From Waitressing to the C-Suite: Forbes Chief Sales and Marketing Officer Leann Bonanno Reflects on 17 Years and the Mentorship That Shaped Her Rise
“Tough moments in business are going to happen. But sometimes those moments are what lead to the strongest bonds. If you can find the positive or use it as a chance to connect, something good can come out of it.”
I had the pleasure of talking with Leann Bonanno. As the Chief Sales and Marketing Officer at Forbes, Leann has spent more than 17 years climbing the ranks of one of America’s most iconic business media brands. Raised in the small coastal town of Blue Point, New York, Bonanno credits her modest upbringing and early work ethic as the foundation for a career defined by persistence, adaptability, and relationship-driven leadership.
The middle child in a close-knit family, Bonanno grew up in Suffolk County on Long Island’s eastern shore. Sports were a formative part of her childhood, along with a sense of accountability developed through part-time jobs she held throughout high school and college. After graduating from James Madison University with a degree in marketing and business, Bonanno entered the workforce during the global financial crisis of 2007–2008. With few job prospects and a strong sense that the world had more to offer, she took her brother’s advice and traveled through Europe before returning home and applying, blindly, to a job opening at Forbes. She joined the company in 2008, beginning a journey that would span nearly two decades and see her take on key roles across marketing, branded content and global events.
At Forbes, Bonanno found a professional environment in flux. “When I started, Forbes magazine and Forbes.com were run independently,” she recalled. “The digital operations were in a completely different building.” As digital transformation swept the industry, she learned to navigate both traditional and emerging platforms, an agility that would shape her ascent through the organization.
In her early years, Bonanno worked in the marketing department before transitioning into sales, where she managed top accounts including technology companies and quickly gained a reputation for responsiveness and creative problem-solving. An early career misstep, pulling out a competitor’s phone during a client interaction, proved to be an unexpected breakthrough, leading to a stronger relationship and new opportunities. “Tough moments in business are going to happen,” she says. “But sometimes those moments are what lead to the strongest bonds.”
Over time, Bonanno became increasingly involved in Forbes’ LIVE events division, where she saw the potential to combine content, brand storytelling, and client engagement. By 2021, she was appointed Group Vice President of ForbesLive and Marketing, overseeing a global events portfolio that would expand to over 100 programs across six countries by 2024. Her leadership helped integrate data-driven marketing with high-touch event experiences, creating sponsorship models that were both measurable and compelling. Under her watch, the events business not only withstood the disruptions of the COVID-19 pandemic but emerged with stronger international reach and deeper editorial alignment.
Signature projects include the launch of a mentorship-focused women’s summit in the UAE, bringing together members of the Forbes 30 Under 30 and 50 Over 50 communities. The initiative, now entering its fifth year, has become a hallmark of Forbes’ efforts to support intergenerational dialogue and global networking among women leaders. Bonanno also champions integrated marketing campaigns that connect the full journey — from digital storytelling to live events and additional touchpoints helping clients build meaningful connections with audiences.
Her promotion in 2025 to Chief Sales and Marketing Officer marked a full-circle moment. In this expanded role, Bonanno now oversees revenue-facing functions at Forbes, including sales, marketing, and events. The elevation came amid a broader leadership realignment aimed at sharpening the company’s commercial strategy and accelerating diversification beyond traditional ad models.
Colleagues often describe Bonanno’s leadership style as pragmatic and people-oriented. With experience on both the creative and operational sides of the business, she’s known for bridging the gap between bold ideas and financial execution. Forbes CEO Sherry Phillips, herself a longtime mentor to Bonanno, cited her ability to “connect teams and drive results” as a key reason for the promotion.
Bonanno is candid about the challenges ahead. Like many media brands, Forbes is navigating a shifting technological and economic landscape. Artificial intelligence, evolving search engine dynamics, and consumer behavior changes have pushed the company to rethink how audiences find and engage with content. Bonanno now works closely with Forbes’ AI and Strategic Platforms group, led by Kyle Vinansky, to help future-proof its offerings, while also focusing on strengthening client relationships and expanding community-based experiences like the Under 30 Summit and ForbesBLK.
Bonanno’s approach to leadership is grounded in human connection. “At the end of the day, business is driven by people,” she says. “It’s about the relationships and connections you build. The more you connect, the more opportunities you create to bring people together and let them do their best work.” As she looks toward 2026, her goals center on team alignment, cross-functional collaboration, and staying true to the brand’s mission of championing success at every stage of life and business.
She credits much of her growth to the women who mentored her along the way, including Phillips, former Forbes executive Jessica Sibley (now CEO of TIME), and former colleagues who now hold leadership roles at The New York Times and other major outlets. Their confidence in her, she says, shaped her willingness to take on unfamiliar roles and grow through them. “They saw potential and trusted that I could take it on,” she reflects. “I hope to continue doing that for my team and future leaders.”
Yitzi: Leann, it’s a delight and an honor to meet you. Before we dive in deep, our readers would love to learn about your origin story, your personal origin story. Can you share with us the story of your childhood, how you grew up, and the seeds for all the great things that came afterward?
Leann: It’s so great to meet you. Absolutely. I grew up on the eastern shore of Long Island, in Suffolk County, in a small town called Blue Point. A beautiful town right on the water. I had a great upbringing and was always very close to my family. I have an older brother and younger sister.
I went down south for college, to James Madison University, where I studied marketing and business. At that time, not many people I knew went to JMU, but it has definitely grown in popularity. I had a great college experience.
I had a modest upbringing and always worked very hard and had jobs growing up. I worked in restaurants over the summers. During college, I worked at a local restaurant in town in Harrisonburg, and I also worked at the university recreation center, called UREC, in the marketing and design department.
I had a passion for sports having played many growing up as well as marketing. I was able to work at the local gym and support all the marketing campaigns to get people active and into the gym. I also supported their hiring campaigns which led me to pursue a career in business and marketing. I’ve always had a business performance mindset.
I graduated in 2007, which was right during the financial crisis. I had worked so hard, and it was a tough time. It was upsetting to think, “ I worked hard, got good grades, I went to a good college, and it’s still really hard to get a job.”
At that time, my brother said, “You really should travel. You’re going to work your whole life. Go see the world.” I took that advice, backpacked through Europe for a bit, came back, worked again at local restaurants to save money, and then I applied blind to Forbes. I didn’t know anyone there, went through a bunch of interviews, and here we are.
I started at Forbes in 2008, and I’ve been at Forbes my whole career. It’s been a long run. It’s definitely rare to be at the same company for so long.
There have been other opportunities that came my way, but Forbes is such a great company to work for. I’ve seen so much change and transformation over the years. When I started, Forbes magazine and Forbes.com were run independently, and the digital operations were in a completely different building. I had to walk up the street just to get to the digital team and learn about how we were transforming our business into the digital world.
So a lot has changed since then, but being a family-led company, it’s just been so great. I’ve worked for so many amazing leaders at Forbes. Anytime I considered venturing out, I’d be pulled back in with a new opportunity or a different role to take on.
Yitzi: Unbelievable. We’ll talk more about that in a minute. You probably have some amazing stories from different parts and stages of your career. Can you share with our readers one or two stories that stand out most in your mind?
Leann: Yes, I’m so grateful to have this role. I don’t know if you saw, but I’m just one month into my new job as Chief Sales and Marketing Officer. But I’ve been at the company for over 17 years.
Most recently, I was overseeing our marketing and global events team. I was always naturally drawn to the events side of the business, even when I was in sales, because that’s where you really build those amazing relationships with clients. You’re in the weeds together, doing the work.
I’ve had the great fortune of meeting so many amazing people through Forbes, which is always such a gift. One moment that really stands out was early in my sales career when I had the opportunity to attend one of our top events with one of our advertising partners. At the time, we had a partnership with NetJets, and we were doing a big event in Vegas hosted by Warren Buffett. I had the opportunity to meet him, and in the most gracious way, he gave me a kiss on the hand! That was definitely a highlight and a moment I will never forget meeting one of the greatest business leaders and investors of all time.
I’ve also met people like Sara Blakely and so many other incredible business leaders and celebrities.
We also host a big women’s conference every year in the Middle East, in the UAE. I had the opportunity to meet Gloria Steinem on the plane. It’s those kinds of moments where you have to pinch yourself and think, “Wow, what an amazing opportunity and job this is,” especially with the power Forbes has to bring such remarkable people together.
Yitzi: It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story about a funny mistake you made when you were first starting your career and the lesson you learned from it?
Leann: So many mistakes!
Well, here’s a funny one. I started my career in marketing at Forbes and worked in that department for about four or five years. But the majority of my career was on the sales team, where I was on the front lines with an account list, helping to drive revenue and grow the business.
I carried a lot of big technology accounts. I remember one time I was at an event, working on a partnership, and the CMO of a major company asked me to pull out my phone. He wanted to show me a new feature. I was young and didn’t quite understand where he was going with it. I pulled out my phone, and it was the competitor’s device.
He looked at me and said, “With all the business we give Forbes, you don’t have our product?” He was being sarcastic, but in that moment I froze. I was anxious. I hadn’t done anything wrong, but it felt like such a misstep. He was a CMO I had never been able to get a response from. After the event, I went and changed devices. I took a photo of his company’s ad in Forbes and sent it to him. From that point on, he responded to all my emails. It broke the ice and helped build that relationship.
The lesson I took from it is that tough moments in business are going to happen. But sometimes those moments are what lead to the strongest bonds. If you can find the positive or use it as a chance to connect, something good can come out of it. That’s just one example, but I always try to turn stressful or awkward moments into a way to build a more meaningful relationship.
Yitzi: It’s an amazing story and you’re an amazing storyteller. We love hearing stories where someone a bit further ahead opens a door or creates an opportunity that changes someone’s career trajectory. Do you have a story where you did that for someone else, or where someone did that for you?
Leann: I hope I can continue to do that for others. I’ve had such great mentors during my time at Forbes. As I mentioned, it’s a family-run company, and I’ve had the opportunity to work closely with Moira Forbes, who’s part of the Forbes family. I’ve worked for amazing female leaders at Forbes who saw something in me. Every time I got a new job opportunity, I might have questioned whether I was ready, but in all those moments, they believed in me.
Specifically, our current CEO, Sherry Phillips, I’ve worked with her for many years. She’s always supported my growth and has been an amazing mentor. She had a similar growth path, working on the revenue side, growing within the business, and eventually becoming CEO. My former boss, Jessica Sibley, is now the CEO of Time, and before that, I worked for the current CEO of The New York Times. All the women I’ve worked for throughout my career have become CEOs of major media companies, which is pretty incredible.
They’ve all been so supportive and gave me opportunities even when I might not have been fully ready. They saw potential and trusted that I could take it on. I hope to continue doing that for my team and future leaders, helping them grow. That’s the best part of the job. It’s a challenging environment we’re living in, but those are the best calls to make, when you get to support someone in their career and help them grow as a leader
Yitzi: So beautiful. What’s been the most challenging role or project you’ve taken on, and why?
Leann: There have been many, Yitzi. One thing I love about Forbes is that we move fast. We’re always testing and trying new things, and we try not to let internal hierarchy or red tape slow us down. I think that’s part of why we’ve been successful. But with that comes a lot of hard work.
Most recently, I’ve been overseeing our global events business. We do over 100 events a year, and we are lean and mighty. People are often surprised, when they really look under the hood, by how few people we have doing this on a global scale. It’s amazing.
One event that stands out is the one we host in the Middle East. It was a new idea where we bring together young women under 30 from the Forbes 30 Under 30 community and women over 50 who are achieving tremendous success later in life, and we create mentorship connections between them. The first year we did it was in 2022. We’re going into our fifth year now, but that first year was still during the tail end of COVID. You had to test negative to travel. We had COVID testing every day on site, and we were entering a new country. It was really hard, but also amazing, bringing together women from around the world to support each other.
It’s been incredible to see the team rally around that initiative, pull it off year after year, and bring new ideas to the table. That’s definitely been a proud accomplishment for me, and even more so for the team that helps build it.
Yitzi: Amazing. You mentioned the Forbes 30 Under 30 and the Forbes 50 Over 50. I remember before the 50 Over 50 came out, I was in a group of publicists, and people were saying how they felt bad that only young people could get this kind of recognition. They were like, “I wish there was something for people over 50.” And then you just came out with it, as if you’d heard their conversation. I’d love to hear the story behind that decision, because it really seems like it was a brilliant move. You’ve made so many people happy with it.
Leann: There are so many people beyond me at Forbes who helped conceive these ideas. Everything at Forbes is really anchored in our editorial and journalism, so I can’t take credit for the Forbes 30 Under 30 or the 50 Over 50 by any means. That’s really led by our editorial team and our Chief Content Officer, Randall Lane.
But it’s a concept that really ties into what Forbes is all about, bringing like-minded communities together and giving them the inspiration and tools they need to succeed in their careers, businesses, and personal lives. We’re known for our lists, and being recognized by Forbes means something. That’s helped grow our brand in a big way.
The concept of 50 Over 50 and 30 Under 30 is more about celebrating these communities. And it’s funny, because people assume it’s only for those exact age groups, but you’ll see people in their 40s at these events. It’s more about the spirit of it, recognizing people at different stages of their journeys.
We’ve got our big Under 30 Summit coming up in Ohio in a few weeks. We have a great partnership with JobsOhio, Ohio’s private nonprofit economic development Corporation, and we’re hosting it in Columbus. And again, it’s not just people under 30 who attend. It’s really about the mindset, whether you’re young, older, or somewhere in what people call the “messy middle,” you can chart your own path. There’s so much opportunity out there to be successful, to create, and to be inspired.
Yitzi: Beautiful. Let’s get to the centerpiece of our interview. You’re now one of the top leaders at Forbes. Tell us about the exciting new things you’re working on. Whatever you’re allowed to share, we’d love to hear. What can we hope to see in the future? What kind of fresh vitality or perspective are you hoping to bring?
Leann: As I mentioned, I’m just about one month into the job, but I’m really excited about the direction we’re headed. As you probably know, the industry is at a real inflection point. We’re facing challenges, but also exciting opportunities, especially with AI and the rapid pace of technological change.
My goal is to bring even more alignment across our teams. This role is a full-circle moment for me, since I’ve held positions in marketing, sales, and events. Now I get to lead all of those areas, and I have a deep understanding and empathy for the challenges each team faces.
There are incredibly talented people across the company, and my leadership style isn’t about micromanaging. It’s about figuring out what barriers I can help break down. I want to reduce silos and foster collaboration. One thing that’s always helped me grow in my career is building relationships, getting to know people across the company. The more you connect, the more opportunities you create to bring people together and let them do their best work.
Looking ahead to 2026, I’m focused on how we can continue to evolve. Last year, we won Adweek’s Experiential Brand of the Year for our events, which was a huge achievement. But we can’t rest on our success, we need to keep innovating and building. I’m excited about creating new products, launching new events, and also getting back to basics.
When I started at Forbes, we had a laser focus on our clients and relationships. In this new role, I want to bring that back to the forefront, because at the end of the day, business is driven by people. It’s about the relationships and connections you build. That’s where the real value is, and that’s what I’m most excited to focus on as we move into 2026.
Yitzi: You mentioned Forbes’s brand, and I think Forbes is singular, just having the Forbes gold seal, so to speak, is an incredible force multiplier. What can other brands do to emulate that? How do you get this gold-plated brand?
Leann: We have a very long-standing history at Forbes. We’ve built this brand over many years, but I think the reason it’s so strong is because we’ve always stayed true to our mission over the 100-plus years that Forbes has existed. We haven’t tried to cater to whatever trend is happening at the moment. At the end of the day, anywhere you go in the world, it’s about success.
Even when I first started working at Forbes, I remember how proud I was to tell my family and friends I got the job. I was so grateful to be able to work for a company like this. Whether you’re in Europe, the US, or anywhere else, it’s all about success.
It’s funny, we’ve been doing a lot of work with creators around the creator economy. We just held an event in Cannes earlier this year, and one of the creators who made the Forbes list said, “Now my parents think I have a real job because I’m in Forbes.” It just means so much to so many people.
That’s great, but there’s also a lot of competition. We can’t just stay comfortable and assume our brand will carry us forward. We have to continue to innovate, build new products, lean on technology, and keep the team motivated to grow and diversify the business.
I’m not sure I fully answered your question, but I’d say: stay true to your mission, your “why,” and to what you mean to people. Understand who your customers are and what they want, and that will help propel your brand forward.
Yitzi: You mentioned the challenges of AI. Can you be specific about what kind of challenges journalism is facing in general, and Forbes in particular? What kind of challenges does AI pose?
Leann: For the media industry, as you know, it’s really impacting search. Forbes has benefited for many years from ranking high in Google search, and that’s helped us scale our digital platform and our branded content offerings. We still reach nearly 150 million unique visitors a month.
So, the question is, how do we continue to leverage technology in a positive way? We actually have a new business unit at Forbes, the AI and Strategic Platforms group. It really comes down to how consumers are finding content online. It’s not a challenge unique to Forbes, it’s something the entire media industry is facing.
We have a lot of internal teams working hard to set us up for success in 2026. And while there are definitely challenges, there’s also a lot of opportunity. There are so many ways we can make our site more personalized, engage in audiences in new ways online, across our social platforms and within live event experiences. So, it’s also a really exciting time as we move forward.
Yitzi: As you know, probably since the advent of the smartphone, the floor has collapsed under newspapers and journalism. So many outlets have gone out of business, but outlets like Forbes and others have innovated and managed to stay ahead of the pack. What do you think other media outlets can do just to stay alive? Advertising in newspapers is basically gone. It used to be banner ads, and now those don’t bring in income. What are some ways they can find revenue?
Leann: I think for us, it’s really about the value you’re delivering to your audience. First and foremost, as I mentioned, everything we do starts with our editorial, really creating content in ways that make people feel Forbes is essential to their daily lives. They trust the brand to give them the information and tools they need to be successful.
We constantly have to work on making what we deliver valuable to our audience. Our product team and editorial team are always thinking about how we can strengthen that relationship, no matter where people are engaging with us. Our events business is also really strong. It helps us build communities where people come together and learn from each other.
So it’s the value to your audience, but also thinking about how to diversify your business. Our revenue model at Forbes isn’t just about advertising. The brand means so much in different ways. We have a strong e-commerce business. We also have what we call our accolades business, when companies or people are recognized on our lists, they can access badges, logos, and other tools to promote that recognition. It means something to be acknowledged by Forbes.
We have a lot of different ventures that help diversify revenue. But I think it starts with the brand, the relationship with your audience, and then the ability to scale in new ways. It’s about continuing to innovate and delivering more value to your clients and customers. How do you create real ROI for them? Marketers are under pressure to drive results and drive profitable business growth.. The demand for ROI just keeps getting stronger, especially with economic uncertainty.
Yitzi: So this is our signature question. Leann, you’ve been blessed with a lot of success, and you must have learned a lot from your experience. Can you share five things you’ve learned over the years that would’ve been really helpful to know when you first started? Five things you know now that you wish you knew at the beginning of your career.
Leann: Oh, that’s hard. Here’s what comes to mind.
- First, stay curious and keep learning. Always challenge yourself. It’s easy to fall into the day-to-day of your job and get comfortable, but stepping out of your comfort zone is so important. The things that scare you? You might not want to do them, but once you do, you feel so good and realize that is where real progress is. So pushing yourself in that way really matters.
- Second, relationships are key. It’s such an important part of growing in your career. And I think that’s even harder now for a lot of the younger workforce in a remote world. Business is really about people. The more we can connect on a human level, the stronger everything becomes.
- Third, as you grow in your career, don’t feel like you have to take everything on yourself. The real power is all about the team. Businesses are complex (certainly at Forbes), and it’s so important to get buy-in from the team and bring everyone together. I try to do that in my role. There are so many talented people across different functions, and getting everyone to the table is what really moves the business forward.
- Fourth, business is hard. The work we do can be intense, with long days. I started during the financial crisis. I took on the events role coming out of the pandemic. I’ve had to lead through times of real change. And I’ve learned that these tough moments are just that, moments. You take it day by day, and you get through it.
- And fifth, trust your gut. When you’re making decisions, especially under pressure, trust your instincts. They’ve usually led you to where you are for a reason.
Yitzi: Beautiful. So this is our final aspirational question. Leann, because of your amazing work and the platform you’ve built and helped build, you’re a person of enormous influence. If you could put out and spread an idea or inspire a movement that would bring the most good to the most people, what would that be?
Leann: I think at the end of the day, we’re all just people, right? People have different titles, some are in more senior roles, but behind the Zooms and the work meetings, everyone’s going through something, whether it’s good or bad. Life comes in seasons and chapters. I think it’s so important to always give people the benefit of the doubt because you never really know what someone might be dealing with.
That’s something I try to carry with me in both business and life: be kind. If someone’s having a bad day or a meeting didn’t go great, it’s easy to jump to a negative conclusion, but choosing to be optimistic and giving people grace makes a difference. You never know what’s going on behind the scenes, and bringing that kindness into everything we do is so important.
Yitzi: So beautiful. How can our readers continue to follow your work? And how can a large company that wants to become a client of Forbes get in touch with your team?
Leann: I’m still trying to balance doing my job and sharing the work on my social channels, which I need to get better at. But yes, definitely follow me on LinkedIn.
I really hope to share more of the great work the Forbes team is doing. Feryal is going to share my LinkedIn, but I do need to post more, Yitzi. Still, LinkedIn is probably the best place. We have such an incredibly talented team at Forbes. They deserve all the accolades and recognition. There are so many smart people behind the scenes who have supported my success and helped me step into this role. It’s truly a team effort.
And my Instagram? It’s mostly nieces, nephews, and family stuff, lots of babies, but I should start posting more about Forbes there too!
Yitzi: It’s truly been an honor and a joy to meet you. I hope we can stay connected, and I hope we do this again next year, when you become the CEO. You should have only blessings and good health.
Leann: Same to you, Yitzi. This was great. So nice to meet you. I’ll have to come see you in Baltimore one of these days. Or visit us in New York.
Yitzi: Yeah, I can’t wait.
Leann: Yitzi. Have a great day.
From Waitressing to the C-Suite: Forbes Chief Sales and Marketing Officer Leann Bonanno Reflects on… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.