The Alexander Group

Category: Insights

I recently had the pleasure of attending the 28th Milken Institute Global Conference in Los Angeles. Although it ended last week, many insights have stayed with me. Over 900 speakers—global political leaders, business executives, scientists, non-profit leaders, and cultural and entertainment icons—participated in over 200 panels.

The speakers and subject matter were so informative, hopeful, and impactful that I want to share some of what I learned, especially about health and those who are making a difference.

An Impactful Welcome

Those attending conferences seldom remember the introductory welcome. This was not the case at the Milken Conference. After the standard welcome by Milken CEO Richard Ditizio, he went right to the bipartisan issue that concerns us all: the hostility with which people address those with different ideas and how that hostility bleeds across all areas of our society, impacting our children and often leading to violence.

Ditizio called on all of us to be willing to listen and learn from “those who don’t share your beliefs, celebrate the same holidays as you and love different people.” The Milken Conference is apolitical and always cordial, but Ditizio’s impactful words set an aspirational tone and were widely shared on social media. 

Health Matters

In an interview, Mehmet Oz, the TV personality known as “Dr. Oz” and now the Administrator of Medicare and Medicaid Services, spoke about his efforts to eliminate waste from our outdated reimbursement system.

He cited the fact that states have no way of knowing if a person moves from one state to another, which results in the federal government paying both states and costing taxpayers billions of dollars. Dr. Oz emphasized that every great nation takes care of its most vulnerable, and the most expensive thing we pay for is bad healthcare.

Women’s health was a subject of several sessions.

Former First Lady Jill Biden, chair of the Milken Institute’s newly established Women’s Health Network, spoke about pooling money from the private sector to finance historically underfunded women’s health research.

The sessions illuminated the telling statistics regarding women’s health. For example, Alzheimer’s affects women nearly twice as much as men, as do other diseases, to name a few: heart disease, autoimmune disease, osteoporosis, and stroke. Interestingly, many gynecologists receive little training regarding perimenopause and menopause.

Advances are being made in women’s health. Outside of the sessions, I met with an investor in Amboy Partners, a venture fund focused on women’s health, who spoke of a male birth control method—a cream—that is not that far off.

Longevity Session Offers Advice and Big News for Dog Owners

The session on longevity was standing room only and was one of my favorites—no doubt because of my age, although a number of Gen Xers were also in attendance. Each panelist was involved in some aspect of longevity: preventing Alzheimer’s, studying those who live to 100, which included an orthopedic surgeon/researcher and a researcher of longevity drugs.

Each of the panelists shared hacks for longevity:

  • In Sardinia, one key to living to 100 is having daughters.
  • Eat more of a plant-based diet and opt to eat at home
  • Know your numbers—blood pressure, blood sugar, cholesterol—and get tested regularly to forestall possible problems.
  • Bone health is a key to longevity, and it starts in childhood. Move, jump, and pound. Bones love to be bounced.
  • Exercise is the number one thing people can do to loosen up the toxic amyloid protein in the brain and maintain brain health, but exercise should be customized to the individual.

What Did We Learn? 

  • 93% of our lifespan is dependent on daily lifestyle choices. Evidence suggests that if we optimize all lifestyle factors, the average person could expect to live a healthy life to 90 or 95.  
  • A conservative estimate is that half of dementia cases may be preventable.
  • As belly fat gets larger, the memory size in the brain gets smaller. 
  • The biggest predictor of life expectancy is our zip code. 
  • Men lose their anabolic steroids in a linear fashion. With menopause, women have a mid-life cataclysmic event.
  • Only 2% of venture capital dollars are for women’s health after age 40. 
  • Women and men have different brains, and the most pivotal time for women is perimenopause transition.
  • 25% of women have a gene that is triggered at menopause.  Hormone therapy after menopause might take the woman with that gene off the road to dementia.
  • Studies have shown that if a patient spends 18 months at the Alzheimer’s Prevention Clinic following an aggressive prevention plan, Alzheimer’s could be delayed four to eight years. 

The “How” Behind Doing the Right Thing

Getting people to change their behaviors (diets and exercise) is hard. What we need to do is change our environment.  One hack to changing a population’s environment is to increase the walkability of a city or town.  If you live in a city like Houston, the average person walks about 4,000 steps a day, but if you live in a walkable city like Boulder, Colorado, or New York, you are likely to rack up closer to 10,000 steps a day.  For every daily 1,000-step increase, a person’s chance of dying reduces by 12 percent. A 40-year-old who adds an extra 5000 daily steps can extend their life expectancy by four to five years.

Getting to 100

Longevity is in the details. Women are five times more likely to reach 100 years old than men. However, only 20% of women who reach 100 will be in good shape, while 50% of men who reach 100 will be in good shape.  Living to be 100 should be the goal, even though we are not there today.  The current life expectancy for women who adhere to healthy lifestyles is 96, and for men it is 91. Life expectancy increases by two years every decade. Happiness increases as you age after traversing through middle age.

Challenges Ahead for Healthcare Advances

There are some potholes on the road to health and longevity. In the past five years, 98% of drugs approved by the U.S. Food and Drug Administration originated with National Institutes of Health grants. Experts at the Milken Global Conference said current funding cuts are expected to have long-lasting effects and possibly take years to reverse. Many up-and-coming scientists are leaving the U.S. in favor of countries more committed to research. 

One key to meeting the challenges lies in repositioning the health system toward being healthy instead of sick.

Some Dog Gone Good News

As an avid animal lover (especially of cats and dogs) I was intrigued and excited to learn about Loyal, a clinical-stage veterinary medicine company developing drugs intended to extend the health span and lifespan of dogs. Expect this drug to be approved in the next three years.

Philanthropy In Action

Philanthropy is a key emphasis at the Global Conference, and attendees are always delighted by ways to give back and the people leading those efforts.

Three of this year’s featured philanthropists were Patrick Dempsey (formerly of Grey’s Anatomy), Armando Christian Perez (Pitbull), and José Andrés (founder of World Central Kitchen). Pitbull spoke about a tuition-free public charter school network recognized globally as a leading education organization responsible for serving over 10,000 students. He stated, “it all started when a teacher believed in me.”

Dempsey started the Dempsey Center in Portland, Maine, in response to his mother’s cancer journey. The center offers supplemental, holistic treatments to cancer patients, such as yoga, Reiki, acupuncture, and counseling. Although its brick-and-mortar facility is in Maine, its 35 programs reach 32 states and four countries.

World Central Kitchen Founder Jose Andres, recently awarded the Presidential Medal of Freedom, was interviewed by California First partner Jennifer Siebel Newsom and spoke about how sharing food, especially in a crisis, can be a powerful tool for good.

Andres spoke about how storytelling, through his videos of feeding those in need after catastrophic events, communicates the level of devastation and the hope found after a warm meal and the promise of a new day. He praised the volunteers working in real time to set up food trucks and outdoor restaurants, most recently during the California wildfires.

“We should be treating people in emergencies like they are coming to my best restaurant,” Andres said. Newsom commented, “food can be a tool for communities to heal.”  As I exited these sessions, I heard attendees discussing how they could share what they learned.

Final Thoughts: Milken Global Conference 2025

These are indeed uncertain times and there is much reason for angst, anxiety and even fear. The beauty of the Milken Global Conference is the confluence of ideas and perspectives and the desire to flourish—the theme of this year’s Global Conference.

The Milken Institute has posted many sessions on its website and social media channels.

I hope they will get the attention they deserve.

This Milken Institute Global Conference post originally ran May 9, 2018 as part of an annual blog series.

Last week, I attended the exclusive, invitation-only 21st annual Milken Global Conference at the Beverly Hilton Hotel—home of the Golden Globes. This year’s theme was “Navigating a World in Transition.” For three days, attendees heard 740 entertainment, Wall Street, philanthropic, economic, scientific and world political leaders address everything from longevity, philanthropy, gun violence, diversity, politics, investment in Africa … well, you get the idea.

Imagine a scene where guests from all over the world bask in the warm L.A. sunshine from outdoor lounges decorated with plush sofas, cushions monogrammed with the Milken Institute logo, and a jumbo TV screen live-streaming some of the panels, while enjoying plentiful food and drink and unlimited celebrity sightings. Security is tight, and a badge and scannable facial ID are required for admittance. CNBC, Fox News, Facebook, and Bloomberg broadcast their morning programs in the lobby. And nearly 2,000 people move quickly from one session to the next. Fortune 500 CEOs, heads of state and celebrities all mingle without entourages, giving the event a certain buzzy vibe. Although the conference stated the dress code was business casual, most men wore suits, and women wore their best boardroom attire. 

Several people have asked me to share what I learned.

The most successful people in the world have a story. 

Because I’m in the people business, I’m always curious about what makes a great leader. What is their background? How did they get to where they are now? What were their challenges? How are they using their gifts? Here are four people who surprised, educated, and even inspired me about tough times, leadership, and impact. In a later blog, I will discuss other important discoveries and lessons.

“One has to help African people so they [can] help the animals” — Jane Goodall

Jane Goodall

Jane Goodall is a British primatologist and anthropologist who is the world’s foremost expert on chimpanzees. Goodall is best known for her more than 55-year study of social and family interactions of wild chimpanzees since she first went to Tanzania in 1960. She has worked extensively on conservation and animal welfare issues. At 84 years old, Goodall is charming and energetic, yet she projects a calm and Zen-like presence. Goodall gave much credit for her success to her mother, who “didn’t yell when I brought spiders to bed with me and who bought me books on animals.” Goodall said she realized from her work in Africa that one has to help African people so they could help the animals. “The most important thing we can give is hope. We can each make a difference every day and, in so doing, make the world a better place.”

Tom Brady

For you football fans, Brady plans to play for the Patriots next year and well into his forties. He respects coach Bill Belichick and acknowledges how much he has learned from him, although he admits Belichick is not easy to play for. And in the manner of a true politician, Brady danced around questions of why cornerback Malcolm Butler was benched—saying he didn’t realize he was benched until after the game and still didn’t know, which many of us found hard to believe.

Brady talked about how it “sucked” to lose the Super Bowl, and that after the game his three children were crying. He told them “Dad doesn’t win them all,” and taught them that part of life was learning to roll with disappointment. I found Brady to be most vulnerable and open when talking about his father, the most important influence in his life: “He taught me so much about working hard for his family—incredible determination, humility, and love—that’s what he was all about.”

Brady also gave some hints about his second career as a motivational coach, helping people in every career maximize their potential. “How can you, if you commit to the right things, be the best you can be?” he asked. And went on to say, “What I am learning as I get older is that it comes from within—joy, motivation, happiness—it comes from the inside.” He was quick to add that in the meantime he wants to “inspire people through his actions and performance.”

Alex Rodriguez

I wasn’t surprised to hear that legendary athlete Alex Rodriguez was speaking at the conference. After all, he is considered one of the greatest baseball players of all time, appears regularly on ESPN and Fox Sports, and has started A-Rod Corp, an integrated investment firm that manages internal and external capital. What did surprise me was the panel on which he participated (along with Kevin O’Leary of Shark Tank): “How to Be A Man in 2018”. The panel’s theme was how men are defining their roles in the march toward gender equality. I was surprised that a man whose success was earned through athletic prowess was so candid about what he considered greater measures of success, such as building great cultures and advocating equality and diversity. But one of the benefits of the Milken Global Conference is that you learn not to make snap judgments about people, and that every person can have a second act.

I was surprised that a man whose success was earned through athletic prowess was so candid about what he considered greater measures of success…

Rodriguez also talked about the influence his mother had on him—how she worked numerous jobs to enable him to pursue a baseball career—as well as the benefits of having strong women in his life including his daughters and “Jennifer” (a reference to current girlfriend Jennifer Lopez).

I was impressed that when talking about why some men take a long time to admit a mistake or vulnerability, he openly discussed his ban from baseball. He committed to apologize to everyone he had wronged and, even though it took him a long time, in doing so he learned the power of being forgiven and was able to use that time to turn inward.

George Takei

Attendees of the Milken Global Conference are encouraged to attend panels featuring ideas and people with whom they are not familiar. I had seen Star Trek many years ago, but it was not my thing, nor is the Howard Stern show where Takei is a regular guest. Takei appeared on a panel discussing the intersection of culture, art and politics.

Takei, a youthful-looking 81-year-old, opened by saying, “We live in a great country.” He then shared the emotional and captivating story of how he and his family were put under curfew, stripped of their bank accounts and then shipped off to a Japanese internment camp in Arkansas during World War II for no other reason than that they were of Japanese ancestry. “At five years old, I was labeled an enemy alien by my government … Yet, in one lifetime, because of the ideals of our democracy, I can sit here and discuss the intersection of culture and art and politics.”

“We as artists have a duty to use our sensitivity and creativity to reflect the time we live in.” — George Takei

Takei concluded by saying, “We as artists have a duty to use our sensitivity and creativity to reflect the time we live in.” The other panelists (actress Sophia Bush, playwright Sarah Gubbins, and screenwriter Damon Lindelof whose credits include “Lost” and “The Leftovers”) also shared how they chose or developed scripts that aligned with their core values, and how films and stories could change the world; but no one was impactful as Takei, who had suffered unspeakable cruelty yet so deeply loves his country. 

* photo credit: Milken Institute

Whether your organization is entering a phase of accelerated growth, preparing for a strategic exit, or solidifying leadership post-investment, identifying an exceptional sales leader is one of the most consequential decisions a company will make.

In my experience conducting searches for sales executives at privately held and investor-backed companies in the lower-middle market, I have witnessed firsthand the transformative impact of the right hire—and the significant cost of the wrong one.

When Founder-Led Sales Reaches Its Limits

In many emerging growth companies, the CEO, President, or founder often serves as the de facto head of sales. Early on, this dual role makes perfect sense. These leaders are frequently the company’s original and most effective salespeople, having built the business one relationship at a time. However, as the organization matures, this arrangement becomes unsustainable. Founders find themselves stretched thin, unable to focus on strategic initiatives as tactical demands consume their time. Without a shift in sales leadership, the company risks stalling just when it’s poised to scale.

The transition to a dedicated sales leader is a critical inflection point—and one that must be handled thoughtfully. A common misstep is promoting the top-performing salesperson into a leadership role. While individual contributors may excel at closing deals, sales leadership requires a distinct set of skills. High-performing sellers drive revenue; effective leaders build systems and teams that scale it. It is the difference between being a doer and becoming a multiplier.

What Sets Sales Leaders Apart in the Lower-Middle Market

Sales leadership in the lower-middle market bears little resemblance to that in large, publicly traded enterprises. Here, sales executives must be both visionary and hands-on. They often operate as both architect and executor, designing scalable systems while still engaging in frontline activities.

This hybrid, “player-coach” model is essential. The most effective leaders thrive in the field alongside their teams, guiding live deals, coaching in real time, and playing a pivotal role in onboarding and developing talent. They lead with humility and purpose, celebrating team success over individual accolades.

Builders First, Leaders Always

In many cases, the sales infrastructure in these companies is either underdeveloped or nonexistent. The outstanding sales leader enters ready to build—or refine—critical systems such as CRM platforms, pipeline definitions, performance metrics, and reliable forecasting mechanisms. They balance data-driven insights with qualitative input, building processes that evolve and scale with the business.

They also bring rigor to prospect prioritization and goal setting. Particularly in private equity-backed environments, these leaders understand how to deliver board-ready reporting, evaluate customer profitability, and focus the team on high-value opportunities. Their decision-making combines analytical precision with seasoned judgment, informed by prior experience in comparable settings.

A Strategic Connector, Not a Silo

Exceptional sales leaders understand that success is a cross-functional endeavor. They collaborate closely with marketing to align messaging and campaign strategy, even when marketing is outsourced. They maintain strong feedback loops with operations and product teams, ensuring promises made during the sales process align with delivery and that customer insights inform continuous improvement. In agile, fast-growing organizations, isolation is not an option.

Culture Begins with Leadership

In growth-stage companies, culture is not defined by mission statements, but by leadership’s behavior. The sales leader sets the tone through transparency, urgency, customer-centricity, and a relentless focus on outcomes. They create a high-performance environment where expectations are clear, accountability is built into the team’s rhythm, and wins are celebrated together.

The Power of Perspective

While internal promotions can be successful, many organizations benefit from fresh leadership, someone who has successfully scaled a sales function in a similar environment. These leaders bring a unique blend of entrepreneurial energy and operational discipline. They’ve seen what works, what doesn’t, and know how to execute with speed and intention.

The Right Sales Leader Doesn’t Just Fill a Role—They Redefine It

Companies in the midst of evolution, expansion, or preparing for a liquidity event should expect that the sales leader hired today will have an outsized impact on the company’s trajectory. These are leaders who architect systems, inspire performance, and scale with clarity and conviction.

The Alexander Group, recognized as one of the country’s top CEO executive search firms, presents “Five Questions With Extraordinary Leaders,” our interview series with visionary industry leaders. In this installment, Managing Director and Chief Client Officer Amanda K. Brady interviews Carly Caulfield, Race Director and General Manager of the Houston Marathon Committee, discussing management style, the evolution of the annual event, and the ephemeral nature of creating a marathon.

It’s not a stretch to describe Carly Caulfield’s career as a marathon, not a sprint.

As the longest-tenured Houston Marathon Committee employee on staff, Caulfield started with the organization at 19 years old, and over the next 25 years, the Chevron Houston Marathon grew to one of the nation’s premier multi-race running events.

She serves as Race Director and General Manager of the Houston Marathon Committee, an executive leadership role Caulfield knows from sneakers up.

Her early years with the marathon were lessons in on-the-spot training. She quickly ascended from office clerk to more senior roles and, in 2020, was promoted to her current position.

Caulfield is the marathon’s first female race director and won the Industry Leader Under 40 Award from the National Center for Sports Safety and Security (NCS4) in 2016. She currently serves on the NCS4 Advisory Committee. In June 2019, the world running Association of International Marathons and Distance Races (AIMS) named Caulfield as a founding member of the AIMS Sustainability Commission.

Caulfield earned a Bachelor of Business Administration from the University of Houston – Downtown and an Executive MBA program at the University of Houston’s Bauer College of Business.

Managing Director and Chief Client Officer Amanda K. Brady immediately knew Caulfield would be a perfect fit for our ongoing series “Five Questions With Extraordinary Leaders” because she’s seen firsthand how Caulfield leads before, during, and after the marathon.

Brady serves as Sector 4 Captain, enlisting and working with volunteers while coordinating with the Houston Police Department to keep runners, volunteers, and spectators safe throughout the race.

Read on to learn more about Caulfield, her mentors and how collaboration is key to achieving successful outcomes.

Q: You have been with the Houston Marathon for 25 years. How did you get into the marathon industry? 

A: By accident. I was a 19-year-old kid.  I was introduced to a board member of the Houston Marathon when they were looking for an office clerk; the job paid more than I was making at the time.  

I don’t recall wanting to pursue a specific career as a child, like a firefighter or a veterinarian. Around age 10 or 12, I read a book about a family with a lot of kids – I’m the oldest of six – and the parents were efficiency managers, and they practiced efficiency in their family. I read that book and thought, “That is what I want to be when I grow up, an efficiency manager.” I’m incredibly lucky to have fallen into this job, because every day I get to be the efficiency manager I dreamed of when I was a kid, and I love it.  

Q: How did you learn how to manage people? Were you trained, or did it come naturally? Has your management style changed over the last decade as the organization grew? 

 A: I wasn’t trained to manage people, and I don’t think it comes naturally, but I have learned a lot through experience and through making mistakes. I’m lucky in that when I was hired, we only had two employees. We used to be almost entirely volunteer-managed, with one employee to sell sponsorships and someone else – me – to answer the phone and man the fax machine. As volunteers stepped down or retired, I thought, “Oh, my gosh, I could do that.”  

First was registration, then volunteer coordinator, then charity coordinator. Eventually, it got to be too much. There’s only so many things you can do. I was 22 years old. I didn’t know you were allowed to ask for help, but I finally did. That is how the staff has grown over the years. I kept taking on a new job, and we kept hiring someone else to do the job I used to do.  

I’m incredibly lucky that no one has ever had my job before. So, no one ever says to me, “Well, Amanda used to do it that way.” No one’s ever done it before, and that’s an incredible source of freedom and power. I never had anyone to train me, but that also meant I had to learn many lessons the hard way. Maybe the first five or eight years, when we had emergencies – we still do –I got to swoop in and be a hero for those emergencies, and it felt great.  

Eventually, I matured or grew up enough to realize that was a ridiculous way to manage things. My greatest aspiration as the Race Director of the Houston Marathon is not to be needed, and it is what I ask of my team.  “You guys develop your teams enough so that if something happens to you, you get sick, get hit by a truck, you don’t need to be there,” that is my goal every year. I have a great team, and I’m proud that everyone on the OPS team has been around for more than five years. Many of them six or seven. 

My management style has certainly developed over the last 25 years. I believe in getting great people, giving them what they need, and then getting out of the way. That is my entire philosophy of management. And that comes from the fact that no one was in my way. I was making my own way.  

But I should add that the marathon community is an amazing community. There is no one I know in this industry that I can’t call and ask, “How do you deal with this? Will you loan me that? Can you send me this document?” It is amazingly collaborative. 
 

Q: You also manage a large group of volunteers. What are the challenges of managing such a large volunteer group, and how is that different from managing employees? 

 A: First, we couldn’t put on this event without our 5,000-plus volunteers. Volunteers have very different motivations from staff members. I love this event, but I also work to pay my mortgage. That’s not why our volunteers are part of the event, and I think volunteers, especially our Marathon Committee leadership, want to make a difference in the community. They want to solve problems. They want to feel valued. And it’s my and my team’s job to give volunteers the tools they need to feel that way.  

I don’t personally manage volunteers anymore. It is still my job to connect with our volunteers and make sure they have what they need to succeed in the important roles they play in the marathon’s success every year.  
 


From Left to Right:
Carly Caulfield, with her mom Mitzie Caulfield and sisters Bonnie and Betsy Caulfield, at the start of the Houston Marathon.

Q: Who are your mentors and guide stars?  Why them? 

A: First is my mom. My mom is a bad***.  She is a go-getter. I’m not a runner. But I understood running when my mom started running. She had never run a marathon, but she started training so she could go run “Carly’s Marathon.” She would talk to me every day about her training and that’s when I started to understand what it meant for people to train—putting in the miles, trying to avoid an injury, the nutrition, and just getting to the finish line. This is not a football game. You don’t buy a ticket to the marathon and attend it. It’s not about what you paid for your registration. It is about what you have paid in your life to get to this place. I didn’t understand that until my mom started running. But once she did, I understood that every marathoner and participant who called with a problem needed our attention. It was like solving problems for my mom. If my mom had a problem, I would go to the end of the earth to fix it. And we still do that. That is our guiding philosophy. We have rules. We can’t accommodate everything, but if we have made a mistake, we will fix it for you. I care so deeply about the participant experience because when I think about it, it’s my mom’s marathon. My family is out there running and volunteering. I hope that we treat every runner just like I would treat my family. 

The other person I would mention is Eric Berger with Space City Weather. He keeps us calm during weather emergencies. Their tagline is “no hype.” Just, “Here’s what’s happening. Here’s what we know. Here’s what we don’t know.” When I’m planning a marathon, I need to know what to expect, and Eric does that for me and many others across Houston. 

Q: What is the hardest part about serving as Race Director and General Manager of the Houston Marathon. Does any year stand out as particularly challenging, and if so, why? 

A: We are setting up for an event out of nothing in a few hours. You go to a football game in a stadium, you go to a show in the theater. Those are permanent venues. I think what’s unique about endurance sports is that we are building an entire event site out of thin air for just a moment. And then it goes away. So, every year has its unique challenges. Regardless of the challenges, our runners are investing their life in completing this event and we need to honor what these runners have invested in. 

As for a year that sticks out, I would mention two. The one that just happened in January 2025. I’m still really tired. There was a lot of stress and a lot of extra planning because of what happened in New Orleans on New Year’s Eve. 

Another was the Olympic trials in 2012. That definitely was a challenging year. Very proud of doing it. It was the first time the men and women had ever been hosted at the same time in the same place, and we went for it. We wanted to do something new and good for the sport and the city, and we did it.  

It was on Saturday morning before the marathon the next day. None of our signage was the same as the marathon signage. Everything had to be the Olympics and NBC and USATF. We set up the event, held the trials, and then we had to tear down that entire event across the city and, the next morning, stand up our normal marathon event with all those sponsors and that special signage. It was nuts. But it put Houston on the map for Elite Racing. “We had two American records here just this past January, and a history of record-breaking performances for many years. Our race is watched nationally and internationally, and that just wasn’t the case in 2000 when I started. We were just a local event with 7,000 runners, and now we are on the international stage with more than 35,000 runners.

This blog about professional beards was originally published in April 2015 and remains one of The Alexander Group’s most-read blogs.

Man touches his professional beard.

Professional beards are back and in a big way. The past few years have seen a significant upturn in the number of men wearing their facial hair “loud and proud,” both inside and outside of the office – a trend spanning industry, age, and even socioeconomic groups – leading to the inevitable question: “To beard or not to beard?”

Many of the world’s business leaders are sporting facial hair. Beards for professionals grace the faces of 

  • Sundar Pichai, CEO of Google and Alphabet
  • Reed Hastings, Co-founder and Executive Chairman of Netflix
  • Matt Parker, Executive Chairman of Nike
  • Dara Khosrowshahi, CEO of Uber
  • Larry Ellison, Co-founder, executive chairman, and CTO of Oracle
CEOs of 2025, each with a professional beard

The newspaper’s front page hasn’t been this hirsute since Carnegie, Rockefeller, Gould, Morgan, and other captains of industry were shaping the economy.

Captains of Industry with professional beards and facial hair

The Shaving Razor Market: Trends and Growth Outlook

The shaving razor industry has seen modest growth, with U.S. revenue reaching $2.9 billion in 2025 at a 1.0% CAGR. In Europe, the market is projected to hit $6.67 billion, growing 1.16% annually. While the industry declined around 2015, demand has stabilized as consumers embrace premium and sustainable grooming products.  

This shift reflects a broader trend—the changing role of facial hair in professional settings as beards become more accepted. Whether maintaining a beard or a clean shave, grooming choices now hold greater significance in personal and professional branding.

Professional Beards, Business, and Changing Perceptions

What has led to this dramatic change? Facial hair and capitalism have a connected history. Beards were once considered an indicator of liberal, anti-establishment views and dissident tendencies, championed by men like Karl Marx and Friedrich Engels, Che Guevara, and Fidel Castro.

However, not since the Robber Barons have professional beards been as popular in conservative, capitalist boardrooms as they are today. The hirsute look is currently not tied to any threatening economic or political ideology, and according to The New York Times, whiskers “no longer code as a threat.”

How Recession and Innovation Reshaped Grooming Trends

One interesting hypothesis is that many professionals began growing beards due to the recession of 2007-09. Christina Binkley of The Wall Street Journal describes two financial services professionals who lost their jobs and stopped shaving. She also points out that Al Gore grew a beard after losing the presidential election in 2000, stating that “it’s one of those tiny luxuries unleashed by unemployment.”

A significant contribution to the growing popularity of scruff comes from the technology industry.

The tech industry’s relaxed culture prioritizes innovation over strict dress codes, making facial hair widely accepted. Unlike traditional corporate environments, tech leaders are valued for their ideas rather than their grooming standards. This emphasis on creativity and individuality has helped normalize beards in professional settings.

The Alexander Group Managing Director John Lamar comments, “I went through a beard phase about 20 years ago. Okay, it was a goatee and not a very good one at that…I guess that was all I could muster.”

He continues, “I still like to go unshaven over the weekend…the rebel in me has not quite died. But come Monday morning, I break out the ol’ razor.” Lamar believes that the resurgence of professional beards has a lot to do with celebrities and techies. “The laid-back culture coupled with explosive wealth in these two worlds has created an “I just don’t care” attitude.”

According to a 2013 article in Daily Mail Reporter, men with beards “look as much as eight years older than their unshaven counterparts.” The late Steve Jobs of Apple is perhaps the epitome of how the image of the CEO has changed over the years.

In 2025, societal perceptions have evolved significantly. Beards have become mainstream and are widely accepted across various professional settings, reshaping perceptions of beards in the workplace. 

A notable example is the New York Yankees, who, in February 2025, lifted their 49-year-old ban on beards to align with modern grooming trends and appeal to a broader pool of talent. This shift reflects a broader cultural acceptance of facial hair, with beards now often seen as expressions of individuality and personal style rather than indicators of age or non-conformity.

Beard of Directors

Despite the growing popularity of professional beards for businessmen, the number of unshaven business executives remains relatively small.

The Alexander Group Managing Director Beth Ehrgott has only had one client with a beard in all her years of search, but says, “It seems strange to think that beards still seem out of place in corporate America, yet many companies all have diversity initiatives and programs.”

Sarah Mitchell, Associate Director in The Alexander Group’s San Francisco office, says there is so much facial hair in the Bay Area that “it’s more of the rule than the exception. But I suppose I don’t see it very much when I think about those working in a more conservative corporate environment, as opposed to Google or one of the many startups.”

While personal expression is valued in the Bay Area in 2025, men’s style has shifted, with both long professional beards and a clean shave being acceptable—as long as grooming remains intentional. The choice between maintaining facial hair or a clean shave depends on personal style and industry norms, but the emphasis is always on a neat and professional presentation.

Phillip Rudolph, the former Executive Vice President, Chief Legal & Risk Officer, and Corporate Secretary at Jack in the Box, was fully bearded in 2007 when he was interviewed and then hired at Jack in the Box. At the time, he did not believe beards “are even remotely disqualifying.”

However, before joining Jack in the Box, Rudolph was Vice President and Deputy General Counsel at McDonald’s. He explains that while interviewing for the position, the human resources executive “asked how attached I was to my beard. I noted to him that, more correctly put, the beard was attached to me.”

Rudolph continued, “But I took the hint and shaved off the beard. I remained clean-shaven throughout my five years with McDonald’s.” Perhaps geography plays a role. Jack in the Box is headquartered in San Diego, and McDonald’s home is in Chicago.

A recruiter for Shell Oil Company says that she rarely sees candidates with facial hair, and hirsute executives at Shell “are few and far between.”

A Hairy Decision on Professional Beards

The bottom line is that if you are going to go unshaven, there are certain written and unwritten rules to follow.

  • Know your company’s culture and whether or not there are regulations or unwritten “rules” concerning facial hair. Do your homework, or ask your manager.
  • If you are going to grow facial hair, make sure that it is trimmed and neat. The last thing any executive (perhaps outside of the creative arts) wants to see is something ill-groomed and distracting.
  • If you are interviewing, it is always better to play it safe. Research the industry and company. If in doubt, shave! You can always grow it back.
  • Finally, if you decide to grow facial hair, plan accordingly. Wait for a holiday or vacation for ample time for proper growth. Stubble tends to be perceived as sloppy or lazy.

John Lamar sums it up perfectly: “For me, it basically boils down to the corporate culture. There are places where ping-pong, beards, and tattoos are completely acceptable and places where they are not. Having interviewed thousands of executives in various corporate cultures, I subscribe to one simple rule regarding facial hair – just keep it neat and clean.”

“A big bushy beard that could potentially house a family of robins says to me you don’t care about your appearance or how others may perceive you. That doesn’t bode well for a future leader.”

Know Your Audience

The professional beard has evolved from a symbol of rebellion to an accepted, albeit still debated, element of executive style. While beards are more common in tech and creative industries, traditional corporate environments still lean toward a clean-shaven look. 

So, whether you prefer a clean-shaven look or professional men with beards aesthetic, understanding your industry’s expectations is key.

Whether interviewing for a new role or leading a boardroom, facial hair should align with your industry’s expectations and be well-maintained. 

If you’re navigating executive hiring decisions—or considering how personal presentation affects career progression—The Alexander Group can help. Our expertise in executive search ensures leaders are not just a cultural fit but a strategic asset to their organizations. Connect with us today to explore how we can help shape your leadership team for success.

Anyone who has ever been involved with a not-for-profit will at some point be asked to serve on a search committee or lead a search committee’s search for a new CEO/President or senior officer. We have written previously about the responsibilities of search committee members and how candidates can prepare for a search committee interview. Still, we wanted to take a deeper look at the role of the Search Committee Chair. We turn to Steve Taylor, a leader in the not-for-profit community for nearly 30 years, currently serving as Executive Vice President and Chief Mission Officer of the Arthritis Foundation. Steve recently chaired the search committee for the President & CEO of the National Health Council, which has been widely viewed as a well-run search with outstanding results. Below, Steve answers the questions we are frequently asked as not-for-profit recruits using search committees.

How big should a search committee be?

I believe the ideal size is seven, including the Chairman, who should also have a vote. You could do nine or five, but frankly, if the Committee becomes too large, it can be hard to coordinate schedules. There are too many opinions in the discussions, and you want every voice to be heard. You’ll also want to ensure it’s an odd number; that way, there is no tie.

Who should be on a search committee?

Much of it depends on the position. One to three members of the Executive Committee should be on the Search Committee and supplement that with volunteers who represent different parts of the organization. I recommend looking at the various responsibilities of the position you are trying to fill. Which volunteers can best represent and understand these responsibilities? The key to a successful search committee is to want members with different perspectives who live in various places. On the other hand, you don’t wish to search committee members being so free-spirited that they are substituting their vision for that of the Boards.

The ideal Search Committee member understands the organization’s history and future vision.

And that is so important when selecting volunteers to serve on a search committee: they need to be familiar [with], embrace the board’s vision for the organization, and represent different constituencies.

Should current employees sit on a search committee?

Many organizations wrestle with this question. Sometimes, it makes sense, especially when long-term employees understand the organization. But this is only a choice with challenges.

  • If there are internal candidates for the position, it can be challenging to ask a colleague [to] make an unbiased choice.
  • Secondly, a committee staff member may have a different strategic view of the organization than a high-ranking volunteer or board member.
  • Thirdly, it can be sensitive for an employee to be involved in salary discussions involving the successful candidate.

I typically recommend that one of the Search Committee members serve as a liaison to a group of employees or staff. In my recent search for the National Health Council, I led the search and maintained contact with the senior leadership team. While I did not discuss individual candidates, I asked the search firm for their opinions on the type of leaders we were seeking and communicated the progress of the search.

Who selects the search firm, and what should be considered?

I emphasize the importance of a strong partnership with the search firm. You want it to be a partnership, not just a firm presenting resumes. The chair should have meaningful input on selecting the search firm because they’ll be the one working [most] closely with them. Of course, the Search Committee reviews proposals and meets with several finalists. Ultimately, the Chair of the Search Committee should have a strong voice when selecting a search firm.

For me, it was critical that the search firm had experience organizing and administratively providing infrastructure to the Committee so that I and the Committee could focus on the candidates.

The chair should rely on something other than the Search Committee or search firm to coordinate all tasks. Sometimes, the chair must facilitate meetings or deal with scheduling or personnel challenges. The search firm should be willing to do more than search, as many search committee members have full-time jobs.

I advise my colleagues running search committees to be specific about what they want the search firm to do.

Do you want them to:

  • Attend search committee meetings?
  • Set the agenda for search committee meetings.
  • Provide interview questions.

It would be best to hire a search firm to do anything the Search Committee and its Chairman cannot or do not want to do due to time restraints.

It is a given that a search firm needs to have a robust Rolodex, but I’m still trying to figure out how to evaluate that. [laughing] You can determine recent searches a search firm has conducted for similar positions as we evaluated search firms, some listed searches that were conducted more than a decade ago! That was a lifetime ago in the not-for-profit world.

Finally, I believe you need to find a search firm that is upfront and honest with you about who the lead staff will be—and that you have the opportunity to meet with that lead staff to ensure compatibility and understanding of the process you envision—before you finalize your selection on a firm.

What allowances did you make during COVID-19 in the most recent search you chaired?

Overall, it worked out well. In specific ways, the process moved more efficiently, given that the Search Committee met via Zoom and the search firm, and we interviewed the candidates for first-round interviews via Zoom. One advantage we had as a search committee was that we all knew each other—some better than others—and this familiarity allowed us to work together well virtually.

Once we narrowed the process to our finalists, we asked them to meet face-to-face, socially distancing, wearing masks, etc., with another search committee member and me. Despite adapting to video conferencing, meeting the candidate personally makes a big difference. A candidate willing to invest the time to travel to a meeting and meet a group of people, some in person, some virtually, was critical to the final steps of our process.

We were able to observe how they handled themselves in the middle of a pandemic, watch how they coordinated their presentation, and even how they arranged the papers on the conference table. In a virtual interview, you have yet to learn if the candidate has sticky notes on their computer screen providing possible hints to questions. That was important to us because that’s what the job is going to be (ultimately):

  • Face-to-face meetings.
  • Working with different constituencies.
  • Being able to communicate and think on their feet.

Interestingly, we ended up with the same candidate if we had searched COVID.

As a search committee chair, how do you handle candidate withdrawals and surprises?

As a search committee chair or member, you understand that many candidates are currently in good positions, and you are hoping to attract them to your organization. You can’t get too nervous about that. It is part of the process. You reach for candidates; some attract, and some lose. And if a candidate pulls out, they should do it in the search process rather than later.

As for the second part of your question, as chair, you have to be flexible, responsive, and agile because issues arise that must be resolved quickly. Several times, I had to reach out to committee members individually to keep the process moving, either because a problem arose on a Friday night or because there was not enough time to call a full committee meeting. You establish that at the beginning of the search so there is a clear understanding. In every search, minor decisions may be made by the chair or by a smaller group on the Committee because trying to get everyone together all the time isn’t possible. Still, ultimately, the big decisions are made as a group.

How much time does it take to do a good job?

The time required ebbs and flows during the search. If you have a good search firm, as we did using The Alexander Group, there’s less time initially because you allow them to do the search and trust their judgment on the candidates they’re presenting. The search committee chair can focus on the higher-level items most important to finding the right candidate. Once the interview process is underway, you must be available for the search committee, search firm, [and] staff as the process unfolds. A significant time commitment is required from the chair. The organization needs someone who can commit time because you’ll never finish the search if it is not a priority.

Who should be the chair?

Choosing the right search committee chair is critical to a successful search. The chair needs to be a leader in the organization who understands its past and future vision. It does not have to be the current board chair. It could be a past board chair who might have more time because the position differs from the current board chair. It is essential that the chair can lead without supervision and is trusted by the board.

I don’t know whether to thank or ask him for my time and blissful ignorance.

Who do you ask?

I’m talking about the Chief Financial Officer candidate I worked with almost two years ago who said, “Oh, you have to be on TikTok to know where the world is headed.” This was the CFO of a $3 billion global organization. Indeed, he doesn’t have time to waste on an app that doesn’t add value to his life and career.

Off to TikTok I went, curious to see how it might reveal new executive hiring trends shaping the workforce.”

Embracing TikTok’s Influence on Executive Hiring Trends

I waded in the morass reluctantly at first. I thought of it as medicine I had to take if I believed the children were, in fact, our future. I’d scroll for ten minutes here and five minutes there. Yes, it was a lot of repetitive sound clips, dances, make-up tutorials, and University of Alabama first-year students showing their Outfit of The Day (OOTD, of course) as they rushed sororities (#bamatok in 2021. It was a magical time 🙄) 

My first impression was TikTok had little substance to offer to this (incredibly hip, vibrant, youthful) GenXer, but I admired these creators for putting themselves out there.

And then?

The algorithm started working.

When the Algorithm Gets It Right: A New Lens on Executive Hiring Trends

Before I knew it, I was fed applicable content from interior designers, immunologists and virologists, Diversity Equity and Inclusion warriors, registered dieticians, New York stage actors, human resources executives, physicians, and veterinarians. And a lot of beautiful and funny cats.

Have I been influenced? You could say so. I am typing this in my home office while strolling along on my new treadmill, which sits underneath my new standing desk. Thank you to the many 20-—and 30-somethings who showed me a day in their lives working for a Big Four/Big Law/FANG company from home with the treadmill setup.

I’m not here to tell you how you can get over 20,000 steps daily while feeling more energized, productive, and optimistic. But I wanted to share what I, a GenX executive search consultant, have gleaned from TikTok that is relevant, useful, and instructive to my career and outlook on business.

I scroll so you don’t have to. You’re welcome.

The Push for Salary Transparency

Hiring executives and those working in recruiting are aware of the new legislation in New York (and beyond) requiring employers to include a salary range, part of a broader move toward income transparency. 

It remains to be seen how effective and how much trouble these ranges will incite; we’ve seen executive search salaries range upwards of $500,000, which defeats the purpose of a range in the first place. 

That said, I have observed on this platform a significant push from Gen Z and Millennials to drop the veil on compensation, much as they push for transparency on all kinds of things that would make older generations blush. 

There are “man on the street” interviewers walking up to strangers on the street in busy metropolitan areas and asking, “How much do you make?” And people tell them! All kinds of corporate and non-corporate jobs. 

There are freshly resigned managers from well-known companies touting their employers when they post their roles with a lower salary range than what they paid them. 

There is a general, active push to normalize the salary conversation (just as they are normalizing what they weigh, how messy their house usually is, or their colostomy bag) to take out the mystique and power of those hiring. 

This active push raises the question: Is salary transparency a good thing for executive hiring trends and the broader workforce?” For organizations, it can promote trust and equity but also presents challenges in setting expectations.

Why This Matters to Executive Search

As salary transparency reshapes the hiring landscape, organizations face the dual challenge of meeting new legal requirements while aligning compensation with market expectations. 

The Alexander Group works closely with law firms and corporations to ensure their leadership hiring strategies incorporate fair and competitive compensation frameworks. This approach not only meets compliance but also attracts top-tier talent who value transparency and equity.

Okay, Boomer

A spotlight on just how different the generation’s approaches work. There’s a video trope in countless iterations poking fun at how different generations respond to all manner of workplace situations (i.e., how different generations handle a meeting being scheduled on a Friday afternoon, taking PTO, or the clock striking 5 pm). 

Suppose these “funny” videos are to be believed. In that case, Gen Z is only concerned about getting through today because the world is going up in flames anyway, so don’t expect them to work one molecule beyond their job description or schedule. 

Millennials are anxiety-ridden and people-pleasing, and Boomers love rules and how things have always been done. 

Amusingly, Gen X is more often than not entirely skipped over; we do not exist in the Gen Z content creator’s world. And because I am Gen X, I’m okay with that. I’ll figure it out on my own. I always have. 

While many of these videos are incredibly reductive (understatement), I do think that there is truth to be found in the “comedy”; with four generations working alongside one another, it is up to us to investigate what those differences in perspective are and how we can leverage them to be more successful together.

Why These Trends Matter for Leadership Hiring

The generational shifts and workplace trends discussed here aren’t just passing fads—they hold critical implications for executive hiring trends and leadership hiring. For corporate leaders and law firm executives, understanding these dynamics is essential to staying competitive.

For instance, salary transparency reflects a broader cultural demand for openness and trust, traits increasingly sought in leaders. Similarly, generational differences in workplace expectations highlight the need for executives who can bridge divides, foster collaboration, and drive results in a diverse workforce.

At The Alexander Group, we help our clients interpret and respond to these trends. Our expertise lies in identifying and recruiting leaders who embrace these shifts and align with your organization’s goals, ensuring long-term success in a rapidly changing workplace.

Recession or Not, We’re Battening Down the Hatches

I’ve witnessed a blossoming of “de-influencing” videos in the last two weeks. In contrast to the tried-and-true influencing content that tells me, either directly or covertly, that I must have an air fryer, a Gua Sha facial massager, a Stanley cup (not about hockey), or a standing desk with a treadmill underneath it, these videos go through lists of products that they have tried and are not worth your hard-earned dollars. 

We could also call these “honest product reviews,” but that wouldn’t be as catchy. From this trend, the economic contraction is being felt at a granular level, and there is pushback on consumerism from younger generations. 

I’ve also heard and seen a lot from trend forecasters on TikTok about “recession core” as an aesthetic becoming popular amongst the wealthy. It emphasizes dressing more simply, with less jewelry or expensive accessories, and more emphasis on functionality. 

Are these leading or trailing indicators of a dip in the economy? Time will tell, but it’s good to stay vigilant. Emerging executive hiring trends also reflect this economic uncertainty, highlighting the need for adaptable leaders. Organizations are increasingly seeking leaders who can navigate a leaner, more efficiency-focused landscape, aligning with this cultural pushback on consumerism.

Layoffs, Layoffs, Layoffs

Two or three weeks ago, if you were scrolling through TikTok, you could conclude that every tech employee in the US was being laid off. Reductions in force (RIFs) have been a fact of corporate life since the Dawn of Corporations, but in the past, they looked and felt more like faceless numbers in the headlines and a nebulous, encroaching sense of doom. 

This time, it feels different. With access to a tool like TikTok, the individuals affected can share their stories directly to the camera and access a limitless audience. Multiple videos have gone viral that show the actual layoff happening over Zoom; the more cold and heartless the dismissal, the more viral. 

From there, I’ve followed several laid-off tech employees as they share their “day in the life” videos, looking for their next job and trying to stay sane (or trying to go viral and not have to get another tech job.) The window this access has provided into the layoff and job search process has spawned, in turn, countless reaction videos and more profound thought into the waves of hiring and firing and what employers owe their employees. 

Again, transparency, enabled by new tools and direct access, will likely change the dynamics within the org chart.

Take all of this with a grain of salt

The double-edged sword of TikTok is the algorithm; it will get to know you quickly to a sometimes-spooky degree, but it can lead you to think that everyone out there is interested in and seeing the same things as you. I will tell you what that CFO did not:

  • Follow @veronicaandthebabyboo if you like cats.
  • Go forth; engage with a few opposing points of view.
  • Set a time limit.

Stay Ahead of the Executive Hiring Trends

Our workplaces are evolving faster than ever, shaped by digital platforms, generational shifts, and economic pressures, and staying ahead of these changes isn’t optional—it’s essential.

As executive hiring trends evolve, The Alexander Group serves as a strategic partner, helping organizations navigate shifting workplace dynamics, compensation, and leadership to secure executives who excel today and drive future success.

The Alexander Group specializes in C-level recruitment for boutique law firms, having conducted management searches since 1987. With unmatched experience in this space, we have worked longer and more successfully than any other executive search firm in the country. While we are best known for recruiting C-Suite leaders for AMLaw 100 firms, the fastest-growing segment of our law firm administrative practice is for firms with less than 300 attorneys.

Managing Director John Mann of The Alexander Group discusses C-Level Recruitment for Boutique Law Firms

John Mann’s Perspective on Boutique Law Firm Leadership Hiring

Managing Director John Mann has identified and recruited C-level leaders for regional and boutique law firms across the country for more than twenty years. We are proud of our impact in recruiting talent for these clients—talent that impacts a firm’s profitability, efficiency, and growth while contributing to a firm’s evolving culture.

John shares his expertise and perspective on the executive leadership recruiting process for law firms with fewer than 300 attorneys and the best boutique law firm leadership hiring practices.

Q: How does C-level recruitment for boutique law firms differ from an AMLaw 100 firm?

A: Many mid-size and boutique firms have been successful because of a practice area or their attorneys; however, some are not known for their operational efficiencies. Some of our clients have initially depended on their partners to manage non-legal areas of the firm.  At some point, it becomes untenable. Many of our law firm clients come to us because they have grown to the point where their chairman or managing partner can’t devote the time it takes to manage all the administrative and operational details of growing the firm.

We often recruit the firm’s first administrative executive leader. Sometimes, it is a chief financial officer, and other times, it is an executive director or chief operating officer. Regardless of the position, the goal is to allow lawyers to focus on building and maintaining client relationships—in short, to practice law.

Q: What influences a law firm to hire its first COO?

A: The significant change we often see is a newly elected managing partner or chairman succeeding a long-time managing partner. The newly elected managing partner/chairman would like to put their stamp on the role, focus more on strategy and growth, and have an experienced professional focus on support functions. Law firms that have dedicated functional leadership beyond the expertise of the executive committee/managing partner clearly have a competitive advantage.

Q: How do you recruit a COO or administrative leadership for your clients?

A: Every hire is important but none more so than a firm’s COO or administrative leader. Our clients trust us to get it right.  To do so, we spend time getting to know our clients and gain an understanding of their culture and what is important to them. We also work with clients to craft a go-to-market strategy.   Some firms seek to hire leaders to meet anticipated growth; others hire leaders to reduce costs and increase operating efficiencies. Some firms want a slate of candidates from outside the legal industry.  Every firm is different in their needs. 

We believe that not all potential candidates are found in a database.  We pair our robust database with the best research team in the business. This allows us to present a slate of candidates that meet our client’s needs, whether they are home to 30 lawyers or 300 lawyers.

Q: You mention that some law firms want to consider candidates outside the legal industry.  

What are examples of this? 

A: One of our clients is less than ten years old, yet they have established themselves as one of the nation’s largest specialty firms.  Over the last five years, the firm has retained us to staff their entire executive team. Some are seasoned law firm pros, yet their CFO came from a Fortune 500 retailer. A 100-attorney firm in Michigan retained us to recruit an entrepreneurial Chief Executive Officer who could think about ancillary practice areas. The success came from a global consumer products company.

Q: Does a firm’s location matter? 

Can a firm not based in a major metropolitan area recruit top talent? 

A: We have successfully recruited leadership throughout the United States. One thing the pandemic taught us is not all roads lead to major metropolitan cities.

We have recently completed searches including Portland, Maine, Cleveland, Ohio, Grand Rapids, Michigan, Indianapolis, Indiana, and Greenville, South Carolina.

About The Alexander Group

The Alexander Group excels in C-Level executive recruitment for law firms, offering tailored solutions that drive growth, efficiency, and cultural transformation. With decades of experience and a proven track record in identifying and securing top law firm COO and administrative leadership, we are the trusted partner for boutique and regional firms seeking to redefine their leadership and operational success.

The Alexander Group, recognized as one of the country’s top CEO executive search firms, presents “Five Questions With Extraordinary Leaders,” our interview series with visionary industry leaders. In this installment, Managing Director Sally King interviews Michael Caplan, COO of Lowenstein Sandler, discussing leadership style and advice for those seeking a Chief Operating Officer role at a large professional services or law firm.

Michael Caplan believes in diving in.

All in.

It’s how he connects with his team, peers, partners, and clients. Caplan is intentional about his leadership style, setting expectations and seeking growth opportunities. He interacts, listens, and strategizes with the goal of positively impacting his professional leadership team, attorneys, and firm.

With more than 30 years of experience in the accounting, financial, investment, and consulting industries and 20 years of corporate legal and law firm experience, Caplan takes a holistic approach to his role.

He combines his understanding of the business of law and his financial acumen with effective communication skills and a strategic approach to challenges.

Caplan joined Lowenstein Sandler in March 2024. A national law firm with over 350 lawyers based in New York, New Jersey, Palo Alto, Utah, and Washington, D.C., the firm represents leaders in virtually every sector of the global economy, particularly emphasizing investment funds, life sciences, and technology. It is recognized for its entrepreneurial spirit and high standard of client service.

Caplan believes Lowenstein is poised for exponential growth, and he is ready to lead the way.

Read on for Caplan’s “Five Questions With Extraordinary Leaders” conversation with King.

You recently joined Lowenstein but have served in this kind of role for over 10 years. How did you navigate your transition from Professional Services firms to law firms?

I’m a business-oriented COO, and I have a client’s perspective.  This approach has served me well in corporations across various sectors and serves me well as COO at Lowenstein.

Learning about law firm culture requires an understanding of practice groups, building relationships with partners, and how these elements work together in a competitive industry. But effectively leading any organization requires knowledge of basic business principles: What is

demand? What is productivity utilization? How should we think about our business differently? Why is revenue different from profit?

Additionally, I am very focused on how the law firm’s professional staff should be involved in client development, specifically in areas of operational expertise. I take these basic tenets and incorporate them into what I call “the business of law.” At Lowenstein, we have even branded these as “BEST—Business Enterprise Solutions Team.”

As a law firm COO, I work with both the attorneys and the business professionals who support them to facilitate the firm’s success. Internally, we are a team, and every participant understands their own value —what each of us brings to the firm. Externally, we need to differentiate ourselves from our competition in an increasingly competitive environment. One of the ways we do this is by helping clients with their operational effectiveness and operational excellence.

Lowenstein was looking for a leader on the business side who could help them think about how the firm can grow and adapt in the future —across different categories and different work streams. I am now part of the leadership team that is discussing and planning how to scale the firm. This was a big part of what attracted me to join Lowenstein.  After working in legal operations for two decades, this opportunity was more than being strategic.  It is leading-edge and innovative, and leading a team that can engage in driving revenue and the business is pretty cool. 

I relish having this seat at the table at Lowenstein, where the partners are eager to discuss best practices and growth strategies.

Recently, we’ve been focused on a strategic plan that leverages the business of law to serve our clients, our colleagues, and our communities.  We are looking at lateral partner hiring, innovative technology and solutions, data and business intelligence, cross-selling, conflicts, and lateral partner hiring, and we are looking at these elements in new ways. This approach will enable the firm to grow, be competitive, and STAY competitive— not only in our tier-one practices but how across all of our different groups from a cross-selling, collaborative perspective.

What have some of your biggest challenges been in law firms? Having 20/20 vision in hindsight, what might you change, and what might you do exactly the same? 

The role of a COO is different today than it was ten—even five years ago. A COO must communicate with partners so that the focus is on attracting profitable clients and efficiently running the business and practicing law. In addition to building a focus on lawyers, the firm must also invest in firm infrastructure and non-legal talent.

Today, we are seeing law firms that resist change.  The COO can play a big role here. Firms have to allow their COOs to have a voice, and partners with senior leadership need to promote and mandate that the COO have a voice. A strong COO with excellent communication skills can bring the partners in and drive change. On the other hand, if a firm has a COO unwilling to get out in front of a partnership that’s not letting the COO get out front, it will be ineffective in taking its law firm to the next level.

It is important for any COO to establish relationships with partners so that they feel heard.  Trust is very important. Once that is established, a COO can then effectively communicate to the partners how investing in the firm will help their practice. Any strategy will only be successful if the culture and partnership support it.

Currently, there is a highly competitive marketplace for clients and C-Suite leaders. I’m trying to hire chief officers, different levels of directors, and others within my professional staff with a strategic view of the business. Of course, every other law firm is seeking the same type of talent! However, Lowenstein Sandler offers an excellent proposition for highly qualified candidates because our firm truly values the opinions of its business strategists.

Now, looking back as an 11-year tenured COO of a law firm, I don’t get too bothered by the challenges that I faced earlier in my career. I’ve learned to take challenges in stride, reflect, and partner with other people to solve problems. I spend a lot of time with partners and our Chiefs brainstorming, strategizing and thinking about messaging and how to handle people challenges: how do we think holistically about where we want our teams to go and how do we get them there?

Running a law firm is not that difficult from an operational standpoint. But running a firm of partners and professional staff is the hardest part of the job. The people part of the job is challenging because you are literally managing “talent.” Every day can bring up new challenges from a people standpoint, but it is both challenging and invigorating as a leader.

What are some of the challenges you see on the horizon that you will need to address, and what is your game plan? 

AI presents an opportunity, but it’s a challenge. Where do we begin? How much data do we have? What is the data that the clients have? How are we thinking about our rate structures? How are we thinking about our hiring plans? How are we thinking about leveraging our profitability model? How are we getting in front of these communication plans with our clients?

AI presents a significant opportunity to engage clients, attorneys, and professional staff, but how do we address this? What comes first, second, third? Every vendor has a solution. I get 500 emails a day from unfamiliar vendors who want to solve all my problems.

Our chairman, Gary Wingens, and our full leadership and strategic planning committee are very focused on AI information and innovation. That is how we are managing this roadmap of products, data, communication, and client relationships as we guide our firm’s growth.

The other challenge is the growth of the lateral partner market. As a competitive national law firm, we want to grow our practices and become a destination firm for our key practices with lateral partners. But we are competing with many firms for the same lateral partner hires. The challenge is how we continue to be that destination firm and grow with the strategic plan of lateral partner hiring; as COO, I have to evaluate how to scale my teams to meet our projected growth.

If we hire 200 lawyers in the next two-and-a-half to three years, how many BD people do I need? What does practice management mean? How do we manage paralegals? How do we look at conflicts? How do I look at my recruiting team? How many billers and collectors do we need? Yet, at the same time, how do you manage the expense growth before the revenue comes in when you’re making partners so you continue to be very profitable?  This analysis requires a strategic view of how to manage the challenges of expense and investment, along with the revenue that will come in behind it.

What do you look for when hiring your chief team or people who will report to you, and how do you ensure you have a good mix of leadership attributes amongst your team?  What is your leadership and communication style? 

I believe that chief officers all need to have real leadership.  To me, this is table stakes. I operate as a COO, and I manage a team of people, but it’s a very flat organization. I love to embrace leaders and resources at all levels because I really try to truly create career aspirations for the folks who are on my teams. I want my teams to invest in their careers. It is not just about title and promotion, but there’s responsibility. Learn the firm, learn the partners, learn the practices, lead at every level. I’m really looking for people that are hungry, people that love to work, are excited and have ideas, and are not afraid to talk about them.

What advice would you give someone wanting to be a COO at a large professional services or law firm? How does Lowenstein manage succession for these roles, and how do you think other firms manage that process?

First of all, my advice to somebody who wants to be a COO is that you have to really invest in getting to know that firm. You have to truly take on the job as an owner.

I tell everybody whom I hire to take the first six months to a year and get to know people, build relationships, learn the firm, go on a listening tour, get on airplanes, go to different offices, make sure you work out a lot because you’re going to have a lot of meals and a lot of coffee, but listen and learn.   If you really truly want to be successful at the job of the COO, you have to build trust with your partners. And then you also have to build trust with your team under you, so that they will embrace you as the COO and keep you in the loop.

A reputation can be made or broken very quickly. You have to be willing to make those investments and sometimes sacrifices to be a very successful COO. The other piece of advice I would give is you’ve got to understand the financials. You have to truly get how the firm makes money, how we bill, how we collect, how we look at rates, how we price, what profitability means, what staffing and leverage utilization, productivity, demand go down the line, what is contribution? If you don’t understand the numbers of a law firm, it’s very hard to be a COO.

Leadership puzzle piece symbolizing the CIO role in law firms as a crucial element.
Leadership puzzle piece symbolizing the CIO role in law firms as a crucial element.

Historically, the CIO role in law firms has required an innovative strategist with an ironclad technology background to drive success. However, as law firms and client needs continue to evolve in the wake of artificial intelligence and client needs and expectations, so does the legal CIO role.

The Evolving Responsibilities of the CIO Role in Law Firms

A 2023 survey conducted by CIO Magazine reported that 47 percent of technology executives said security management and improving IT operations and systems performance were their top two responsibilities. Tasks such as business innovation, identifying competitive differentiation opportunities and business strategy were at the low end of the to-do list.

Fast-forward two years, and CIO feedback is changing along with expectations. CIO Magazine reports that the same technology leaders see driving business innovation as a top priority.

The surveyed CIOs said increased levels of business-focused strategic responsibilities will become part of their daily agenda, with technological emphasis being handed to other tech professionals within the firm.

It’s a sentiment echoed by The Alexander Group’s coterie of managing directors and directors, who have conducted dozens of CIO searches for law firm clients over the past four decades. We know the specific needs of law firm clients seeking forward-thinking CIOs who cover the tech infrastructure and bring leadership, communication, and innovative thinking to the table.

What will the expanded role of the law firm CIO look like in 2025, 2026, and beyond? Our team weighs in on this evolving role’s position requirements and responsibilities.

Insights from The Alexander Group on Law Firm CIOs

As the CIO role in law firms expands, so does the skill set required to excel. Today’s legal CIOs are expected to be more than just tech-savvy—they are strategic leaders, collaborators, and innovators. Here, The Alexander Group’s seasoned managing directors and directors share their perspectives on the essential qualities and evolving responsibilities that today’s top law firm CIOs must bring to the table.

“Today’s​ ​CIO​ ​possesses​ ​a​ ​combination​ ​of​ ​technical​ ​expertise​ ​and​ ​strategic​ ​leadership.​ ​They​ ​have​ ​become​ ​client-facing and ​ ​seek​ ways​ ​to​ ​enhance​ ​the​ ​client​ ​and​ ​lawyer/employee​experience.​ ​

Clients​ ​and​ ​lawyers​ ​are​ ​demanding​ ​innovative​ ​and​ ​cost-efficient​ ​technology​ ​solutions.​ ​​Artificial Intelligence continues​ ​to​ ​dominate​ ​potential​ ​technology​ ​solutions, and although it’s in​ ​its​ ​infancy,​ ​it​ ​will​ ​certainly​ ​increase​ ​and​ ​automate​ ​various​ ​billable​ ​activities. However,​ ​​it​ ​poses​ ​many​ ​challenges​ ​around​ ​ethics,​ ​security​, and​ ​compliance.”

John Lamar, Managing Director, The Alexander Group

“Just as law firm marketing has evolved into strategic business development, so has information technology. Now, stemming from IT roots, you will find chief innovation officers, chief security/data security officers, and chief knowledge management officers roles. All of these require an understanding of technology, both firm-side and that of their clients.

That said, IT infrastructure and support are table stakes. The CIO role and these newer, evolved roles begin with understanding business and client relationships, actively collaborating with clients, and finding ways to make those client relationships sticky.”

Amanda Brady, Managing Director/Chief Client Officer, The Alexander Group

“In the past, CIOs were primarily concerned with the network and infrastructure side of technology, but that has changed considerably. Many firms now understand the applications, various databases, and ease of use by all constituents is a much more valuable set of skills.

The amount of data collected by law firms is huge, and this, coupled with cross-level cyber security and AI, means that a top-flight CIO has to have extraordinary technical skills and understand what solutions may help lawyers in the practice of law and business professionals run the operations of the firm. 

The entire landscape is considerably more complex. An effective CIO must also be a strong teammate to other chiefs and an excellent manager of people who are perhaps not as blessed with good communication skills.”

Sally King, Managing Director, The Alexander Group

“The CIO role has been in the spotlight recently–from mitigating increased cyber-security threats and addressing client-driven information security requirements to shepherding and leading the migration to robust and reliable remote-work capabilities; to evaluating and deploying next-generation AI tools and pilot programs. And as a result, the level of institutional change management, business acumen, and firmwide strategic leadership skills have become equally important as technical expertise and operational know-how for top-tier CIOS.”

William Lepiesza, Director, The Alexander Group

“Law firms are increasingly hiring new CIOs. Historically, the IT function has been a critical operational function for law firms. The increasing demands on the technology function to be a driver of the business, as opposed to a supporter of the business, has led to a need for more business-savvy, forward-looking, strategic CIOs.  

The job description has evolved from infrastructure, software, and support aspects of the CIO role to a much greater emphasis on information security and technology innovation (including, but certainly not limited to, AI).

Many of our law firm clients have created separate, peer-level Chief Information Security Officer and Chief Innovation Officer roles to elevate those functions and work arm-in-arm with the more traditional CIO.”

Sarah Mitchell, Director, The Alexander Group

Essential Skills for a Forward-Thinking CIO

The law firm CIO role is evolving to become a top-to-bottom position emphasizing strong internal and external communication skills and the ability to be nimble in all aspects of the role. The CIO is a vital element of firm administrative leadership and will have the opportunity to contribute to a firm’s future in ways not previously imagined or expected.

Progress and innovation lie at the heart of technology, making this time in the CIO life cycle more dynamic and challenging than ever before and setting the stage for what’s next.

Visit our website for C-suite recruitment services tailored to law firm leadership and navigating the evolving CIO role in law firms.