SALLIE KRAWCHECK: If I wanted to become senior in the industry, the odds were stacked against me. No other woman had made it to the top.

SHELLYE ARCHAMBEAU: I’ve been an outsider my entire life. I was not only the only Black girl in my class, but I grew up being, frankly, bullied — verbal abuse, physical abuse, got pushed down, knocked down, beat up. I mean, it was not good. So, it was very clear to me that the odds weren’t in my favor.

TOPE AWOTONA: I grew up in Nigeria and I just knew that traditional growth playbooks wouldn’t work for me. Disadvantages can actually be advantages. But I just had to do something different.

BOB SAFIAN: That’s Tope Awotona, founder of Calendly, and before that Shellye Archambeau, former CEO of MetricStream, and Sallie Krawcheck, founder of Ellevest,

speaking live at the Masters of Scale Summit in a session called “Think Like An Outsider.”

I’m Bob Safian, former editor of Fast Company, founder of The Flux Group and host of Masters of Scale: Rapid Response. 

I wanted to share my discussion with Sallie, Shellye and Tope because succeeding in today’s chaotic economy requires doing things differently.

These three leaders learned that the hard way, by overcoming obstacles that might have derailed others. 

Sallie was a pioneer on Wall Street, breaking the glass ceiling at institutions like Citigroup and Merrill Lynch. Shellye fought her way into the CEO’s seat in the tech world, a rare black woman at the helm. Tope, who developed his entrepreneurial spirit in Nigeria, chose to build scheduling app Calendly in Atlanta, rather than defaulting to Silicon Valley.

They were each outsiders, and they continue to think like outsiders.

Their stories aren’t just inspirational. They are packed with lessons about how each organization, and each of us personally, can benefit from an outsider mindset.  

Let’s get to it.

[AD BREAK]

SAFIAN: Sallie Krawcheck, here directly next to me, founder and CEO of Ellevest. Tagline, a financial company for women by women.

KRAWCHECK: Yes.

SAFIAN: Right? Also, former CEO of Sanford Bernstein, Smith Barney, Merrill Lynch, CFO of Citi. I don’t know, who am I missing? Some of the ultimate insider enclaves.

Tope Awotona is the founder and CEO of Calendly — grew up in Nigeria, now on Forbes’ billionaire list, not via Silicon Valley. And then Shellye Archambeau, who grew up wanting to be a CEO, and then grinding her way up the ladder at IBM, realized this is not going to happen here if I do this this way. And she took a different tack to break into the corner office, which she did at MetricStream. She’s now on the board at Verizon and Nordstrom and elsewhere. 

You’re all terrifically successful and also decidedly not traditional. And I think those two things are related to each other. 

Sallie Krawcheck on the gender investing gap

SAFIAN: Sallie, you have a story you want to start us off with?

KRAWCHECK: My story starts when I was a 26 year old young woman in investment banking at Solomon Brothers, so on Wall Street. And one day, I looked up from the spreadsheet I was working on and realized I was the senior woman in my department, at the age of 26. And had a further realization at the time that if I wanted to become senior in the industry, the odds were stacked against me. If I did it the way everyone else had done it, no other woman had made it to the top. I was fortunate that my next job was as a research analyst. Because I also came to the conclusion as a research analyst, that in order to be successful there, I had to really have something to add.

My first research report was on a life insurance company, which was growing in the lending business. And all the analysts saw, there’s growth there. I said, let me dig deeper. And what I saw was a picture of deteriorating credit quality.

So I wrote my first research report called, Whoa, Nelly, American General. And I was right. We today call these loans, subprime loans. And so I’ve approached every job I’ve had with… is there a different story? And most recently, in founding Ellevest, I started to really think through the problem that women have 30 cents of wealth to every dollar a white man has. Black women have a penny.

When you look at the drivers of this, it’s the gender pay gap for sure. But there’s also a gender investing gap. My industry knows this. Men and their financial advisors, there’s perfect product market fit between a middle aged white guy and his financial advisor. I love men, I’ve been married to a couple of them. There’s nothing against… But white men trust their financial advisor more than their doctor. The narrative is, women are risk averse. The narrative is, women aren’t as good at math or don’t like math. The narrative is, women need more financial education. Maybe, what the industry is putting out is perfect and women are the problem. Or maybe, in an industry where 99% of mutual fund dollars are managed by men, mostly white, 98% of investment dollars are managed at companies run by men. 86% of financial advisors are men — average age, low 60s. Maybe they built the business for themself.

Maybe, women… Maybe women just aren’t buying what they’re selling. And what if we build the first wealth tech company centered on what women are looking for? There’s still much to be discovered if you step away from the conventional thinking.

SAFIAN: Shellye, you look like you have a question for Sallie? 

ARCHAMBEAU: Sallie, typically when you start something new and you’re the first one to do it, which you did obviously with Ellevest, there’s some unexpected things that happen in that process. So what was most unexpected when you actually started this new model of trying to actually cater to the women who didn’t have a model for financial advisors?

KRAWCHECK: Everything about a start-up is hard. There’s nothing that isn’t difficult, and you’re always a step away from, for those first months or years, from failure. I’d say one of the biggest surprises, interestingly, is when we launched and put out those first ads, that we are unapologetically for women, by women.

There was a good double digit percent of women who said, “How dare you? We don’t need something for women. We don’t need your dumbed-down version. We don’t need your have a chardonnay and let’s talk about stocks together approach.” Eventually they would go into the product and look at it and come out and say, “Actually, these are highly personalized portfolios.” Actually, they take into account that women live longer, earn less, salaries peak sooner, take more career breaks.

So, hey! This is more sophisticated. But what was really interesting is the messages we get from the patriarchy as women, that not one single solitary woman said, “It’s for women. It must be better.” Not one. And so, the surprise was we not only had to overcome, we got to have a product that works and we got to have a team that’s great, that we actually are part of a cultural conversation in which we’re trying to reverse the point of view of, “Oh, I’m risk averse,” when these things really aren’t true.

Tope Awotona on how his mindset as an outsider fueled him

SAFIAN: So, Tope, do you have an outsider story for us?

AWOTONA: Oh, man! Do I. I think all my life I’ve sort of been, I know, the odd man out from … You know, I grew up in Nigeria and I was you know …

I love you guys too…

Yeah, I grew up in Nigeria and, in middle school, I ended up skipping a few grades, which meant that, in high school, I was two years younger than my classmates, which is at that age, that’s a big age difference. So, just always sort of stood out in one way or the other.

But when I started Calendly, in Atlanta in 2013, nine years ago, I was an outsider for many, many different reasons. One, I didn’t have a successful track record as an entrepreneur. As a matter of fact, I started and shut down four different businesses. In addition to that, I was based in Atlanta, not in the traditional tech hubs of San Francisco, Seattle, Boston, et cetera. And my background before that, I was in enterprise software sales, which is not really the background most people think of when you think of tech CEOs and tech founders.

So, for all these different reasons, I was an outsider. And so, recognizing that I was an outsider, I just knew that traditional growth playbooks wouldn’t work for me. I could probably not count on raising larger amounts of institutional capital. That’s probably not going to be a viable option for me. And so, I knew that I just had to do something different.

One, I knew that I had to be the first check-in. There was no rich grandparent or rich parent that was going to fund this business. And so, I raided my 401(k), emptied it, even took out some loans to start the business. In addition to that, I knew that I needed a business model and a growth strategy that wouldn’t be incredibly capital intensive. And so, ended up doing things like, built a freemium business model, so allowed a lot of people to use the product for free. That ended up driving virality and word of mouth.

And till today, still the biggest growth engine for the business, but at a very, very low cost. Because I wasn’t spending a lot of time raising money, it also meant that I had more time to spend with customers and I knew their problems better than anybody else did, which allowed us to build a great product. And also when you don’t have all the capital, forces you to maniacally prioritize. So, through a combination of all those different things, and I did raise a small seed round in the early days of the business, we were able to grow the business to almost a hundred million dollars in revenue without any outside capital.

Thank you. Until today, the company continues to be profitable, which is a rarity for companies of our size and scale and our growth rate. And so, the moral of the story is, there are many, many different ways to approach being an outsider. You can assess all your advantages and all your disadvantages, and you can get hung up on all those disadvantages. But I actually think if you look very closely, those disadvantages can actually be advantages, as happened in the case of Calendly. So I think that’s the thing I would encourage people to think about.

SAFIAN: Turn those limitations into opportunities when you can. When you can. Do either of you have a question or a reaction to Tope?

ARCHAMBEAU: Tope. When you were building and scaling and you actually didn’t have the dollars, now as you’re getting bigger, everybody wants to put money in. So, what did you use as your framework? A lot of the people here, over time, will raise money and all money is not the same. Any perspectives you might share about that part of it?

AWOTONA: We have very, very ambitious goals. It turns out that even in spite of the growth that we had and success that we had, there’s still this validation that sort of comes with institutional capital. There are still a lot of very smart people, which the primary way in which they judge the quality of the business or the prospect of the business is whether it’s been validated by an institutional capital.

And oh, by the way, your customers, too, especially for us, we were looking to move upmarket and acquire more enterprise customers, there’s this validation that comes with institutional capital. So, what guided us in picking investors we wanted to partner with is, do they have a track record of taking or working with businesses like ours to accelerate their growth and achieve better outcomes? Do they have a network? If you want to build a great business, it takes a village. You need all the allies you can in this very tough journey.

SAFIAN: Hmm. I love that. So, even as an outsider, sometimes you have to be looking for things that can be your conduits to that insider community when you need it.

AWOTONA: Yes. 

SAFIAN: What Sallie, Tope and Shellye are discussing here is how taking an unexpected approach can unlock opportunity. The status quo is always difficult to break down, but if you see others accepting things unthinkingly, that often means there’s a better way.

After a short break, we’ll hear Shellye explain how she took an unconventional route to the CEO suite, and then operated in an unconventional way.  

[AD BREAK]

SAFIAN: Before the break, we heard Ellevest’s Sallie Krawcheck and Calendly’s Tope Awotona explain how thinking like an outsider propelled their success. Now, Shellye Archambeau explains how she orchestrated a dynamic turnaround as CEO of a struggling tech firm, by embracing her outsider roots. 

Then, we’ll hear lessons about instilling outsider thinking in an organization, reinforcing the right values and behaviors, and staying confident in the face of criticism. 

Let’s join back in. 

Shellye Archambeau on orchestrating a turnaround

SAFIAN: Shellye, you have a story for us?

ARCHAMBEAU: I’ve been an outsider my entire life. Growing up, we lived in neighborhoods, where I was not only the only Black girl in my class, but many times in the school, other than my family members. And this was the ’60s and ’70s, a time when for as many people who felt there should be civil rights, you had just as many that didn’t. And they let this little Black girl know that.

So, I grew up being, frankly, bullied — verbal abuse, physical abuse, got pushed down, knocked down, beat up. I mean, it was not good. So, it was very clear to me that the odds weren’t in my favor. And what I learned was, one, I had to pay really close attention to what was happening around me. And that was for self-preservation. And number two, I learned it’s important to do my own research, because what people tell me, isn’t necessarily in my best interest.

So, fast-forward on those two things. I get my opportunity to be CEO, which as Bob said, was something I was absolutely striving for. Vinod Khosla hires me to be CEO of a company called Zaplet. Zaplet, at the time, was, frankly, failing. It was failing. We were burning a couple million dollars a quarter. This is 2003. The dot-com bubble had burst and Zaplet was selling a product, and nobody’s interested in this product. So, it was clear that we needed to pivot. But the company hadn’t realized it yet. It wasn’t that we had a broken value proposition. We had no value proposition.

So I dusted off what I’ve learned early on. Number one, you look outside. I went and spoke to the smartest people I could find. The question I was asking is, “what is a problem you’re seeing in corporate America that’s really hard?”

Roger McNamee. Some may know that name. Roger said to me, “You know, Shellye, this compliance stuff is just killing companies.” He goes, “I don’t know what you do about it, but compliance is a real hard problem.” Well, I dusted off skill number two, which is you always go do your own research.

So, I did research around compliance with the team, and you know what? It was a big problem and there’s huge fines that companies pay. I’m like, “All right. Now, I have a platform,” because Zaplet had built a platform. I was just trying to find a problem to solve.

So, we decided to take that platform and build the apps ourselves. That would solve compliance. We called it comprehensive compliance and risk. And that’s what we were going to take to market. The only problem is, I still had no money.

So, Vinod Khosla introduced me to a company called MetricStream. They were a small startup doing, really, quality compliance. We put the two together, took the MetricStream name, much better than Zaplet when you’re trying to sell to CIOs. And that’s what we did.

And the good news is, over the course of several years, we built MetricStream into a global market leader.

So, listening to the outside… Thank you. But paying attention, real attention. I tell people, good advice, good ideas fall from the sky. We just have to be listening for it. Just listening for it.

Shellye Archambeau: “Don’t fall in love with your product.”

KRAWCHECK: I would love to hear about, you were on a glass cliff. You were leading a business. Probably those who look like the norm of a CEO maybe weren’t interested in leading. You just said, “People didn’t know there was a problem.” How do you lead as such a visible outsider and outside leader? How do you lead the organization through that and the people through that pivot?

ARCHAMBEAU: Sure. Pivoting is not easy. I mean, they’d spent years, a few years building this product. They loved this product. And I’m going to come in and say, “Hey, everything you’ve done is kind of worthless.” No, that doesn’t work.

So, what I did was I told them a story, which I’ll share with you, because this is a problem that many start-ups fall into. You put all your time and effort into this product. You give the product everything it needs, all the time to focus, the whole bit. You treat this product kind of like your baby. This is your baby. Well, for those of you who’ve had a baby or been around babies, no one can tell a new parent that their baby is ugly. Nobody. Right? Oh, no, no. You just haven’t looked at her in the right light. Wait till you see the face she makes when she burps. No. Be a beautiful baby.”

Well, the key is, don’t fall in love with your product. What you want to do is fall in love with the market that you’re targeting. That’s where you want to put all your love, caring, and feeding. You want to meet all their needs, all their requirements.

And so, coming into Zaplet, it was basically sharing the story of: listen, yes, you’ve birthed the baby and that’s wonderful, but that’s not the actual baby you were trying to birth. The baby you’re trying to birth, this the problem that you’re trying to solve for all these people. So let’s understand them, what they need, and what they require, and take everything we’ve done and just morph it to meet their needs. So, helping them, you have to give the inspiration the picture, so that they feel good about what they’ve done, but want to work towards where they need to go.

How to instill an outsider mindset amongst your team

SAFIAN: I’m curious. All three of you have backgrounds and legacies as outsiders. When you’re running a team, not everyone on your team has that history, but you want to instill that kind of outsider thinking into the way they operate. Are there tips or suggestions or experience that you could share with this group, share with each other, about how you get a team to have outsider thinking, when maybe that’s not the place that they start from?

ARCHAMBEAU: To me, it’s how you ask the questions. So, in leadership meetings, when you’re pulling people together, you ask the questions. So, somebody share… what’s the newest thing you’ve learned in the field right now? You just start asking questions that are actually outside in. Once you do that and people realize you’re going to continue to do it, guess what? They’re going to go find those answers so they have something to say during that conversation. But I find if you ask the right questions and just make it consistent, people realize that’s part of what they’re supposed to do.

AWOTONA: One of the things we do is we have core values that really reflect that outsider thinking. And a lot of companies have core values. We’re not unique in that. I think what we try to do differently is really live by those core values.

So, two core values that came up from our origin story are one, find a way, which is really about being resourceful and being scrappy. And we reward that, so it’s not just a value that we have on our website. We have awards for that. We recognize that and the work that people do to reinforce that behavior.

And then the other one we have is: start with human, which is really about human centricity in the decisions that we make. And I, as a CEO, can’t single-handedly just write these values on a tablet and just post them out on a wall. There’s actually a process in which we said, “Hey, let’s take a look at why we’ve gotten here. What are the things we like about the way we’ve gotten here? What are the things we don’t like and what is the way we aspire to be?”

It’s a combination of really making sure that you’re intentional and deliberate in the creation of those values. And then beginning to assess people against that and allowing people to self-select into that system.

KRAWCHECK: One of the really great things about startups is, you get to decide who works there. Whereas our industry is 80% men, at Ellevest, we’re 80% women, we’re 50% people of color. And so, what we did is we brought the outsiders in. We brought in, certainly, people who have FinTech and financial services experience, but our first head of product came to us from Weight Watchers, who was an expert in behavior change in women. And so, we said, “Let’s bring these folks in, reflect the client, the customer back to her.” And so, we’re several steps ahead as we’re building the product, understanding what her needs are because we are her.

SAFIAN: But it’s interesting, because for some of you, it’s about the people. And to some extent, as you’re talking about, Shellye, it’s a little bit about the process, about how you get those people to think a little differently. It’s that interplay… 

ARCHAMBEAU: No, it’s absolutely both. It’s absolutely both, because behavior you want, you won’t consistently get as a leader, unless you are, to Tope’s point, reinforcing it every day with other things that you do. But then you have to build it into just process and help people do their jobs so it just becomes second nature and not an exercise. Exercises don’t last. They don’t scale, they don’t last. You have to figure out how to build it in to how the company actually operates.

SAFIAN: I just want to acknowledge that sometimes being the outsider… I mean in settings like this, it’s like everyone’s cheering, but it’s also hard when you are the one that is the renegade. Whether you’re that within your industry, whether you’re that within your team, as managers, we always, “Oh, we love having that renegade there,” but that renegade isn’t always the one who moves up.

KRAWCHECK: Look, sometimes it’s sort of tough to stick out and people have points of view on you that are based on what’s going on with them, not with you. So, when I did my last raise, someone… “Well, we’re not going to invest in her because we heard she was a bitch.” And I’m like, “And?” But there end up being stereotypes about you when you are one of the few.

AWOTONA: I think you just have to embrace that outsider status. I think it is indeed harder, but I think all great things are, by definition, difficult. But I absolutely enjoy being a contrarian. I get a lot of pleasure in it and yeah, just embrace it.

SAFIAN: Shellye, a final thought?

ARCHAMBEAU: A final thought here is, it can be hard at times, absolutely. Especially when people are telling you, “You should be doing A,” and you know you should be doing B. But just remember, nobody knows you or the company better than you do as the leader…nobody. So, all the rest of this are just thoughts and ideas. Think about them, but be confident in yourself and what you believe, because you’ve got the depth. You’ve got the depth. So just move forward.

SAFIAN: Well, terrific. Thank you, Shellye and Tope and Sallie. Thanks so much.

Listening to Tope, Shellye and Sallie, I’m struck by their confidence. Thinking like an outsider may sound romantic, but it takes courage and conviction. The models of success that are around us can be restricting. To find a new, better way, we have to think in a different way, and do so consistently and intentionally. And when we do, anything is possible. I’m Bob Safian, thanks for listening.