Debbie Weiner: Championing Women's Success Through Support and Mentorship

One of Stifel's top-producing financial advisors, Debbie Weiner, started her career when women in finance were a rarity.? Now, she’s determined to open more doors for the next generation.

Debbie Weiner is a force of nature.? Not only is she one of Stifel’s top-producing financial advisors, but she has been recognized by Forbes as one of America’s Top Women Wealth Advisors (2020 and 2021) and Best-in-State Women Wealth Advisors (2022, 2023, and 2024) for New York.? On top of that, Debbie is a founding member of our Women’s Initiative Network (WIN), a group dedicated to empowering women to thrive both personally and professionally.

With over 40 years in the industry and $600 million in client assets under her belt, Debbie’s story is about dedication, leadership, and an unstoppable drive to succeed.? She’s not just a top advisor – she’s a mentor, a trailblazer, and an inspiration to many inside and outside of Stifel.

The Realities of Balancing a Demanding Career and a Family

In addition to being a top-producing financial advisor and advocate for women, Debbie is a caring mother and community leader.? So, she knows all too well the challenges of navigating personal and professional life demands.

“Anyone who works for a living, especially women, knows that there’s no such thing as work-life balance,” she says.? “If you want to be really successful and good at what you do, you pour yourself into it.”

For her, financial advising isn’t just a job.? It’s a calling.

“This isn’t a job where you clock in at 9 and out at 5.? It’s a business.? It’s an all-consuming career.”

Despite the long hours, Debbie has managed to thrive professionally and personally, thanks in part to a strong support system.? With an incredibly supportive husband, parents and in-laws who helped with school runs, and a reliable nanny, she was able to juggle her demanding career while raising a family.

As her daughter grew up, some of the daily demands eased, but Debbie still faces the challenge of carving out time for herself.

“I’m no longer responsible for anyone besides my elderly parents, but I still don’t take enough time off,” she admits.? “Once you’re successful, the pressure to maintain that success can be overwhelming, and burnout is a real risk.”

Even with a full schedule and responsibilities at home, Debbie never hesitated to take on volunteer leadership roles.

“I was passionate, and my husband supported me in pursuing those opportunities.? I wanted to be a role model for my child.”

Being involved in the community also had a professional upside.? It increased her visibility, opening doors to potential business opportunities.

“People saw me in leadership roles as a young mom and an investment advisor.? They told me, ‘I see how hard you work for the community, and I know you’ll bring that same dedication as a financial advisor.’”

Building Her Own Success at Stifel

She also credits Stifel for being an excellent partner.

“Stifel allows us to be entrepreneurial.? You make your own decisions here.? No one tells anyone what to do.”

This freedom has allowed Debbie to adapt her work over the years.

“As time passes, things change, whether that’s your personal life or relationship to the firm.? But one thing remains constant – management is there for me when I need them, and they give me the space to do my work independently.”

She also appreciates that the firm treats everyone equally.

“When you become a financial advisor, you free yourself from the limits of a salary,” she says.? “Your potential is unlimited, and the only cap is how hard you're willing to work.? Stifel has always provided the support and resources to make that a reality for everyone – men and women.”

Earning Respect as a Woman in Finance

Debbie didn’t always receive the respect she deserved in the industry.? “Men would occasionally call me ‘honey’ or ‘sweetie,’ and as challenging as it was, I made sure to be assertive,”? she says.? “I’d respond, ‘You can call me Debbie.? If you can’t remember that, call me Mrs. Weiner.’”

She also faced discrimination during numerous encounters over the years.

“I’d leave some meetings with industry professionals horrified by the disrespect I faced from people who asked inappropriate questions instead of treating me as a serious advisor,” she reflects.? “This was before anyone believed women belonged in finance.”

She quickly set them straight, challenging inappropriate questions and addressing condescending remarks like, “What about staying at home with your kids?” or enduring painfully aggressive handshakes.

“It was tough, but you have to hold your head high.? The best way to level the playing field is by excelling in business.? When you are successful, the critics have nothing left to say.”

Now, as a leader in the industry, Debbie makes it clear she won’t tolerate any form of discrimination.

“I tell women that I’m here to advocate for them.? If anyone gives you a hard time or makes you feel powerless, come to me, and I’ll stand up for you.”

From Isolation to Empowerment: Building a Strong Community for Women

Because Debbie began her career when few women were in the industry, she often found herself as the only female in the room.? Now, she makes it a priority to ensure others feel welcome and supported.

“At the WIN conference in Miami last year, I asked for a list of everyone attending from east of the Mississippi.? I personally called 25 women, many of whom I hadn’t met yet, and I told them, ‘You’re coming to Miami, and you might not know anyone yet, but you’ve got a friend in me.? I’ll introduce you to my friends from the Chairman’s Council.’”

And that commitment of supporting other women is a core part of Debbie’s approach at the firm.? After years of being one of the only women on the Chairman’s Council, she now makes it a point to reach out whenever another woman qualifies.

“I’ll call and say, ‘Hi, it’s Debbie Weiner.? You’re one of the few women on the Chairman’s Council, which means you’re part of our club.? You’ve got an instant group of friends, and we’ll go on the Chairman’s Council trip together.? If you want to join us for dinner, we’d love to have you.’”

Debbie believes that this welcoming spirit is shared among the women at Stifel.

“Women are very collaborative. When I get together with other female financial advisors, we can have fun and also talk about business.? We’re open about what we’re doing, how we’re doing it, and the challenges we’re facing.? Women are so generous with their time and their expertise.”

That spirit of generosity was also what led to the creation of WIN.

“I’m proud to have been part of the steering group that launched WIN,” she says.? “When we first realized we needed to create something, a small group of us stepped up and said, ‘We’ll make it happen.’? We gave it structure and life, and now it’s a nationally recognized entity that gives our firm credibility and helps us attract and retain top talent.”

Paving the Way for Future Generations

Having risen through the ranks without many female peers or a female mentor to guide her, Debbie knows firsthand the value of mentorship.? Although she had a supportive male branch manager, she understands the importance of having a female role model.? That’s one of the reasons she helped found WIN.

“We want this career to be accessible.? The next generation shouldn’t have to endure what we did. They shouldn’t be treated inappropriately or dismissed because of their gender.”

She embodies that collaborative and accessible approach to mentoring, never turning away a call and firmly rejecting the idea of gatekeeping.

“It’s not a zero-sum game.? Sharing knowledge, best practices, and insights won’t make me any less successful.”

And that’s not just lip service.

Debbie is in everyone's corner, whether she’s advising young women to negotiate for higher salaries, sharing her proven strategies with fellow financial advisors, or covering employee accounts.

“I’m a good coach and a good cheerleader.? I like empowering people, giving them the courage and tools they need to get what they deserve,” she says.? “At the end of the day, what does someone really need?? They need someone to believe in them, tell them they can do it, and show them what it takes to succeed.”

Debbie’s dedication to helping others also extends to her team.? Back in April, as a favor to one of her clients, she welcomed a young intern into her office to gain real-world experience in the industry.? Although Debbie’s schedule was packed, she personally covered the intern’s pay and ensured her team took the lead in providing guidance.? The experience involved meaningful projects, from investment research and number crunching to helping the team in any way she was asked.

“It’s about paying it forward,” she says.

Creating a Winning Career

We wrapped up our conversation with Debbie sharing a few pieces of advice.? First, she highlighted the importance of working for a firm that has your back.

“I encourage women who want a high-quality experience to find a place that fully supports you but also gives you the freedom to do what you do best,” she says.? “At Stifel, there’s unconditional support for the entrepreneurial spirit that is alive and well in every successful advisor – woman or man.? We get the tools and technology we need to excel without the burden of unnecessary layers of management.”

She also stressed the importance of taking risks and staying resilient to succeed.

“Many women are hardwired to be providers.? We want something guaranteed to support ourselves and our families.? But in a career like this, you have to take a leap of faith early on.? You have to say, ‘I’m giving up my salary, but I’m going to be successful, no matter what,’” she advises.? “As a woman, you may feel inclined to work twice as hard as everybody else, which means there’s little chance for work-life balance.? You need to be highly driven and willing to go all in.? But if you put in the effort, success will follow.? Your family will appreciate that you can be fulfilled both personally and professionally while providing financial security and a lasting legacy.

Forbes’ America’s Top Women Wealth Advisors and Best-in-State Women Wealth Advisors are based on the 12-month period ending September 30 of the year prior to publication and selected by SHOOK Research, LLC. Each are selected from a pool of nominations as indicated in the methodology. The rankings may not be representative of any one client’s experience and are not indicative of the financial advisor’s future performance. For more information, see www.stifel.info/award-disclosures .