Brown is also a marketer, has a proven background in insurance, and understands marketing and distribution, promotion and communications.

Not bad, for a working-class woman from Queens who made it her business to earn her success one step at a time.

Brown also has the distinction of being one of the right-hand people personally hired by her boss, Starr Companies Chairman and CEO—and insurance legend—Maurice R. Greenberg (to whom every single employee, including Brown, refers to as “Mr. Greenberg,” per his appropriate respect). One does not get selected for such a highly placed position for any reason other than that they are supremely qualified.

Brown, however, will have none of it when others refer to her as a person of great stature at the company. “I had a person recently say to me, 'I didn't realize that you were so important to the organization,' and I said, 'Why not? You are so important to the organization. Everyone here is important to the organization, so don't be confused about your role and why you're here.'”

When you have the skills, you can afford to not take yourself too seriously. “I've been called the 'marketing diva' for any number of reasons, including the fact that I walk proudly into the office in sunglasses. But the truth is that I'd like to think of myself as being accessible, and what you see is what you get.”

What you get, in Brown's case, is the brains behind the marketing and distribution for an insurance company that in the past several years has been stealthily gaining market share in such categories as Cyber, Energy and Construction, where a mix of technical expertise and robust client services are turning complex risks into opportunities.

As any top marketer would, Brown considers word choice carefully. “I think 'stealth' is a good word because it communicates movement and a leanness that even any of our predecessor companies, or my predecessor companies, would have liked to achieve around decision-making and execution,” she replies. “I like to think of us as being creative and flexible, and in some ways innovative—although sometimes that can be an overused word—with an eye toward meeting the current and the emerging needs of our customers and the brokers that serve them.”

In terms of the Starr brand becoming a household name in the insurance industry, says Brown, “we're not yet where we want to be, but we're not where we were. We're growing, there's a greater level of awareness of who we are. One of the things that's interesting about Starr is we have the DNA of a big company, but our competitive set might be different than some of those bigger players.” Brown sees her role as “keeper of the brand, and part of the brand is our people, our point of view, and our products, and pushing them out front, and so wanting to make sure that we do that in the right way,” she adds. “The best brands are the most authentic brands, whether it be people or companies, and they're consistent over time. There's no guessing.”

After four years with Starr, “I can look at the growth of our brand, and I'm so proud of what we've been able to accomplish,” she says. “But I think for us as a collective, it's never good enough, and we keep that single-mindedness around what's next. Let's keep going, what are we doing next? That presents its own challenges, which are exciting challenges as a person managing the brand.”

The Queen of Queens

Raised in Laurelton, Queens, Brown has never forsaken her roots; she brightens when asked where she grew up. “I'm very proud of my background,” she says. “My parents worked very hard to provide us everything that we needed and a few other things that we wanted, my sister and myself. It was a great upbringing.”

A self-described “public school kid,” Brown attended Benjamin Cardozo High School and credits her guidance counselor, Richard Kobliner (who has since passed) for setting her on the right career path.

“He took a special interest in me,” she says. “I'd already decided I would be going to SUNY Buffalo, because that's where my friends were going—I even had the sticker on the car. But I had a guardian angel who said, 'I see something special in you, and I want you to look at Middlebury College [in Vermont].' I'd never heard of it, and it literally changed the course of my life.”

Middlebury instilled in Brown a level of intellectual curiosity. “It was a safety net for experimentation,” she says. “It furthered my love of reading, and a liberal arts education, I think, is one of the best things that you can receive.

“He really opened a door for me,” she adds thoughtfully, about Kobliner. “He would say, 'It's my job to just kind of expose you and give you access, but you've done the heavy lifting, Leilani. You've done this. You could do that.' I miss him. Even after I started working he would call to check up on me, like, every six months. He would say, 'It's Richard, how are you?' And I would say, 'Mr. Kobliner?'”

For an alumni breakfast held during her senior year, Brown printed out 10 resumes, slipped them in oversized envelopes and handed them out. (“You couldn't miss them,” she laughs.) “I got four phone calls, one of them was from Chubb, and I went down for an interview.”

At Chubb, Brown earned her underwriting authority in a two-year training program in accident and health (which included on-the-job-training) that she completed in one year. “Sometimes, I'll get a call from colleagues who see my name in an old underwriting file,” she smiles. “It was a great experience, from a training perspective. They taught you underwriting skills and the language of the industry, and you learned the importance of relationship-building and consultative selling.” Underwriting accident and health coverages, she adds, taught her “how to be analytical, thoughtful, strategic, and think a little bit differently.

“We were really underwriting, and that intrigued me,” says Brown. She was assigned the Upstate New York territory and Puerto Rico, the latter because she is multilingual. “I have my credentialed academic Spanish, and here I am negotiating underwriting contracts with brokers in language, in Spanish, on the phone to Puerto Rico. So it was a fantastic experience.”

Years of varied experience followed, including positions as assistant vice president at NatWest bank; vice president/disability marketing at MetLife; and assistant vice president/marketing and VP/profit center executive at AIG, where she first encountered Mr. Greenberg.

Brown says one of her most notable career moments was when she received a shout-out from her boss on Starr's year-end company video. “That was a very proud moment for me,” she recalls. “Having that 'attagirl' from Mr. Greenberg, it doesn't get much better than that.”

'Lift as We Climb'

Brown is a firm believer in learning by doing, in putting yourself in the ring if you think you have what it takes to win.

“There are some people who would suggest that they have to check every single box on a list of 10 things that you need for the job before you can even raise your hand for it,” she says. “But if you're waiting to check every single box, you might count yourself out of the opportunity before you get a chance. Sometimes, some people see a readiness in you or a capability in you that you don't even see in yourself.”

That level of awareness includes encouraging talent in others regardless of gender, regardless of color. It's about recognizing one's ability to earn confidence in their skills and giving them a shot.

“Here's what I think, and hope,” she says. “It takes a lot of years of experience and accomplishments to get to the CEO and leadership chair. In order to do that, the [non-executive] level and the pipeline has to include women, for example, and others. Today, the 'working' level is definitely more balanced than the leadership level. My hope is that we will see a greater number of women emerging and ascending into the leadership ranks and the CEO ranks in the insurance industry.

“But in order for that to happen, those same people, those same others—whether it's women or people of color, etc.—need to have access to the projects, the opportunities that give them the accomplishments, so that they can ascend into those ranks. We have to create the environment for it to continue to move in that direction.

“It's up to us not only as women but also as insurance leaders to lift as we climb,” she adds. “We absolutely have to provide those opportunities, that mentorship, that feedback, that sponsorship in many cases to make sure that women and others are ascending into those ranks. Give them the opportunities, push them along, be the wind at their backs. Tell them, like someone told me, that they think you're capable beyond your own understanding of what your capabilities are.”

In an industry that has long been characterized as male, white and somewhat older, Brown's success is all the more special but simultaneously not at all surprising, given her capability and drive. For her, an uncompromising commitment to excellence has been the key: Put the work in, be true to yourself and others, own both your triumphs and your failures, and success—hopefully—will follow.

“My family and my circle of friends would always say that it is imperative that you work really hard and that the work is excellent,” she says. “That's the first step, and I think for me it's that work ethic. And for me, as a woman, as a woman of color, great work levels the playing field.

“Yes, there are always going to be headwinds. There's always going to be someone out there who assumes that you can do something or can't do something because of who you are or where you're from, or because you are whatever you are,” she adds. “But great work inoculates against some of those headwinds. You can't guarantee it, but great work and putting in the work and the experience inoculates against it.”

The 'Most Important Thing'

Brown is no stranger to striking a balance between responsibility to her work and her family, and emphasizes that her 12-year-old son is the most important thing in her life. “Capital letters, the Most Important Thing,” she says. “I had to have a conversation with my son a couple of years ago and I said, 'I need you to know that every single day I choose you. You are the most important thing, and I choose you every single day.' Now what that means is, I will try to make it to most things. I'm going to make it to many things, but there are going to be some things that I'm going to miss. But even when I'm not there, I'm still choosing you.”

That includes yielding the soccer games, for example, to her husband, Stanton, a former professional liability underwriter at Chubb and now an education strategy leader who just earned his doctorate in education from Fordham University. “Those are the times where I'll say, 'Dad is going to be there rooting you on,' or I've FaceTimed through my husband the soccer game at my desk.

“I don't do it alone,” she stresses. “I get a lot of help, whether it's family, friends, a wonderful babysitter, ordering groceries online and delegating things like that. I don't know that any of us are figuring it out perfectly. I have a quote somewhere on my refrigerator that says, 'You can have it all, but not at the same time.'”

That reality, says Brown, delivers some essential, realistic perspective for a working mom. “You can't win at everything, every single day,” she concedes. “There's a trade-off. I'll do a rock-solid performance, presentation or win or whatever it is, but that's also the day that I couldn't show up for something at home or forgot to do something at home that has a ripple effect. You do your best.

“Your family will keep it real for you, keep you really grounded in terms of your focus,” she adds. “When I walk in the door at night it's, 'Hey, what's for dinner?' And I'm like, 'What did you make?'”

Like it or not, any working person—at least, if they're honest with themselves—is always going to feel like they came up short either in their professional or personal life. Brown is no different.

“Hopefully on average it balances itself out, and I think that our work and family lives are converging in a unique way now—and we are bringing more of ourselves to work and we're talking openly about our kids and our families and our parents and our backdrops and our hobbies,” she says. “I think that makes for a richer work experience.”

The Chase is Wrong

Meanwhile, Brown remains committed to Starr and to giving credit—and advice—where it's due, especially to young talent.

“Sometimes I'm asked to sit on panels, and young people in particular will ask me, 'How do you move ahead?' I tell them, 'Don't chase a title. Chase the projects and the opportunities that give you the opportunity to claim an accomplishment.'”

Going back to marketing, she explains, “proof points” are required. “You need to be able to say, 'I did that for this company. I produced this result.' So it's really not about the title. If you can embrace that early in your career, I think you'll be far more satisfied.” That includes taking ownership of the work product, being enthusiastic about it, and standing behind it. “Then, it makes it easier to stand behind the mistakes when you do that—and there will be mistakes—and just work and give it your absolute best. Absolute best.

“I have a friend who gave me some great advice,” adds Brown. “He said to me, 'You have to let the game come to you.' We're often racing off to the next thing, but … now I'm just trying to be patient and reflective and let the game come to me.”