Women in Wealth: Why It's Their Moment

We spoke with the two wealth management and fintech experts about the past, present and future of women in the business. In addition to highlighting the twists and turns of their own careers, Nash and Rudin explain why digital innovation matters to everyone in the industry.

Investment Advisor: How did you two meet?

Cheryl Nash: April and I met in 2012 at the Tiburon CEO Summit in San Francisco. That was the first time I went to this conference.

We were two of the very few females in the room, and we saw each other and later met in the ladies' room. From then on, we became fast friends. When I learned that April had her own firm, we started working together.

April was influential in helping me and my career. Actually I'd say she's probably been along for the ride with me. Since 2012, April's been very instrumental in helping our business think about what marketing looks like and think about how you put sales and marketing together to really put out a story that encourages clients to buy from a fintech/wealthtech perspective.

And now, growing a business via sales and marketing is one of the areas that I focus on, along with getting involved with LinkedIn and social media. She's really helped us understand the importance of [LinkedIn/social media], how you use it to your benefit and how you use it as a sales tool.

When it comes to where women in the industry are going, it's really about where we come together in today's world to support each other. For instance, April is a phenomenal marketer, and she will always retweet, like, share and support many people's information on social media. This makes a really big difference, because obviously the readership then is that much larger.

Many people appreciate what she does and who she is. And outside of that, we've also become friends. When her son was looking for an internship, she called me and asked if we had anything going on at Fiserv. We brought him in, … and he got to learn the industry. I did the same thing with my son. He became an intern and is now working in this industry.

This is where women excel — you build a relationship and then you make sure it's not just a relationship in which you say "hi" and have a cup of coffee. But instead, you actually help each other and work together. It's been apparent in our industry that there's a need for this, as there aren't many of us who can work together. All of this goes hand in hand with growing together. We both grew from our relationship.

April Rudin: I felt like a fish out of water at that Tiburon conference. That's what I remember. This was the first time I went to it, and it was a bit intimidating for me, because it was a CEO summit with a lot of very senior people.

I didn't really have expectations, other than being happy to be included, and I was taking everything in. At a break, I went to the ladies' room, and there was Cheryl with that beautiful, friendly smile and her willingness to always say "hello."

I said to her, "Look, there's no line in the ladies' room. And I put that hashtag on Twitter, and we tweeted #NoLineInThe LadiesRoom. Then I wrote a Huffington Post blog in which I quoted Cheryl. The whole idea of that blog, interestingly enough, was about how the future develops.

Men almost have to be forced to be together with others in some ways. It's lonely at the top for men and rare to find peer-to-peer relationships, whereas women seek each other out, and that's what we do naturally, right?

Cheryl and I became fast friends right there in the ladies' room without any introduction; we introduced ourselves. We didn't have any pomp and circumstance going on. I've known a lot of people and worked in many organizations, and then have run my own firm since 2008.

Out of the people I know in wealth management, something like 75% of people have either worked for or with Cheryl. She has touched their careers. So, whether she's supervised or directly worked alongside them or they've been a client, she's had so many different types of relationships with people. And on top of that, you won't find anyone more universally loved and respected than Cheryl.

With her organization and its structure, it's been really easy to raise Cheryl's brand as a personal brand and work side by side with her. There's not another person like her who's so universally respected, admired and checks all the boxes, and … she's not even old enough to have won a lifetime achievement award — she's a mid-career professional.

Also, other things that I so respect about Cheryl are that she's a great listener, a great learner and is so eager to help everyone. At the same time, she's a mother, a president, a CEO and a fintech expert. She fulfills so many different roles. … That really makes her unique in the industry.

As for her most recent job change, she went from being an employee of a global multinational organization to a leadership role as an entrepreneur. She did it with zero fanfare and is super successful, though she's now in a very different arena. And she did it with … her friendly smile and didn't miss a beat.

What was your career path in financial services and technology? And what advice would you give to others based on your experience?

Nash: When I was in school, I did not think I was going to ever lead a technology organization, let alone even be in a financial services organization. I actually wanted to be a weather [reporter] on TV. So, this was not really my career choice, but I fell into it as so many people do. I got an internship opportunity, and I took it.

My dad knew a guy who ran a brokerage firm in Chicago, which [later] … got bought by Stifel Nicolaus back in the 1980s. The family who owned the brokerage firm decided to start their own technology company and help [other] brokerage firms become more automated. Back then everything was still manual. They offered me a role in whatever I wanted to do. There were four people involved.

I grew up in this industry, literally, at the same company. But it's been bought three times, so I've had very different roles all three times. Plus, I've probably played every role, besides development or quality assurance. I was in and led client services. I was in and led product management.

My advice to others is to take every opportunity given to you. Even if you don't think you're ready for a role, take that role because it does lead to bigger things. I had no idea, years ago when I was a client service rep, that I would become CEO of the company that I was in. I took on a lot of things that I wasn't comfortable with, but I also had good sponsors and mentors along the way. That's so important.

I would tell women, especially in technology today and in financial services, to give it your all. Learn as much as you can. Find a network that can help, with people … who can help you. But don't say "no" to opportunities.

There are so many times when I was given an opportunity that I didn't think I could do or didn't think that was what I wanted at that point in my career. I just did it, and it's helped me … to be well rounded.

Like April said, it's been about knowing a lot of people. I did sit next to clients and then also helped lead clients through strategic initiatives at their firms. It's been an amazing career, but it's not something I set out to do.

I talk to college students all the time. I tell them that if you want a career that's enriching and that you can be successful in, look at financial services and look at technology. There's an urgency right now to get more women and people of color into this industry. What a great opportunity for us to lift others up, get them in [the door] and help them grow. Nobody can really do it alone.

Rudin: Sometimes I call myself the original millennial girl, because I was hired by the president of Kelly Services, a [staffing] services company. He asked me one question. "Do you know about the Wang Word Processor and the IBM PC?"

I said, "Yes." And he said, "You're hired, because we don't. We have typewriters in our offices, and there's also dictation. All of this is changing in front of our very eyes."

Who did they hire back then? The one who was young. It was my job to go out and find the technology they used to automate their offices. And it [involved] training, testing and standards in an area that no one knew very much about at the time.

Kelly ended up buying a company that was started by Eric Becker's brother Doug Becker. Eric is a founder of [RIA] Cresset. [The brothers also funded the private equity firm Sterling Partners.] I've known them for more than 30 years.

Also, I met Bill Gates like 10 or 15 times in the 1980s. We were getting all this media [coverage] from publications like "InformationWeek," and I was the immediate spokesperson. It was the first time I saw a staffing company become a technology company.

If you fast forward, I relocated to New York, had some different jobs, took some time off and had my kids. When I was going back to work, New York had the garment center and financial services. I like to buy garments, but I didn't think I wanted to work in the garment industry.

I started working for a friend whose family was credited with inventing the multi-family office. I started looking around and saw that this wealth transfer was happening. But the brands in wealth management looked old, stale and tired. They had a lighthouse, a yacht and accessories, or a picture of a couple on a beach — like that's really retirement. I thought to myself, "I can do better. Someone can do better."

I went to a friend of mine who was running a large bank and trust. He said to me at the time, 12 years ago, that I "was too old to be an entrepreneur; banks would never hire outside firms; high-net-worth individuals would never be on the internet; and social media is a fad."

Instead of being discouraged by all this, I was encouraged. I thought, if this guy thinks that everybody would say those things, then that to me looks like an opportunity.

So, I went from one industry working at Kelly Services, where I had great mentors and sponsors and worked for some great women, largely women, and made the switch to financial services, which is largely male. That was really different for me.

What's your overall view of the presence and status of women in financial services, including technology?

Rudin: Some large firms have numbers that don't look so out of whack with the overall diversity and inclusion [goals and the general population]. That's because marketing is filled with women, human resources is filled with women, etc.

There could be a large number of women at a firm, but what areas of the business are they involved in? Generally speaking, it's not operations, product [development] or this type of focus, and they tend to be more concentrated in supporting roles.

That's made Cheryl, for example, a really great role model. She's been hiring women across her organization rather than just deep in parts of her organization — in product and operations, not just human resources and marketing.

Nash: Another issue I've focused on is women in our industry from one to five years after they've joined it. After five years, in terms of their career path, they're either stuck — and likely will stay where they are and they'll be happy with that — or they're going to get out of our industry.

We're trying to keep women in our industry. There's a bigger sense of urgency right now — with the push for diversity and inclusion — in helping women rise.

It's about who you know in your industry or your business and finding the right sponsor. Or the sponsor is going to find you, as they look for people who are hardworking and who they believe should take on a stretch role, right?

This means finding someone who's going to look out for you and who'll speak about you in the room when you're not there. If you look around, it's disappointing when women leave our industry.

With the pandemic, there's so much that women have to do — with remote schooling for children, taking care of parents and all the things generally put on women.

Within our business, we've made sure that we're very flexible right now. If you have young kids at home, take care of those kids when you have to and be flexible in your [work] hours, if you're in a role in which you can.

We say this all the time. It's one of the biggest things to do today. If you want women in your organization, and even men today, you need to be flexible. There's a big emphasis right now on keeping women in the industry, keeping women in your firm and helping them find a path so they don't leave. After the five-year mark, what a knowledge base walks out the door when that happens. It's really hard to bring that back in.

How do you see this industry encouraging women and men to become as tech savvy as possible, so their careers can grow?

Rudin: Cheryl and I don't look like the tech "geeks" or something like that [stereotype]. We don't look like what you might think of [related to] technology so many years ago. You know, there's the management information systems or information technology department, and that's for the guys with the pocket protectors. I'm too cool. That's not where I belong. I belong in the front office, with the clients.

But what we've seen over the past years has been that technology's become pervasive. You can't not be in technology. I don't know why people are sometimes surprised about fintech. That [term or concept] is a passing fancy — because what isn't are today's technology companies. I operate a small firm; we're a technology company.

You can't not operate without technology today. There's the notion that we have the "digital natives," brought up with lots of technology, and the "digital immigrants," who grew up before the widespread use of technology. Our children, mine and Cheryl's, are roughly the same ages and have grown up with technology.

The next generation knows that technology is part of the way things work and that it's embedded in work. It's not separate. We don't have a separate technology department at my firm, for instance. If you look down the road and ask who's head of digital, is there really one head of digital? Can there be a head of digital? Isn't that everyone's job?

Those in the next generation are learning about technology at such a rapid rate by using it and gobbling it up. When you contrast those individuals and their ages with the average age of a financial advisor, being over age 60, you start to see the problem.

Generally speaking, women sometimes may not want to think of themselves as sort of geeks or numbers people. That's another misconception about being a financial advisor — that you must be a numbers person, when really it's addition and subtraction.

There are tons of technology products that can help with planning, and women are natural planners — if you look at any type of statistics. Women are natural savers. They like to help people. They're very well suited for the career of a financial advisor.