productivity. In addition, I am overseeing the rollout of AI Autonomous Coding technology within our Revenue Cycle Management operations to enhance medical coding accuracy, efficiency, and downstream process performance.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

Growing up in a healthcare family—my father a urologist and my mother a nurse—the industry always felt like a natural fit. I saw firsthand the challenges clinicians face as they try to focus on patient care while navigating administrative, financial, and technological pressures.

During my time in consulting, I spent several years traveling the country, working with both large academic health systems and small community hospitals. Those experiences taught me how collaboration across clinicians, administrators, and support staff directly impacts the quality of care patients receive.

My Holy Cross education provided a diverse intellectual foundation that helped me transition from finance to healthcare consulting and ultimately into leadership within a large physician organization. The emphasis on critical thinking, ethical decision-making, and serving others continues to guide how I approach challenges and lead in the healthcare space.

What has surprised you most about transitioning into a leadership role?

What has surprised me most is how much the core skills I relied on early in my career still matter—maintaining a learning mindset, solving problems, collaborating, and leading with emotional intelligence. Even as the challenges become bigger and more complex, those same qualities continue to make a meaningful difference.

I’ve also seen how powerful it is to cultivate a team culture where people feel supported and heard. When everyone feels part of something bigger, the sense of camaraderie and shared purpose elevates the work.

What is the most challenging aspect of your job? How do you navigate that challenge?

One of the most challenging aspects of my job is navigating the ever-changing healthcare landscape. This includes balancing clinical staffing challenges, adapting to evolving government regulations, and keeping pace with rapid technological advancements.

To manage that complexity, I focus on staying closely connected to our clinical teams and understanding what truly makes their work easier and more meaningful. Listening to their feedback and keeping a pulse on broader market developments ensures that the solutions we implement genuinely improve both their day-to-day experience and patient care overall.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

I’ve learned that leadership development is an ongoing process—one that requires curiosity, humility, and a commitment to continuous learning. I actively seek out leadership development opportunities and make it a point to learn from others in the organization whose styles I admire. I try to identify qualities in great leaders that I can integrate into my own approach.

Self-reflection plays a major role in that process. Being honest about my strengths and areas for growth, seeking candid feedback, and viewing constructive criticism as an opportunity rather than a setback have all helped me grow. Leadership takes time to build, and patience—with yourself and with others—is essential along the way.

What advice would you give to Holy Cross young alumni about developing as leaders?

My biggest piece of advice is to lead with care and empathy. Set the tone by supporting those around you and helping create a positive, collaborative environment. Be a sponge around the leaders you admire and seek out mentors who can help you grow.

It’s also okay not to have all the answers. Some of the best leaders I’ve worked with are those who lean on others’ expertise and ask great questions. Above all, use emotional intelligence to understand how you can make your teammates’ lives a little easier. Leadership often starts with that simple act.

We know that relationships are important for any kind of development. How do you build and maintain your network?

Holy Cross has provided a remarkable network that has supported me at every stage of my career—whether applying for internships, landing my first job, exploring new opportunities, or offering guidance to fellow alumni and students. I make a point to stay connected with classmates and other Holy Cross graduates, celebrating their successes and learning about the work they’re doing.

I’ve also gained so much from colleagues across different phases of my career, from finance to healthcare consulting to my current role in strategy and transformation. Staying in touch with both current and former colleagues helps me learn from their experiences, understand the challenges they face, and find ways to support each other’s growth.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Throughout my career in healthcare, consulting, and finance, I’ve been fortunate to work with incredible individuals who have shaped how I think about growth and leadership. Many of my mentors stand out for their openness, honesty, and willingness to collaborate. I was drawn to them because of those qualities and learned a great deal—whether through their advice, their examples, or simply how they carried themselves during challenging situations.

Supporting mentees has become equally meaningful to me. I try to share the lessons I’ve learned to help colleagues and Holy Cross students or alumni navigate their own paths with confidence and perspective.

What advice would you give to Holy Cross young alumni interested in working in your industry?

For those interested in working in healthcare as a non-clinician, I encourage you to focus on how your work contributes to improving patient care and supporting those who provide it. Whether your role is in consulting, technology, operations, or finance, you can make a real impact on the patient experience and the overall delivery of care.

I’ve been fortunate to collaborate with physicians, nurses, and support staff and to spend countless hours in clinical settings, learning firsthand about the challenges they face each day.

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

Prioritizing your health, values, finances, work-life balance, and relationships with family and friends are essential. It can be difficult to juggle all these priorities, especially as you adjust to life after college and the start of your career. I’ve found that maintaining strength in each of these areas directly contributes to a better overall work experience and stronger performance. When work becomes challenging, you can lean on these foundations to keep you grounded. I encourage you to take care of both your physical and mental health, live by your core values in and outside of work, learn the basics of personal finance and begin saving and investing early, check in regularly on your work-life balance and recalibrate when needed, and stay connected to your support system of family and friends.

Read More Leadership Spotlights.

Brandon Cipolla '14

Tell us about your job role and employer. What are you currently working on?

I’m the VP of Account Management for North America at BitSight. Bitsight is the leading cyber risk intelligence platform used by more than 3,500 organizations to manage and reduce cyber risk across their own environments and third-party ecosystems. I lead three sales teams responsible for driving retention and revenue growth within our existing customer base. Right now, I’m focused on refining our go to market strategy and helping customers realize more value from BitSight’s expanding suite of products as the cyber risk landscape continues to evolve.

What key personal and/or career experiences led you to where you are today?  How did Holy Cross help shape those experiences? 

Playing baseball at Holy Cross shaped a lot of who I am today. Competing at the D1 level taught me discipline, resilience, coachability, and how to perform under pressure — all things that naturally led me into a career in sales. The competitiveness, need to bounce back quickly, team culture building, and the importance of preparation felt very similar to what I experienced on the field at Holy Cross. Being successful in sales demands many characteristics that high level athletes embody which is why it’s no mystery that many sales professionals have an athletic background.

What has surprised you most about transitioning into a leadership role? 

The biggest surprise for me was how different the definition of winning becomes. As an individual contributor in sales, you control your own destiny — hit your targets and you’ve most likely had a fantastic year. What I found in stepping into a leadership role — is that your ability to win is defined entirely by your team’s growth, execution, and mindset. It’s less about competing yourself and more about creating the environment where others can compete at a high level and succeed.

What is the most challenging aspect of your job? How do you navigate that challenge? 

The most challenging aspect of my job is leading a large sales organization through constant market change — increased competition, tighter budgets, and shifting customer priorities. As a leader, you have to keep the team focused, motivated, and confident even when the environment isn’t easy.

I navigate that by staying disciplined around fundamentals: clear messaging, commitment to process, and constant coaching. I also try to remove friction for the team to help them stay focused on the highest-impact activities. Most importantly, I stay close to customers and bring those insights back to the team so we’re always aligned with what the market actually needs. That combination helps us stay grounded and perform even in challenging conditions.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development? 

I continue to develop my leadership skills by investing heavily in coaching, feedback, and staying close to both my team members, executive leadership team, and the market. I regularly seek input from peers, mentors, and my direct reports to understand where I can improve. I also stay disciplined about learning — whether it’s studying top-performing teams, tapping into my network for informal catch ups, refining our sales process, or staying current on how buying behavior is changing in cybersecurity. There is endless content out there to learn from whether that is books/podcasts/YouTube, which I commit time to each week. Self-reflection plays a huge role. After major deals, tough conversations, or team challenges, I always take time to evaluate what I did well and what I could have done differently. It’s important to take time weekly/monthly/quarterly to look back and what worked and what didn’t. That reflection helps me adjust quickly, stay grounded, and lead with more clarity and consistency. It’s been one of the most important habits in my growth as a leader.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job? 

My advice to Holy Cross young alumni here is simple — don’t wait for a title to start leading. Leadership isn’t something magically gifted to you by a promotion or job description, it’s something you either practice every day or you don’t. You can lead from any seat in the workplace or in life by taking initiative, supporting others, solving problems instead of pointing to them, and carrying yourself with integrity and curiosity. A mistake I see often in early career professionals is assuming they need permission or a certain role to have influence or make decisions. The reality is people will notice your leadership long before you receive the title. 

The second piece of advice is to take risks early. There’s a balance between taking risks and playing reckless — but as a young alumni you have time on your side to make mistakes and learn. To become a great leader you have to learn how to be comfortable in uncomfortable situations. Try new things often — whether that’s in your role directly or something outside of your role that can help you gain experience and skillsets.

We know that relationships are important for any kind of development. How do you build and maintain your network?

I think about my network in three types of buckets. First, mentor relationships — people I can learn from, get coaching from, and go to for perspective, whether it’s about work or life. Second, my sales network — building relationships with talented people is essential when you’re leading teams and constantly recruiting top performers. And third, customers — the cybersecurity world is big, but it’s also incredibly interconnected. Staying close with customers, even as roles change, helps build long-term trust and keeps your network meaningful and active. The most important advice I can give on networking — whatever industry you’re in — is to start early and stay consistent. The work you need to put into developing your network takes time and won’t happen overnight. Many of your future career opportunities will be unlocked by strong relationships you develop in your network over time.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life? 

I’m fortunate to have had strong mentors throughout my career — and now, to mentor others as well. The role I’m in today came through a long-standing mentor relationship, which reinforced how valuable these connections can be. Because of that, I actively seek out new mentoring opportunities. I recently joined CareerSpring as an advisor, supporting First Generation, Lower Income students as they navigate their early careers. In the workplace, I dedicate a significant amount of time to coaching and developing the sellers on my team, and I stay connected with former team members to support their growth as they take on new challenges.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

In my opinion, tech sales is one of the best foundations you can have early in your career because it teaches you how companies actually operate. I used to think of it as getting my MBA without going to school — you work directly with cross-functional teams like product, engineering, customer success, legal, finance, and operations, and you learn how decisions get made and how businesses grow. Starting out in sales can give you an advantage, but I’ve also seen plenty of great sellers come from completely different backgrounds. And at the same time while you have the exposure to other teams, you can transition to other careers that may interest you.

If you’re interested in exploring tech sales, start with the Holy Cross network. Connect with alumni across different sectors of tech — I happen to be in cybersecurity, but there are so many categories that might spark your interest. What matters most is that you’re genuinely interested in what you’re selling and motivated to show up every day. The earning potential can be great, but if you don’t enjoy the work, burnout is real. Find a space that excites you, and the rest tends to fall into place. I’d be happy to connect with anyone looking to learn more. It’s a competitive market so any type of connection helps when trying to find your first start.

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

The saying “your 20s are for building the habits your 30s will thank you for” is spot on. For me, health and wellness became the foundation for showing up at my best in the workplace. Take the time to understand your personal “why” and what motivates you — that’s what will help you stay consistent with your routines. Your definition will look different from others’, but building habits that keep you sharp mentally and physically is essential. You’ll have learning moments along the way, so reflect often and adjust where needed. And through it all, maintain balance — work hard, but make sure you’re still enjoying your life outside of it.

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James Marino '14

Tell us about your job role and employer. What are you currently working on?

I’m a Senior Manager of Portfolio Management at the LEGO Group on the leadership team within our Commercial Analytics & Insights function. I stepped into the role earlier this year as a strategic thought partner to our VP, helping to shape our priorities, structure our work, and ensure we’re set up to deliver value across the commercial organization. The LEGO Group is a privately held company based in Billund, Denmark, still owned by the original Kristiansen family, and known globally for its iconic LEGO® bricks and play experiences.

My role spans strategy and planning, and I contribute across areas that shape direction, strengthen alignment, and enable our teams to deliver at scale. This includes shaping communication strategies, leading organizational assessments, and synthesizing insights into executive-level narratives. Right now, I’m focused on planning for the upcoming year and ensuring our strategic initiatives are positioned to drive revenue growth and support the company’s broader goals.

What key personal and/or career experiences led you to where you are today? How did Holy Cross help shape those experiences?

There are multiple personal and career experiences that have shaped my path. The most important, is my faith. It is the guiding principle that shapes how I live, lead, and serve others, both personally and professionally. My career has unfolded through that lens, along with a strong work ethic and a belief that every challenge presents an opportunity for growth. Throughout my journey, I have remained committed to excellence, driven by curiosity, and confident in stepping into new and uncertain spaces. Leading through ambiguity has become a defining part of my leadership approach.

My time at Bain & Company was instrumental in developing my strategic mindset. I learned to break down complexity, influence decision-making, and shape the direction of high-stakes work. Those skills have become foundational to the role I hold today.

Holy Cross laid the groundwork for my professional path. As an Economics major within a liberal arts curriculum, I learned to think critically, communicate clearly, and approach challenges from multiple perspectives. Together, all these experiences have shaped both my career and my leadership approach: thoughtful, people-centered, and focused on creating clarity and lasting impact.

What has surprised you most about transitioning into a leadership role?

One of the most surprising aspects of transitioning into a leadership role has been the number of escalations. I have realized that in many organizations, challenges are often pushed upward even when they could be resolved at the team level. I have learned to navigate these situations with a strategic mindset. Rather than immediately escalating an issue, I elevate problem-solving across the team by encouraging solution-oriented thinking before escalation. We consider our options, the recommendations we make, and how to move forward together as one team. This approach not only strengthens problem-solving at every level but also allows leadership to stay focused on the broader vision and make decisions that are more efficient, informed, and impactful.

What is the most challenging aspect of your job? How do you navigate that challenge?

One of the most challenging aspects of my role is staying centered and focused in a landscape filled with endless ideas and opportunities. It can be tempting to dive into every detail, but that approach is neither sustainable nor productive. I navigate this challenge by grounding my decisions in impact. I focus on which initiatives meaningfully advance our transformation, create value, or remove barriers for our teams. Using impact as a filter ensures we invest time and resources where they create the greatest value. It keeps me out of the weeds, supports clearer decision-making, and ensures we spend our energy where it matters most.

How do you continue to develop your leadership skills? What role has self- reflection played in your leadership development?

I approach leadership development as a continuous process. I intentionally seek opportunities that stretch my capabilities and prepare me to lead at the next level. Every experience teaches me something and helps me grow. Tactically, I invest in growth by continuously expanding my perspective through research, reading, and experimentation with new methodologies to stay current in both leadership and analytics. I am also fortunate to be part of the World 50 Group, which connects me with a global network of Chiefs of Staff and strategic operations leaders from Fortune 500 companies. Learning from peers in that community has been invaluable for broadening my perspective and challenging my assumptions. The LEGO Group places a strong emphasis on leadership development as well, and I will be participating in an upcoming leadership program designed to accelerate the growth of emerging leaders. Self-reflection also plays a central role in my development. I regularly step back to assess what worked, what did not, and how I can show up better for the team. Reflection keeps me grounded, helps me make more intentional decisions, and continually shapes me into the kind of leader I aspire to be.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job?

My biggest advice is to get involved and be willing to go the extra mile. Look for ways to elevate your team, strengthen collaboration, and introduce ideas that meaningfully move the organization forward. Small actions build trust, and trust is the foundation of leadership.

Invite challenges. One of the things I’ve carried with me comes from the Holy Cross seal—in hoc signo or “in this sign you will conquer” —is a belief that you can step into the unknown with confidence when you are grounded in your values and your faith. Every new role or opportunity will stretch you, and that’s where real growth happens. Trust yourself, trust what you have built, and lean into opportunities even when they feel bigger than you.

Leadership is not about having a title. It is about how you show up, how you treat others, and whether you take ownership to create an environment stronger than you found it. If you do those things consistently and with integrity, leadership will follow.

We know that relationships are important for any kind of development. How do you build and maintain your network?

Relationships are essential for both personal and professional growth, although they naturally evolve as life changes. I am married to my wonderful wife, Danielle, who is also a Holy Cross alum, and we have young boys. My network has shifted over time from college friendships to workplace connections to the community where we have chosen to raise our family.

What has remained constant is my genuine effort to connect with people.

One of the most valuable lessons I have carried with me from Dale Carnegie’s How to Win Friends and Influence People is to be sincerely interested in others and treat everyone with respect. Whether I’m meeting someone new or reconnecting with a fellow Crusader or work colleague, I focus on asking questions, listening well, and understanding their story. When you approach relationships with curiosity and care, not just an agenda, the connection becomes stronger, more authentic, and more lasting. That mindset has helped me build a diverse network over time and maintain relationships that enrich both my personal life and my career.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

I have been fortunate to have exceptional mentors throughout my career from HarbourVest Partners to Bain & Company to my work now at the LEGO Group. Each relationship taught me something different, and I approached all of them with the same mindset Holy Cross instilled in me: curiosity, humility, and a willingness to learn. I have come to understand that you do not need to have every answer. However, you do need to work hard, ask for help when you need it, and stay open to the wisdom of the people around you.

Mentorship has also shaped how I try to show up for others. My mentors modeled what it means to listen before speaking, to communicate with clarity and respect, and to serve the people you lead. Those lessons echo the Holy Cross tradition of forming people who lead through conscience and community. I carry that with me every day.

And while I have learned from many leaders, the most influential mentor in my life has always been my father. He built his first house at 16, and through his example I learned what hard work, faith, and integrity look like in practice. He taught me to deliver quality, stay grounded in my values, own my mistakes, and keep growing. His example, combined with the education and formation I received at Holy Cross, has had the greatest impact on both my career and my life.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

The LEGO Group is a company that genuinely cares about its customers, especially children and focuses on developing the best product for consumers. Our belief that “Children are our role models” and our mission to “Inspire and develop the builders of tomorrow” shape everything we do. We hold ourselves to a high standard with the philosophy “Only the best is good enough,” which means we are always looking for people who bring both their best work and their best selves. Roles here demand high standards and attract quality talent; we see hundreds or even thousands of applicants for many positions. The strongest candidates stand out by demonstrating not only expertise but also impact, such as how their work created real value for the people or communities they served. That mindset will feel familiar to Holy Cross alumni because it echoes the College’s emphasis on competence, compassion, and service for and with others. Experience in CPG or retail can help, but it is not required. What matters most is high quality thinking, curiosity, and a genuine passion for our mission. If you show that you care about the work, the consumer, and the craft, you will be a compelling candidate.

Finally, be open to working abroad. A global experience, whether in Europe or Asia can expand your perspective, strengthen your adaptability, and create new opportunities at the LEGO Group. In many ways, it reflects the Jesuit idea of being people “for and with others” on a broader, global scale.

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

My biggest advice is not to compare yourself to others. It’s especially difficult today, when social media makes it easy to see what people appear to be achieving. But if you stay rooted in gratitude—grateful for where you are, what you have, and who is in your life—it keeps you grounded. Everyone’s journey unfolds at a different pace and owning your individual path is the best way to build the future meant for you.

When you are calm, level-headed, and confident in your own direction, it naturally shapes the habits you form around finances, health, work/life balance, and the values you choose to live by. The faith tradition at Holy Cross teaches us to reflect, to discern, and to align our choices with what is good and meaningful. That framework has stayed with me long after graduation.

For me, I’ve centered my life around faith, family, and friends. When those remain at the core, the rest tends to fall into place in ways I could never have predicted. Staying grateful and making time for reflection helps me grow without feeling pressure to be perfect or measure my life against anyone else’s. Ultimately, my legacy is not defined by metrics or titles. It is defined by the values we uphold. For me, that is whether I align my mind with truth, my will with goodness, and my imagination with beauty—values that Holy Cross helped shape.

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Gina Righini Cipolla '15

Tell us about your job role and employer. What are you currently working on? 

I’m a Senior Marketing Manager at Verizon, where I manage creative strategy and campaign development for large-scale, 360° advertising campaigns — spanning TV, radio, digital, social, and more. My role sits at the intersection of creativity and strategy.

Right now, I’m managing our high-priority Holiday campaign. It’s one of our most robust campaigns and serves as a major business driver, so my focus is ensuring the creative is compelling and optimized to deliver strong results.

What key personal and/or career experiences led you to where you are today?  How did Holy Cross help shape those experiences? 

The summer before my senior year, I interned at one of the most iconic agencies— Ogilvy New York. I landed the opportunity through the Holy Cross Internship Program, powered by our incredibly strong alumni network.

That internship was my first real taste of advertising, and I was hooked from the start. It was competitive, fast-paced and exciting. While it was also filled with long nights, I learned more in those 10 weeks than I could have imagined. I gained exposure to the inner workings of account management, learned how to communicate effectively to different teams, and discovered the type of work that energized and inspired me.

Holy Cross played a major role in opening that door. Without the HC network, I’m not sure I would have gotten my foot into advertising — let alone in New York City. The critical thinking, writing, and people skills I developed at Holy Cross formed the foundation of how I show up in my career today.

What is the most challenging aspect of your job? How do you navigate that challenge?

One of the challenging aspects of my job is navigating the number of stakeholders involved in bringing a campaign to life. Each group — from internal partners to agency teams to senior leadership — brings a different perspective and objective. There’s rarely one “right” answer, so the challenge becomes shaping the creative in a way that aligns these viewpoints while still delivering the best work. It requires strategic thinking, clear communication, and confident presentation skills — but it’s a challenge I enjoy.

How do you continue to develop your leadership skills? What role has self-reflection played in your leadership development?

I grow my leadership skills in two ways: investing in learning and learning on the job.

• Investing in learning: I’ve participated in internal development programs at Verizon, including mentoring in the AdFellows program and completing a Pre-Leadership Program. Even when I’m nominated, I still try to raise my hand for new opportunities that stretch my comfort zone and help me grow both personally and professionally.
• Learning on the job: I actively ask for feedback, observe leaders I admire, and adopt the skills and behaviors that resonate. While I don’t currently manage a team, I make time to support and guide newer or less experienced teammates.

Self-reflection is also key. After big moments, I pause to consider what worked, what didn’t, and how I want to show up next time.

What advice would you give to Holy Cross young alumni about developing as leaders in their careers/industry/job?

Be a hand raiser. Reliability and eagerness go a long way — people trust those who show up.

Communicate well. Clear writing and presenting will set you apart early in your career.

Stay curious. Ask questions, listen, and understand both the big picture and the details.

Lead with kindness and confidence. Some of my most idolized leaders make people feel valued and supported. They model “we’re all in this together” and outline a clear plan on how we’re moving forward.

We know that relationships are important for any kind of development. How do you build and maintain your network?

I view networking as relationship-building. When people enjoy working with you and trust you when you are all “in the trenches”, they’ll think of you when opportunities arise.

To maintain my network, I:

• Make time for coffees, calls, and reconnecting
• Celebrate others’ wins
• Share opportunities when they’re a fit

People want to work with and help people who they have a genuine connection with. The strongest relationships grow from supporting and showing up for others.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Mentorship is impactful and rewarding – especially in an industry that can be ambiguous and fast-moving.

My mentors have:

• Given honest feedback on my strengths and areas for growth
• Pushed me to go for bigger opportunities
• Advocated for me in rooms I wasn’t in
• Modeled leadership traits I try to carry with me

I’ve also mentored junior team members, which is equally rewarding. It keeps me grounded, empathetic, and focused on how I can drive positive change for others and for the organization.

What advice would you give to Holy Cross young alumni who are interested in working in your industry?

Be eager and proactive. Soak in as much as you can. Do your own research. Reach out and ask questions if someone’s career path inspires you.

Lean into your network. Most opportunities come through people and the close relationships you build. Don’t be afraid to use it (this is something I still tell myself).

Sell yourself. Craft your experiences and how they can translate in a compelling way that shows strategic thinking and your personality. Passion projects, campus leadership, volunteer initiatives — it all counts. 

Dive into culture and creativity. Read, watch, scroll. The advertising landscape changes constantly. Make sure you’re in the know with the latest and have your own perspective on creativity. 

What advice would you give to Holy Cross graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

Give yourself time and grace — it’s not easy to figure out at first.

After college, I wanted to do it all: put in the hours at work to prove myself, maintain a daily workout routine like I had as a D1 athlete, and still have a full social life exploring a new city. I quickly realized that doing everything, and showing up as my best self across all wasn’t sustainable.

Burn-out is real and if you stretch yourself too thin, your lifestyle can start to become unhealthy. I eventually found a workout I genuinely enjoyed, which made fitness feel like a treat and not a chore. I prioritized friendships that are meaningful and long-lasting, and let go of the pressure to be everywhere socially.

Work/life balance is something I’m still working on — and likely always will be. Your priorities will shift as you move through different seasons of life, but put focus on making choices that align with your values and your well-being. Sometimes that’s setting aside time for a SoulCycle class, dinner with a friend, and sometimes it’s giving yourself time to rest (while watching Scandal reruns with your husband).

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