← The Top 5% Method®
The Top 5% Method®
The Playbook To Reach Fortune 500 Boards
00:34:25
In this episode of Driving Impact: The Top 5% Method, we sit down with Gail to unpack her journey from banking and retail to technology leadership - and ultimately to serving on the board of a $5B NASDAQ-listed company.
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- [00:00]
A
What's the biggest lie society tells us about success?
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B
There is a corporate ladder. There is not a straight line from entering your career to ending your career. It is a curly cue. It is a like a roller coaster of many twists and turns. And you know, for me, banking, retail, technology, board work, who knew? But it's not a straight line. And embrace the diversity in your own career.
- [00:48]
A
I'm so excited to welcome you to the podcast, the top 5% method. Welcome.
- [00:54]
B
Oh, I am so excited to be here. We've talked about this for a long time and I'm so excited about your podcast and I'm so happy to be a guest.
- [01:02]
A
I know, I know. And I think the topic of today is going to be so helpful because there's so many professionals who keep asking about how do we get, get to join a board? And I've been watching you for a while. We've worked together at LinkedIn and you have an amazing trajectory. And I thought I'm going to steal a little bit of our time to talk about your journey to a $5 billion in revenue, Nasdaq listed board. But before we jump in this hot topic, which is very important, I want us you to just tell us a little bit more about you, Gail, that we don't know.
- [01:37]
B
Okay, thank you. Thank you so much. I'll make this brief, but I think it's a good foundation. So I am from the Midwest and I had a very Midwestern kind of background. Two parents, both professionals, only child, but I. But I grew up watching TV with vision. And so there was a show called that Girl and it was starred by Marlo Thomas and she was a girl, working girl, career girl in Manhattan. And I was 10 years old and I said, I want to do that. And so that was kind of my north star for my life. So how did I make this actually happen? I went to Spelman College in Atlanta, which is a historically black college. I majored in economics, had a great background, and then was accepted out of Spelman into Harvard. Harvard Business School to do an mba. Yes, yes. It was a deferred admit, so I had to work for two years and I worked in banking. So I was a corporate banker, I worked on Wall street and I thought it was going to be one of those traditional folks. But I went back my second year and decided I took a retail course and I fell in love with retail and it's something that I've always loved and I wanted to do something in New York and it was perfect. And so I started my career in retail. With Bloomingdale's, I became a retail consultant, I worked for McKinsey and then that kind of snowballed into technology. Worked for Levi Strauss, other like big, big brands in the business. But there was this thing called E Commerce and E Commerce sort of turned into technology. So my first job was 25 years ago in working for Palm. And then I went to the big, big brand of SAP and technology and became a VP of marketing there. Interestingly enough, back in 2018, I worked in AI. I was the CMO of an AI company and supply chain and had a great experience. Series B startup, everybody should do it once or twice. It's a roller coaster. But it was a great thing.
- [03:53]
A
And experience I think is like, yeah, because like now it's 2025, almost 2026 and you were in AI before the, the big explosion of like chat, GPT, OpenAI and all of the other. And how, how do you look at the world now? Looking back at when you were the CMO of Noodle AI, it's, you know,
- [04:17]
B
although AI has become this larger than life technology, at the end of the day, it really is about providing value. And back in the day, 2018 to 2022, what we were all about was providing value and showing outsized results for our customers. So despite all AI hype, the talk today still is, is it providing value? Are projects generating revenue? Are people more productive? That's where we started. I think that's where it's all about. The good thing is people like me have no fear of this technology. It is not the big bad wolf. It's an avenue to gain more productivity and that's really all it is. So I feel like I've had a bit of a head start. And so When I joined LinkedIn and I led marketing for LinkedIn Sales Solutions, we were on the cusp of transitioning our product from where it was to being an AI first product. And so I've been doing this like for the last seven years and it's a ton of fun and it is going really interesting places. But what I'm doing now, because I've left LinkedIn, as have you, I think I have lots of wisdom to provide to others on adoption of AI, customer success with AI. Lots of things that people don't really talk about much. And so I'm setting myself up to advise companies, primarily startups, but also large cap companies, to talk about the AI revolution.
- [05:51]
A
I'm so excited and I'm excited about jumping on this topic, but also jumping about the topic of how do People access the elusive board service, but especially you on the board of Grocery Outlet, which is a $5 billion company and it's a retail company, which is so interesting. That's why I was smiling. Sometimes people see me smiling. Why is she smiling so much? Because I'm listen to your story of how you arrived to where you are and you thought you were going to be, you know, keep going in the banking way, but you fell in love with retail and then you ended up in the board of a $5 billion company that's NASDAQ listed as a board member. So a lot of people come to me in conversation, they're like, how do we access boards? So I want to hear about your journey of accessing this very highly ranked board. How did you do it? Was it a connection? Because people talk about it's who you know. Is that true?
- [06:48]
B
So I was headhunted onto the board of Grocery Outlet and that was when I was in the position of cmo. So one of the things that does tend to happen is board positions are correlated with C suite positions. And so because I was a chief marketing officer, I showed up on the radar of a search firm and we talked about my original love of retail, but also the supply chain AI experience I had, the SAP experience I had. And the board was at a sort of transition point where it wanted to diversify and add more women on the board. My God, it was a retailer of groceries and it didn't have any women on the board. And so I joined at a time. Within a two year period, four women were added to the board to diversify the voices around the table and get a little more focused on the consumer. So the magic here was that I was found, but that was because I had a public profile that I was active on LinkedIn, that people saw me speaking, they knew about my capabilities and my skills. And so I was fortunate enough to be brought into the fold of being a corporate board director through a search. Now I am thinking about expanding my corporate board service now. And so I'm taking a much more methodical approach, which I think we're going to get into in a minute, of how to expand that, how to leverage what I've done and how to prepare for boards.
- [08:20]
A
I think it's super interesting because people think about, and I'm talking to people, a lot of women ask about how do I get to this board. And people talk about age, people talk about tenure, but I think what one of the distinction is board, board ready versus executive ready. And I think it's Important, because you just said that once you became a CMO and you had the C suite title, that's when the headhunters suddenly started knocking at your door, number one. Secondly, you talked about the fact that you were vocal, so you had a personal brand and you were speaking in the landscape. So I want to hear a bit more from you about the difference between the resume or bio that landed you a CMO role and the resume or bio that landed you a board certificate seat.
- [09:02]
B
Yes, yes, that's really important. And that distinction and what you put on your resume and what you put in your board bio are completely different. So the board bio paints a picture of you as someone who can be in that executive conversation, advising the CEO as if you were he or she. And that's just such a different conversation. So in my current board bio, there's information on the rooms I've been in, the strategic transitions that I've been a part of, the technology transitions that I've been a part of. It talks about impact as opposed to saying I worked for SAP while at SAP, my impact on the business was that I launched the social channels and transitioned the marketing team from basically an analog to a digital channel. So it wants to hear about your impact. It also wants to hear about you as more of a well rounded person. What other boardrooms are you in? Now? This is a controversial point. I am on the board of two nonprofits and I would submit that although the work in a nonprofit is very different, the level of scrutiny, the fiduciary duty that you have is completely different. What is important is learning how to speak like a board member, being in the room with people who have been CEOs and other executives, and learning how to make your point, there are many people who come. So let me pause. I am a member of an organization called Black Women on Boards. I'm very happy to be a member of that organization, but what it teaches us is some of the tricks of the trade. And there is a gentleman who came to speak to us at a most recent event and he was talking about what it's like to be in the boardroom and how do you make your presence known. I think there is an analogy here to thinking about a resume versus a board bio. But he was explaining to us last week that when you think about how you comment within the boardroom, he says, be brief, be brilliant, and be gone. Right? So looking at 300 pages of information, assessing from all of that, where you think you can add your brilliance to the conversation, and then once you're in that conversation, make your point and get out because there's so much to be said, so much to be done and the CEO is dealing with, you know, all of the functions and all of the issues, especially dealing with the analysts in the street for a publicly held company that you really have to be brilliant and be brief. And so there's lots of tricks of the trade of being on a corporate board that people don't talk about much. But it's very subtle and it is a learned skill. I walked in, I didn't know anything about this. I had not taken any of the preparatory courses. Stanford has a directors college. I think Northwestern has something. Santa Clara College in the Bay Area has something. So lots of people take lots of courses to be prepared. I think those things are great for understanding governance. But. But what I would say is there's nothing like being in that room and understanding the dynamics and how you fit and how you're going to stand out.
- [12:34]
A
Yeah. So what you're speaking to is the experience of being on a board, whether it's a nonprofit board or publicly trade board is one of the best trainings. I would say that ideally you get your experience somewhere when you go on a publicly traded board because that, that would not be a good place to fail to learn. Right. To learn. Yeah. So let's talk a bit more about your first board strategy. So you rarely jump straight to a billion dollar public boards strategic first board for a person, should it be a nonprofit, an advisory board, a smaller private company? What would you advise, especially early career women who would like to target to gain some kind of foundational governance experience such that eventually they can add to their portfolio career this elusive Fortune 100 bard.
- [13:29]
B
There's two ways that I can answer that. Let me start this way by saying the trends in the marketplace now are such that gaining a board for a pre IPO companies. That's really where a lot of the action is right now and what a lot of people are looking at. Just know that the standards for governance and the structure of the committees might not be as well formed for a private company as it is for a public company. But what you will learn there and what you'll be able to talk about as you begin to have your board interviews is that you've had experience sitting alongside a CEO, a CRO, a CMO and advising them and generating results. And so that's really important because it gives you proof points. What it won't give you is all of the information that comes from being on the audit committee and so our auditors, for example Grocery outlet, are Deloitte. So sitting and making sure each month that our financial statements are in order, that they have audited our statements, that all of the risks in the business are well understood, that is a very different skill. And you typically wouldn't get that working as an advisor, as a board member of a smaller company. But I do think having that experience of being able to talk about sitting alongside a CEO is more easily gained from advising a pre IPO company. And so I'm, you know, I'm changing my tune from where I was maybe five years ago and saying that that is a perfect way in for the nonprofits. And lots of people ask me about this. Yeah, it's got to be the right nonprofit. There are many reasons to be on a nonprofit. And you know, with the state of the world today, being able to help underserved communities is really, really important. But on those boards, the benefit of doing it is also understanding who else is on the board and what they are able to do. Because typically nonprofit boards are pop regulated by people who have the time to do it. So they typically have been ex C suite executives, or they work for venture capital firms, or they work for private equity firms and they have additional cash to be philanthropists in their community. So you meet interesting people while you're doing this nonprofit board work. And so those connections are really, really important.
- [16:05]
A
Some people have said that a lot of the nonprofits you have to fundraise a lot of.
- [16:11]
B
Yes, there is something called a give get. And when you're interviewing for a nonprofit board, you should ask the nominating committee if there is a give get, what it is, what that expectation is, how, how well enforced it is, because that's a big part of it. They are looking for you to bring people into their community who would want to come to the gala, contribute funds. We're right now at the end of year fundra and campaign time. And so it's important for you to. It is expected that you will bring your community to the table to help fund these institutions, especially as government funding is becoming so much more challenged in this environment.
- [16:58]
A
Wow. Yeah, it's good, good. Very good information to know. And earlier you talked about the audit committee. So a lot of people talk about if you're not coming from a financial background, it's good to sit first in the audit committee and pay your dues and learn all the financials. Do you. Is it your recommendation as well for somebody who's not coming from finance?
- [17:18]
B
Yes. So just to set the set the stage a bit. In a publicly traded company, there are three committees that are typical and there could be others, but one is audit and risk, one is nominating and governance, and the other is compensation. And so when you come onto a board, it is typical that someone goes through the audit committee so that you can understand the financials. The financial statements include a statement of purpose for the business. You are working on the quarterly release of our results. And so you're understanding where the risks are, how we talk about the business. You're spending a lot of time with investor relations, you're spending a lot of time with the CIO and the cto, understanding the technology underlying the business, because that all has an impact on the financials. And of course, you spend time with the cfo. I learned so much about our business model, the uniqueness of it, the levers in our business, our capital structure, because I was on the audit committee. There are two levels of participation in the audit committee. One is a certified financial expert. Those are typically people who've worked at places like pricewaterhouse or Deloitte and who have been actual auditors working for companies. You don't have to be that to be on the committee, but you do have to be familiar. And this is where the MBA comes into play. The P and L, the balance sheet, the cash flow, understanding the differences between them and being able to discern when you're getting good advice or bad advice from your cfo, your cio. All those things require a certain level of business acumen. And I think it's not talked about enough how financial corporate boards actually are. We want to talk about strategy, we want to talk about our customers. But in fact, my experience has been the large part of the conversation is really around the financials and how we are presenting ourselves to the street and managing the risks in the business.
- [19:27]
A
Business, yeah, because the shareholders, that's what they care about, right? This stock is going to end and what's happening and then, you know, when they're not happy. So you have to make decisions and then if you don't manage it accordingly, then years later or even quarters later, you're going to hear from it. And that's the tension between the street and the boardroom and of course the company and the rest of the. I think that's very important.
- [19:55]
B
Now, I will say that I have graduated to the nominating the Nom Gov committee, and that is as of our last meeting. And what's exciting about that committee is understanding board composition. Do we have the right board composition? How is the board performing? Do we have the right culture? Are there things we need to put in place to educate our board members? Two hot buttons for us right now are education on cybersecurity and education on AI. Not only how AI would be used for our grocery business, but even how AI is being used today for board members to help them prepare for meetings. What kind of information is safe to put into a public platform like ChatGPT? What are the rules of engagement? How can you use it? So there are lots of businesses springing up around AI and better use of AI for boardroom participation and preparation.
- [20:52]
A
And also how AI accelerates everything that cyber threats and cyber security hacks. So that's also the scary part of the evolution. People talk about how artificial intelligence also is a challenge now to the security of the Internet. So everything that we've worked so hard to build, now it's easier to hack because a lot of things can be hacked a bit. There's an acceleration of the technology that hackers can use, which is also one of the challenges. So let's talk a little bit more about the long term skill roadmap because a lot of people, and talking about women, we're talking about ambitious professionals are at director or vp. They're interested in figuring out how to get, how do I get to that first leadership role, whether it's getting to the director or VP role. And some of them it's like in 15 years I want to get to that level and, and gain to join a major corporate board. What are the two marketing functions like do you think you should get exposure to before joining a board or being board ready?
- [21:57]
B
So I do think it's important to have a diverse set of skills in order to prepare yourself to be on a board. And then I want to make sure that we talk about the age question. Okay, preparation. So let's say like you and I are working at LinkedIn, but every quarter at LinkedIn there is a release of the Microsoft results. Being curious at whatever company you're working for, but reading the financial statements, understanding what our CFO is saying about the business, looking at the financials from Microsoft in that case because they own LinkedIn, and being attuned to that quarterly rhythm of the business is something that anyone can gain no matter where they work. But just understanding that looking at the analyst reports, watching the stock price, it's something that you can do without even being on that trajectory. The second thing is asking for different kinds of assignments. Way, way back when I was at Levi Strauss, I was able to participate In a project that was commissioned by the CEO, we wanted to understand a different way of forecasting the business. We were thinking about channel shifts, and I was able to work as a. As one of six people. I think it's about six of us on this team. But we had direct exposure to the CEO and to this boardroom conversation. So the kind of thing that you raise your hand for as you're a director, you're seeking this kind of experience later in your career is raising your hand for interesting opportunities. Cross functional. It might feel like it's a little off the career track, but what it's actually doing is allow you to have visibility and be in those rooms where the conversations or where the air is a little more rarefied, the conversations are a little bit different.
- [23:50]
A
I love that.
- [23:51]
B
Let's get back to the question of when this should start. So there has been sort of a tradition that at age 72, people start thinking about rolling off boards. There's a conversation that that number is going to become 75, maybe 78. Certainly on the board that I was on, there were people in their 80s. Actually, there's one person. Person who was 90 who just rolled off the board. But. But generally know that that window means that if you're going to have a significant number of board experiences under your belt, being in your 40s and starting to think about this is not too early. At the event that I attended last week with black women on boards, Roz Brewer was there. She's the interim president of Spelman College, but she's also been on a number of boards. Boards. And she said that she started in her 40s, usually as what we call as a sitting executive, as someone who has a role in a company, a 9 to 5, you're typically allowed to be on one board at a time. And so she said in consecutive sequence, she was on the board of companies like Starbucks and United and other. But she was gaining that experience so that by the time you get to your 50s or early 60s, you have a significant portfolio of companies that you've served. That's actually something that I haven't done. And so now, as I'm trying to expand, the one thing I would tell my younger self is to start sooner. But you know why we don't start sooner?
- [25:27]
A
Why?
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B
Tell me. Because these are not conversations that are held around our dining room tables because we don't have. My parents were professionals, but they certainly didn't know anything about advising me on being on corporate boards. And so there are so many people who have an Advantage who are able to talk to their parents, talk to their dads, talk to their uncles and their aunties about doing this. And we have to learn this on our own. And that's why organizations like Black Women on Boards exist, because we need that, that same kind of dinner table conversation to tell us when to start thinking about this. But. But for me, if I could do it over again, I would start thinking about it in my 40s and build experience. Because the people that we've been interviewing at my current company for our board refreshment, my God, they're in their 50s and they've been on three, four, five, six boards. And so they've been doing this all along. And there are people who are sort of professional journeymen who've been on many boards who are able to become experts in governance, experts in audit. And it starts early, earlier than I ever imagined.
- [26:41]
A
I think we get the message to start early. And fun fact, Gail. When I was in Canada, which was 14 years ago, I was offered a seat on the private board. And at the time, I didn't have the network to tell me, yeah, you're just gonna have to fly back. Back from California to Montreal Quarterly. I said, oh, no. And then I referred it to somebody else. But that's like, what, 15 years of difference, right? Sitting on a board on a pain.
- [27:08]
B
I would have told you to take it. Right.
- [27:10]
A
I didn't know you. And I was already a director at Deloitte in the consulting firm. So it's just things that you don't know, but you don't have access to the right information at the right time. And I think the world has changed. That's why we have podcasts like this one, and that's why we have networks like Black Women on Board. And that's why we're circulating and we're more vocal. Now I want to bring you to my favorite new place, which is called the Hot Seat. It's a seat where we talk about rapid fire career questions. I'm ready to help really ambitious professionals or serious about their career acceleration, gain a really wise perspective about what to prioritize when you think about their career. Okay.
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B
Okay.
- [27:52]
A
Let's go, Gail. Okay. Welcome. What's the biggest lie society tells us about success?
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B
It tells us that there is a corporate ladder. There is not a straight line from entering your career to ending your career. It is a curly cue. It is a, like a roller coaster of many twists and turns. And, you know, like from banking, retail, technology, board work, who knew? But it's not a Straight line and embrace the diversity in your own career.
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A
Awesome. What's your cheat code to success?
- [28:32]
B
Pattern recognition. Having enough experiences across the board, different companies, different sizes, different functions, so that when you're in a new situation, you can say, ah, this looks like something I've seen before. I have an idea. I can apply it to a situation where it turned out well, it turned out badly. But it's that ability to come into a situation and apply some sort of personal framework. So pattern recognition, I love it.
- [29:01]
A
So what's one lesson you wish you knew when you were 20 years old?
- [29:08]
B
Well, you know, I think this, this idea of, of becoming board ready and being cross, functionally capable is something that I wish I knew. I mean, you think in your 20s you have to go narrow and deep and learn one thing, but I think it's that diversity of experiences that really does help. So no matter what you're choosing to do, be curious about all of the functions and don't get too narrow. I think in my career, probably getting very narrow on marketing as opposed to thinking about the entire organization is something that I probably would have told myself in my twenties. One good way to do that is being a consultant. You mentioned being a consultant at Deloitte. I think consulting does tend to give you that C suite perspective. And that's so important.
- [29:58]
A
It's very important. What's one thing the top 5% of achievers do that 95% of people ignore,
- [30:06]
B
Meditate, breathe and live in their bodies? I have a practice of journaling every morning. What do I want to achieve? Sitting here, right here on my desk is what's important today. So it's getting very focused. And one practice for doing that is journaling, meditating and being highly intentional. I think the top 5%, from everything that I've read, they're very intentional. There's a spiritual quality to that that's not religious, but it's that that single minded area of focus and doing it every day, doing it every day is one of my practices and it's been a real differentiator for me.
- [30:47]
A
I love it. So what's your one line lesson every founder should hear?
- [30:53]
B
Make sure there's enough revenue coming in before you get too busy spending. One of the things that I'm recognizing as I am founding my advisory business now is that that lots of money's going out. It's going out to the trademark attorney, it's going out to the llc, it's going to the tax advisor. Get some money coming in, right? So find a way to Balance that so that even in the early years there, you might be operating in the red or you might be investing more than you are producing. Make sure that you have a clear line of sight to generating revenue and generating revenue early, even if it's many, many small pieces. But I think that's one of the things I've hear people talk about is becoming a problem early on is too many outflows. You don't need a perfect logo. You don't, you don't need all of the bells and whistles. You just need a strong foundation, a value proposition, a few clients and just
- [31:56]
A
get going, get the revenue in. She said it was the most powerful habit that made you rich.
- [32:07]
B
Determination. If there is one thing that my father told me, it's that I am a survivor. And so it is that mentality of take no for an answer, continue to push that rock up a hill, be determined, and that it's, it's finally paying off. It's paying off. But never take your eye off that prize, as they say.
- [32:33]
A
I love it. And lastly, what's one rule that's common in all the CEOs and founders that you've seen?
- [32:41]
B
Curiosity. The endearing thing about the new CEO for the company on which I'm the board, on the board of Grocery Outlet, he's extremely curious, asking questions. Actually, I have an even better example. We have a new CEO at the nonprofit that I am on the board of and she attended yesterday's board meeting and she is a very loquacious person, very opinionated. She sat through all of the board meeting. She made a brief introduction and then for the rest of the meeting, she listened. She wanted to learn. So listen. Learn listening tours, being curious not only with your customers, but your internal listening with your employees. It's so, so important to be a good listener.
- [33:31]
A
That's amazing. Thank you so much for coming to the driving impact the top 5% method. I feel like our audience is richer than when is leaving Reacher richer than when they came in. So many wise advice and I think it's so much wise advice and I think it's very helpful to hear your own story, but also your own path to your, your biggest, the biggest board, that publicly traded board. But also how you've been able to successfully have these nonprofit seats and made them very work very well for you.
- [34:06]
B
Yes, yes. It is information that I'm happy to share. It's our obligation to share it with people coming behind us. So thank you so much for giving me this opportunity.