Ainslie, welcome back to the Brand Lab Series. You were on way back in 2016 in our first season, when we started, wearing a different hat and I’m so, so thrilled and thankful that you can come back on, talk a little bit about your evolution since those days, and share a lot of your wit and wisdom around digital. So welcome back.

AINSLIE

Thanks, thanks for having me.

BRIAN

For years, you’ve been at the intersection of technology, personal finance, wealth management, asset management. When we chatted in 2016, you were at LearnVest, that was obviously sold to Northwestern Mutual. Now, you’re at PIMCO. Talk a little bit about why this is important to you, this intersection of technology and finance.

AINSLIE

Yeah, finance is a space where people are endlessly intimidated. Everyone works so hard for their money, but they get really intimidated around what they should do with their money and I just think there’s so much opportunity across the entire industry to make finance easier to understand. And technology and user-centered design is really leading the way in doing that. People are able to see their money, visualize it, and make higher quality decisions, and I just really wanna help people do a better job taking care of their money.

BRIAN

I thank you for that because as someone who uses a number of technology tools for personal finance, for business finance, for wealth management, retirement planning, it’s pretty crazy and can be a little intimidating. And I think what’s interesting is that the bar has been raised a little bit, just overall, consumer expectations. I know shockingly, we’ve known each other now for what, eight plus years, and I think about how much digital has changed just in that time period. But one thing that hasn’t changed, which you’ve talked about for just a second, is that, finance is an intimidating thing for people, and I wonder how much of the problem around personal finance and savings is education, and what can brands do a better job of to help with that education.

AINSLIE

I think there’s a ton that brands can do. And one of the reasons I think PIMCO is such an interesting, fascinating opportunity is, it’s really committed to making sure people understand a part of the market that they don’t understand, which is bonds and fixed income and safe investments. And so, I think that brands need to make sure that they’re speaking in plain terms, they need to make sure that their digital experiences are consumer-grade and really well-designed and really easy to understand and they need to be on the consumer side and make sure that the job is not done until everyone understands the decisions in front of them. And there’s just a lot of really great things that are happening and the industry is being led by other sectors, for sure. Finance is not out in front, but what’s exciting about finance, is that there’s a lot of resources and a lot of really intelligent people that can help shape this new world and it’s a commitment to doing it and then it’s following through until every last consumer understands what to do with their money.

BRIAN

Kind of building on that a little bit, in addition to being a technologist, you have a really interesting background, obviously, in marketing and specifically, in some consumer marketing roles. I know you’ve worked with a number of very well-known consumer-facing brands, including in the CPG space. One of the things I really liked in doing a little background for the audience on PIMCO is, I love this simple brand purpose you have, which is creating opportunities for investors in every environment. Talk about how you guys bring that brand purpose to life.

AINSLIE

Yeah, it’s really interesting. It’s hard to even imagine, but we’ve been in an almost 10 year incredible bull run market, where it feels like there’s nothing that can ever happen than the market going up, and PIMCO as a firm, is really here for all market conditions. We definitely have lots of things that work in markets like this, but then we’re also very conscious and diligent about protecting folks in down markets and making sure that they have a safe place to put their money that can still work for them. I don’t wish a market downturn on anyone, but they happen. And I think it’s going to be wonderful to be working with companies that think about both phases of the market and are really on the consumer and investor’s side in making sure that they preserve their capital, that they have a safe place to put their money, that they don’t have to worry and they can sleep at night, that they’re not going to see their retirement accounts decimated or their hard earned savings decimated.

And so, PIMCO thinks very hard about long-term trends and has lots of solutions for both market types. And I respect that philosophy, because it is bound to happen and I think it’s really great to know that there are really quality companies thinking about both sides of the experience.

BRIAN

I can definitely appreciate that. And I know we talked for a minute about some of the education and the intimidation of the industry. I think the other thing, which again, I’m sure you’ve seen first hand, too, is, it can get so emotional. You’re absolutely right, in all the times that we’ve known each other, the market’s been usually going in a really good direction, but you have some volatility day-to-day, and I think people get so attached to tariffs and the DOW going down a couple of hundred points and then it goes back up. And I think the hard part about that education is that it is a long game, and that you do have to balance, and you do have to understand that you could have a bear market and you can still actually do somewhat well. That’s where really understanding and looking to people with the expertise to guide you through those market corrections and market flows is really important. That’s why I was excited that you’re now heading up digital at PIMCO. It’s gotta be a big job. Describe what a day-to-day role is like for you.

AINSLIE

PIMCO is amazing at many, many, many things: Our portfolio managers, our client service teams. Just an amazing place, but one place it hadn’t traditionally made an investment is in client-facing technology. The founder of the firm prioritized portfolio manager technology. And so, when he left and we have a new CEO, Manny Roman. He is now prioritizing client-facing technology, so our team is here to really now start building out incredible experiences for our institutional and wealth management clients. And what that means is we’re a start-up in this giant company. And so, what’s really interesting is we’re able to bring modern technology, software practices, design practices, product management practices, into this place and people are cheering us on, and fascinated about how things work differently, how user centricity is really the North Star. And I find the folks in this organization so, so, so supportive because they want us to win. We all wanna do the right thing for our clients. Sure, it’s a big job, but I’ve never felt so supported and so cheered on by folks that admittedly don’t understand technology, but they’re like, “Gosh, we want it and we want you to win,” and it’s just a wonderful place to come and work every day.

BRIAN

It doesn’t surprise me that you’re finding yourself in yet another startup-esque role, building something unique inside of a larger organization that has a great and rich history. And as you said earlier, I find it interesting that financial service is… Even on the personal finance side, as well, they’ve been slow to adapt to the technology curve. Some do it, certainly, better than others, but as an industry on the whole, it’s still bringing up the rear a little bit. Digital transformation, like innovation, is such a buzzword and it’s sometimes often overused, but as someone who’s leading digital and has had great success in leading digital at other brands, too, talk about how you see digital transformation and what excites you about what could be ahead.

AINSLIE

Yeah, you can really break digital transformation down into the work itself, creating really world class websites, mobile apps, applying AI, switching legacy systems into cloud-based systems. There’s definitely the work itself, and then there is the way that the work gets done. And what companies are trying to chew through is how much of the work itself do they need to do. Do they have to swap out all their legacy systems? Is it something they migrate over time? How many client products do we need? What are the most impactful for the business? But then there’s also this really interesting question about how much of the new way of working, that agile culture, the Silicon Valley break fast and fix kind of thing, do they wanna bring in to the business? And in financial services, that’s a complex question because we’re very heavily regulated and we’re dealing with people’s money. It’s a really careful balance that you have to walk in, what is the actual work and what is the most impactful work and then how much of that culture, the culture of innovation, culture of agility, whatever you wanna call it, do you wanna bring in as well?

And every place is finding their own way on those topics and for most places, there’ll be things that make sense and things that don’t make sense. And so, what digital transformation leaders really need to do is think about, what is the full set of things that might be applicable, but not try and force a roster of things on a firm if it doesn’t make sense for them. I was in a start-up when there was only 10 people. I know what that high agility feels like, but then, there’s also the scale. We’re a global, almost $2 trillion asset manager. You can’t just make stuff up and move fast and break things. You have to bring those two thoughts together, and be really careful and thoughtful about what you’re bringing to the firm.

BRIAN

Well, along those lines, we’ve talked a little bit about speed and how much digital and technology in general has been changing along with this great bull market over the last almost decade. What I think is interesting is the technology or some of the experiences that businesses can provide is both a blessing and a curse. I spend a lot of time, as you know, leading my customer ideation labs, and that with certain companies. And the thing that a lot of consumers don’t realize is, an industry like yours, an industry like health insurance and a few others that are notoriously not great for customer experience, are also regulated in ways that I don’t think the end consumer knows. Sometimes, you’re operating within a small little area that you have to be in, but where there’s a disconnect with consumers is the smartphone allows you to do so, so, so much. The bar is so high now. Talk a little bit about how the customer experience bar can impact someone in the financial services at an advisor level. The expectations have to be sky high now.

AINSLIE

They certainly are, and I’ve always believed and held very dear that no matter what industry you’re in, the customer will always win. If you think that you can’t meet customer expectations, you better get ready for a declining business, because the customer will always win. They are the decision maker, the client is the decision maker, the end investor is the decision maker. And if they don’t like your offer, they’ll simply walk. And so, if firms are not accepting deeply that they have to go meet the end investor or the client or the customer where they are, they might as well just start getting ready for a declining business. And so, I think that even if expectations are sky high, you gotta meet them, because that is reality of running a successful business. You have to be customer-centric, client-centric.

And so, financial services, as you said, has been struggling, they are behind, it is highly regulated, but everyone has truly accepted deeply, that we gotta pound through a lot of those issues and get to clients at their expectation level and hopefully, even a little bit above because otherwise, our relevancy will just decline over time. It’s hard, no doubt, for all the industries: Health, insurance, finance, all heavily regulated industries. But there’s really no choice. We just gotta do the hard work.

BRIAN

And it goes back to something that you mentioned for just a brief second earlier. It’s a culture thing, too. I know I had the chance to hear a couple of the tales of your early days at LearnVest. And I know you said that it’s a little different of an animal, of course, but the mindset is, “We can do this, we can do this.” And inside some of these organizations, they have to realize… It’s exactly to your point of, we’ve gotta be able to exceed these expectations because the competition is so fierce and the expectations are so high, and if you stay the status quo, you’ll get eaten alive. That’s just the reality of the market, no matter what industry you’re in today. What’s one thing that an advisor could be doing to harness the potential that wealth tech provides him or her today?

AINSLIE

There are starting to be a lot of really good tools for advisors. The industry has caught up somewhat in the last five to seven years, and advisors are really starting to have things at their fingertips. What I think advisors need to do is to continue to focus on areas where technology could lever their practice and seek out solutions, and if they can’t find one, demand from partners that they help them create a solution. And partners, either being, if they’re in our network, working with that, or if they have asset manager relationships, working with companies like ours. But whatever the case may be, they need to see what’s out there, try it, and if it’s not working for them, demand more. And sometimes advisors are almost shockingly used to inefficient workflows, or not having information at their fingertips, and they need to take an outside-in perspective or really listen to new people as they onboard them into the practice, especially… Who’d say this? Young people, but young people who really are really facile and knowing how technology can lever and make them more efficient, and just have really high expectations.

Yeah, I guess it’s a little bit intimidating. There’s a lot to learn, there’s a lot to figure out, but it’s also this mindset that… Especially for advisors, if there’s any fee pressure, which there is, the only way to combat that fee pressure is to get leverage in their business to get efficiency and more effective workflows, and more effective leverage out of all the systems they’re using so that their margins are protected and their business is protected, and they can continue to serve clients effectively, instead of being scared and intimidated, they should be demanding and ask for more and really take this stuff for a test drive and see what it can do for their business, and if it’s not working, set the bar higher.

BRIAN

Great advice on that. I wanna come back to marketing for a minute. We’ve talked a lot about how digital can affect customer experience and the expectations of consumers today. We’ve had a number of CMOs on the Brand Lab Series over the last five seasons, and one of the things that’s interesting is, and I know you’ve seen this first-hand as well, is that a lot of times, the CMO now, he or she is being tasked with customer experience across the enterprise. That’s a whole other hat that he or she is wearing. Do you think that’s a fair ask? And what advice would you give for a CMO who’s actually new to the customer experience part of his or her job?

AINSLIE

Is it a fair ask? It’s a big ask, to be able to cover all of brand, user acquisition, lead nurture, all that stuff, and then carry it through the entire client experience. That is a lot of different things to do. If you have someone that can stretch it in that way, and that makes sense for the business, that’s great. Personally, it is oftentimes, at least today, still more productive to separate the roles and have CMOs focus on the front part of the experience, and partner with a head of digital or chief experience officer for the client, once they’ve become a client through to when they’re offboarding as a client, which is hopefully never, that whole part of the experience, because that’s a different ask. There’s a lot of workflow expertise, there’s a lot of journey expertise, there’s a lot of persona expertise, there’s a lot of deep, deep knowledge of how operations work, and when you’re trying to get friction out of a system, sometimes you have to go deep into the billing system that was originally… And I had this experience, it was originally set up in the 1970s to work in one way and modern expectations are completely changed and you have to go into the guts and reformulate it and bring it back out as something relatively modern.

That’s just heavy, heavy lifting. And for now, while… Especially in finance, I guess, that’s my perspective, while we’re trying to upskill in so many different areas, combining the role is really… It’s really tough and it’s a big ask, but in other areas, it might be a little bit different. It’s hard to have a blanket statement there, but they are different things, if you really think about it. And as I said, if there’s someone incredibly talented that can handle both, great. What skills do they need? A lot of operation skills, [chuckle] frankly, and if that person exists, fabulous. But for the most part today, I would still treat them as two very separate things.

BRIAN

I would actually agree with that. And I know a lot of CMOs, and sometimes, I’ve seen people that want to try to take on that additional responsibility. And the conversation always be careful what you wish for, because in general, the CMO life is not that long to begin with, and that’s a big job. And then, I think you nailed it, when I came to some of the operations experience and expertise, and I think that even the best CMOs are not maybe, classically trained that way, his or her experience hasn’t led them down that path, they’ve done other things really well. And it’s so funny, I’m gonna date myself here for a minute. But I think back to my early careers in technology back in the ’90s, and it was… All the technology went through the CIO. And now, you have a CMO that’s also grappling with the whole martech issue as well. And that’s a whole other skillset where I feel like it’s opened up a really big can of worms that makes the CMO job a really challenging one today.

AINSLIE

Yeah, and so, back to why I think they’re two big jobs and that they’re different. Getting the right martech platform and getting all the data talking to each other and really doing a really good job of operationalizing that is something I don’t often see done well. It’s like folks wanna skip the tech part of the job they have and wanna get into the tech part of the job that they’re stretching to and the companies would be better served if you just got really good at both things, which is really hard to do with one person stretched really thin. But again, my perspective.

BRIAN

For sure. Well, beyond marketing and customer experience and technology, one of the things I really admire about you, is that, you’re a sponge when it comes to leadership and knowledge, and you love to share a lot of that. You’re a great social media follow because you always have some good insights or sharing some interesting articles and things. Talk about your leadership style.

AINSLIE

It’s been the same since I was 25, and I’ve been coached many times to potentially think differently, but I’m an old dog. I have no new tricks. My leadership style is really to hire, I truly believe this, people that are smarter and more talented than I am, and then spend my days trying to figure out how to make their lives easier. I really buy into… What’s popularized now is servant leadership, which is the people closest to the work are the ones that need to have everything happening for them. And I’m not close to the work anymore, so my job is to work for them. And so, I absolutely abhor micromanagement. People should be given big mandates, big challenges, asked to rise to the occasion. If I ever get coached to dive into the details and micromanage my team, I won’t follow that advice, because I think it’s antithetical to developing great teams. I love to be on top of the business and know what’s going on, very, very different, so I can help, but it’s not about diving into anyone’s work, it’s about trying to get roadblocks out of their way.

It’s really funny. I just re-shared something I thought was really thoughtful about micromanagement online, and it was crazy. It got re-shared so many times, I think it ended up with almost half a million views and I thought to myself, “Wow. People must be really struggling with leaders that are micromanaging them, if they’re so invested in re-sharing this content.” And it just made me really sad, [chuckle] ’cause I’m like, “That can’t be… At least in my mind, that can’t be the answer. It can’t be the answer.” We have to give talented people big important meaningful challenges and let them fly. I guess, that’s the summation of my leadership philosophy, and that’s what I wanna see in the world from leaders, I guess, if I was to go real meta on it.

BRIAN

And it sounds like then, this whole philosophy… You even alluded to it, it hasn’t really changed, whether you are in a small business, whether you are in a startup, or in some of the big large-sized corporations you’re in, the style hasn’t really changed.

AINSLIE

No, it hasn’t. And listen, it’s a little bit hard for me right now. My team’s relatively small, we’re just, as I said, doing a start-up in a big company. It’s tempting to go in and wanna get deeper into somebody’s work and… Someone would call it “push pixels”. It’s tempting, ’cause you’re like, “Oh, you know, well… I could get in and do some stuff,” but you gotta pull yourself out of that and say, “That is not that my value, my value is to now go find the next big challenge for this team because if I just go and push pixels on the work they’re doing, I’m not serving them for 12 months from now, when they’re gonna want big challenges and something extra and more important to do so my job is to go find interesting work for them, not to get into the work that they’re doing incredibly well.” I don’t think it matters about the size of your team. I’ve managed five people, I’ve managed 300 people. The difference is, ask yourself, “Why am I here as a leader?” And the answer is, “Anything that looks like a micro-managing my team’s work.” Then I would ask, “Why are you getting paid?” Because you need to provide value in a different way, which is to unleash your team’s creative potential, and now you’re worth your money. But that’s my philosophy. I know lots of people see the world differently. I just can’t professionally see another path that works for me or my teams.

BRIAN

I do think there’s one thing that’s a little underlying, though, to make that environment successful, because if you agree with the servant leadership style approach, which I know many do, I do think there’s one element that does have to be there that’s unrelated to more the philosophy. And that is, at least, making sure that you have equipped and trained your people to do their job well. Sometimes, what I do see a little bit in more of the startup ecosystem is, you do come in with this mandate, and then you walk away and you expect everyone to be able to do it, but you haven’t actually quite given them at least some of the tools or training they might need to then exploit some of their own talents or their own points of views to then take it to a whole other level. And that’s where sometimes managers fall down, because then they think, “This person didn’t get it,” and it’s like, “Well, maybe they didn’t, but also maybe, you didn’t equip him or her with at least what they needed to take it to that whole other level.”

AINSLIE

Well, and I don’t think servant leadership, it for one second means delegate and walk away. In fact, I think what it means is, you are serving the person that’s working for you until they are highly productive, highly effective. If they don’t have the tools, if they don’t have the expertise, if they don’t have the concepts, it’s your job to teach, to coach. Really effective servant leaders are folks that have deep domain expertise. I can write a user story, I know how to write a [chuckle] user story. If push came to shove and I had to write three versions of user stories, I can do that. I don’t mind sharing that knowledge and bringing people up to speed, but what I don’t do is define my value as writing a user story. You have to be able to go in and help in all the ways, every single way, and tirelessly help in all the ways, but it doesn’t mean that that’s where you should stay. And I think that that’s an important distinction.

BRIAN

Absolutely. And you said something that just got right to me. You talked about the value… Your value is not in writing that. That’s the other thing that I always tell people, “Take a step back and see how do you add value to the team, to the organization, to the client?” I think that that’s super interesting, and I love the fact… I remember back in your early days at LearnVest, you and Alexa and others, you got certified so that you could walk the walk and talk the talk when it came to financial planning in and that. I can’t remember exactly what those details were, but you were making sure you understood what you needed to know to take it to a whole other level.

AINSLIE

Absolutely, and leaders can’t be above the work in a way where they aren’t incredibly articulate about the details of the work. When I say detail-oriented, it’s not about not knowing how to go there. You need to know how to go there, but as I said, you just… It’s not your job to stay there. I remember lots of times, coaching our product team, our financial planning team, at LearnVest, going deep into financial plans, finding small issues, and using those as examples, pulling way back and saying, “Listen guys, if we have this issue way down on page number 20, let’s pull it all the way back. And now think about trust and experience and what we’re actually doing for the client and you gotta go be able to find those teachable moments in some of the detail, but it doesn’t mean that you live there, as I keep saying.

BRIAN

Yeah, well, I’ve had the… To our audience that’s listening, I’ve had the pleasure to collaborate and work closely with Ainslie for almost a year of my life and I can speak to a lot of the truth that she says in terms of the experience. And there’s a handful of people… And I know we don’t ever get the time to talk very often, ’cause you’re a very busy moving person, balancing a lot, as am I. And that’s why I was glad I could get you on the show again, but you’re always sharing some good stuff. You’re a great follow on social, but it is funny how you took something like on the micro-management and it just got shared and shared and shared. And it’s like yeah, clearly you tapped into something there, and your leadership style, and we talked about a little bit in that first episode, years ago has always been something that I’ve admired. As we start to wind it down, I thought we’d shift for just a quick little fun speed round. We’ve talked about your role at PIMCO, your great evolution from a marketer to a technologist, how important the industry of financial tech, and wealth tech is to you. You’ve got great experience and insight obviously, on the customer experience side, as well. But I thought we’d play a quick little speed round. Are you ready?

AINSLIE

I’m ready, let’s do it.

BRIAN

Yeah, simple answers. I think I know the answers to a few of these, at least I’ve made some internal bets, so we’ll see. What would you rather watch, hockey night in Canada or football night in America?

AINSLIE

That’s so easy. Hockey night in Canada.

BRIAN

Yeah, I figured. That was my easy one. This one I’m not sure about: Favorite flower.

AINSLIE

Oh, easy. It’s a three-way tie: Lilac for the smell, hydrangea for the volume, and hyacinth because it is the epitome of spring.

BRIAN

Wow. I definitely got that one wrong. And if you don’t know, not only is she just this wealth of leadership knowledge, technology knowledge, Ainslie is a master florist. Is that what you call it?

AINSLIE

I guess so, yeah. [chuckle] As a mid-life crisis, I bought a flower shop, and taught myself how to be a florist but ended up selling it, it wasn’t my all time dream, but it was certainly a fun experiment.

BRIAN

When you’re commuting into New York City, what kind of music or podcast are you listening to?

AINSLIE

I’m obsessed with behavioral economics podcasts, all kinds of TED Talks and Dan Pink kind of stuff, and anything that gets us into the brain of folks making complex decisions is really where I love to spend my time.

BRIAN

I thought you’d probably lean towards that. This one, I’m curious about, ’cause like me, you and your family love to travel. What’s your favorite destination that you’ve been to.

AINSLIE

All of them? All of them. I think travel is just one of the greatest gifts that we have as a modern society and experiencing other cultures, other places, whether it’s simply going down to DC to see the cherry blossoms or as we did, go across the ocean to experience Morocco in the Sahara desert. I just feel so lucky, and I think travel is just one of those things that if there’s any way anyone can fit it in their life, just prioritize and do it because it’s probably the richest most important thing you can buy, if you like it. Some people don’t, but I absolutely love it. Any chance, anytime, anywhere.

BRIAN

Yeah, I’m right there with you. Is there a place that you haven’t been that is definitely on the list?

AINSLIE

Yeah, a long, long list. Gotta get to Southern Africa. My daughter just went to China with school and I’ve never been to Asia, so I’m deeply jealous.

BRIAN

You haven’t been? That surprises me that you haven’t been over there.

AINSLIE

You and me both. It’s just been a long list of other places. Yeah, I know, my daughter just got back from a public school trip for 10 days in China, lucky devil. Yeah.

BRIAN

Yeah, if you think the cherry blossoms down in DC are nice, wait till you see them in Japan.

AINSLIE

Can’t wait.

BRIAN

Yeah, how about a final one? Do you have a guilty snack?

AINSLIE

I’m salty snack girl all the way. Popcorn chips, tortilla chips, and I feel guilty for all of them, but I can’t stop. They’re amazing. Yeah, I can pass any sweet thing but salt, bring it on.

BRIAN

See, my sweet tooth will be the death of me. I’m so nervous about that. Some days I feel like I have this sugar addiction, maybe, because I can’t turn down like, “Here’s a new donut or here’s a this or here’s a that… ” But I try to avoid that. But then again, I just found myself last night eating a ton of peanut butter pretzels right out of the jar shamelessly.

AINSLIE

See, now, that’s my jam. That is… Anything… Yeah, that’s awesome. [chuckle]

BRIAN

Well, I knew that this would be a great and fun conversation. I’m so appreciative of your time, your whole team’s time, putting this together. I know that this will be a really great episode for our audience. They’ll really appreciate your insight and expertise across digital. I know we talked about the whole idea of digital transformation, which all industries, including yours and mine, are obviously trying to grapple with and get ahead of the curve and think about how they can build a great future for their employees and for their customers. I can’t thank you enough for being on. We were way overdue to catch up. I’m glad it took a podcast to do what we could. Ainslie, thanks so much for being on.