What If Tech Leadership Wasn't About the Tech? An Interview with Jennifer Baker

In this episode of What If? So What?, Jim talks with Jennifer Baker, former CTO of Synovus. She shares her journey from unexpected career opportunities to becoming a trailblazing technology leader in the insurance and banking sectors, culminating in significant strides in product development, customer experience, and digital transformation. 

Beyond her professional accolades, Jennifer passionately advocates for education and empowerment of women and children through her nonprofit work. Her story is a masterclass in continuous learning, adaptability, and crafting of a career full of diverse experiences, which she likens to assembling "puzzle pieces."

Hear Jennifer's insights on the critical need for mentorship and sponsorship to support women in technology, especially in a post-pandemic world. As a self-described "accidental CTO," Jennifer shares her journey embracing unforeseen opportunities and adapting in a rapidly changing digital world. 

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Chapters

• 0:05 Navigating Career Growth and Technology Leadership
• 11:52 Building a Diverse and Inclusive Workplace
• 20:56 Leadership in Digital Strategy Podcast

Transcript

Jennifer Baker: 0:05

I had a great mentor years ago when I was with AIG that said always raise your hand and always be eager to learn, and his sentiment was in every meeting. This was long before you had the Sheryl Sandberg book saying to lean in an meeting right Long before that.

Jennifer Baker: 0:20

is whole focus was you're never going to be the expert in everything, so be eager to learn as many things as you can. That will give you what he called this puzzle, and so every time you took a new assignment, it added a puzzle piece. Every time you were promoted, it was a different puzzle piece because your responsibilities and your role change.

Jim Hertzfeld: 0:39

Welcome to What If So What, the podcast where we explore what's possible with digital and discover how to make it real in your business. I'm your host, Jim Hertzfeld, and we get shit done by asking digital leaders the right questions What If, So What? and, most importantly, Now What? All right, I'm really excited in this episode to have Jennifer Baker on, and she's done a lot of things in financial services. She's a financial services expert. I would say a technology leader and has a story to tell around some of the nonprofit work she's doing. But, Jennifer, thanks so much for being on the podcast.

Jennifer Baker: 1:12

Absolutely. Thanks for having me. I have been a fan and I feel like there's some big shoes to fill, so I'm going to do my part.

Jim Hertzfeld: 1:18

All right. Well, it's pretty easy and you have a great story. I want to hear about it. But tell us a little bit about your background. What led you maybe not to this moment in your life, but what have you done in your career, kind of what drove you through it, what guided you through, what kind of got you here? I'd love to hear that background for everyone.

Jennifer Baker: 1:34

Yeah, absolutely! So. I've been in financial services, like you said, for a number of years. That was not an intentional decision on my part. It actually was the industry that I started with when I graduated college, and so I started as my first job out of college with a very large insurance conglomerate that everyone's probably familiar with in New York, where I was in their aviation insurance division, which seems nothing similar to the technology management degree that I have, but it was my first job, and so I had an opportunity at that point to learn a lot around the insurance product set. A lot around fractional ownership, which is very common in the aviation space.

Jennifer Baker: 2:11

I transitioned from there into another financial services organization, which was a top 20 bank, and so the roles or responsibilities there were around learning the retail banking space, obviously a lot around customer experience and customer journeys. While I was there, they purchased and did an acquisition of another financial institution on the West Coast, and so I had an opportunity to be part of their merger and acquisition team and do training and coaching for the state of California and the state of New Jersey, and then transition from there to my next stop in my career, which was another top 20 bank, and that was focused on product development. So, you know, for the purpose of your audience we refer to all of it as digital now, but it used to be called Omnichannel and it used to be called self-service and it used to be called all these other things. But when I joined them, I was focused on building out those self-service channels. So at the time it was defined as branch automation ATMs, your online, your mobile, biometric safety deposit boxes was a big one at the time when I was there, and so that was just sort of that idea of self-service. But it was always around product development, always around building on the customer journeys piece of it.

Jennifer Baker: 3:19

And then my last role, I joined a small community bank and was focused on their recruiter. When they reached out, said, hey, we're getting ready to do a similar journey and experience associated with overhauling their entire self-service channel set, and so they asked if I would be on board with it. And so I was eager to kind of put some things that I had learned in a fragmented fashion all together in one puzzle piece and be able to come in and deliver that from a product and a mindset and team building perspective. So that was kind of a little bit about the career and then throughout it, you and I have talked briefly, I was always really active in the nonprofit and volunteer space in the communities and it really started out as just I wanted to. It wasn't really a responsibility or anything that I thought I needed to. I was always drawn towards education and I was always drawn towards women and children, and so that really is kind of where I spend my time now, ironically, which is contributing to a number of boards that are focused in that particular space.

Jim Hertzfeld: 4:20

Oh, that's really cool. I mean, you've done a lot of different things. I wonder if you were like me.

Jennifer Baker: 5:01

I never had CTO on my list of my career aspirations at all, not for any reason other than I always viewed technology as an enablement tool.

Jennifer Baker: 5:11

It was a resource to me. So, whether I was in product development or whether I was managing a self-service channel, whether I was responsible for automating 300,000 aviation underwriting files, long before you had the term business process optimization, it was just the thing you needed to get done and technology was a tool for it. So, I think it was always just -it was always around my career. It was always a tool and something that I leveraged in order to be successful and to deliver on the objectives and the metrics that I was accountable for. But in my mind, it was always that traditional executive role. For those that were really passionate about engineering or really passionate about development, that was sort of the progression that you continued to go towards. And, so to me, it was never on my radar, because I was always on the business side, solving something different and leveraging technology and technology partners, but it was never without a traditional engineering and development background. That just wasn't something I was actively charging towards.

Jim Hertzfeld: 6:11

Candidly, yeah, I mean I think that's what most of us think about. You think of a CTO as sort of the chief nerd. You know I say nerd very endearingly as a nerd, no offense taken. But you know, I think your approach, your story, is kind of solving one problem after another, and the great thing about technology is we're always presented with new technology. There's always real- life business problems to solve, but it sounds like you really focused on the business and focused on getting stuff done, and is that sort of the approach. Do you think that made a difference in your career? Did you compare yourself to, maybe, folks with an engineering and development background, or did you just not even think about it and say, "you know what? I got a problem to solve, I'm going to GSD.

Jennifer Baker: 6:56

I was focused on the GSD. Honestly, it was always about whatever the problem in front of me was and what are my options. I had a great mentor years ago when I was with AIG that said always raise your hand and always be eager to learn. And his sentiment was in every meeting. This was long before you had the Sheryl Sandberg book saying to lean in in meetings right? Long before that.

Jennifer Baker: 7:18

His whole focus was that you're never going to be the expert in everything, so be eager to learn as many things as you can. That will give you what he called this puzzle, and so every time you took a new assignment, it added a puzzle piece. Every time you were promoted it was a different puzzle piece because your responsibilities and your role change. Every time you were tasked with a different project or a different product or service that you needed to bring to market, his lens was always as another piece of the puzzle, and so, ironically, I have kind of a funny story around how my puzzle ended up in a CTO role that I'm happy to share, and that is I had my boss at the time. He came to me and he said I want to blow up the technology team, and at first hearing that I thought I'm not sure I'm on board with that. I don't know what that means, and so certainly there was a lot of discussions that took place around it. What he meant by that was building out results over recognition and a KPI, business-minded business unit, and so where that stemmed from is the team at the time before I took over had built out really a maybe I'll call it an IT black hole. So they would interact with the lines of business, they would get what they perceived to be the requirements, but the solution was really whatever the path of least resistance was for the technology team to deliver, and so oftentimes that would create a little bit of friction between your lines of business and your technology teams, because that's not exactly what I thought it was, and so unfortunately, there hadn't been a lot of focus and time from the technology team perspective to say help me understand your product, help me understand your line of business, help me understand where your pain points are and help me understand what do you define success as? Because oftentimes, once you could start those discussions, they would tell you what they needed. You didn't have to be this epiphany of you know Albert Einstein that came up with what their solution was. They knew their business.

Jennifer Baker: 9:15

So there was some comfort, and that was, I would say, probably a difference in the approach that I took, which was I was never going to know all of their lines of business. I wasn't the subject matter expert coming to them, but I was coming in to say, hey, I think my team that I'm responsible for has let you down and I think that we can build something better. Can we work together? Tell me what's broken, tell me how that feels like and focused on the internal customer dynamic of it. And that's really what he was referring to when he said blow it up.

Jennifer Baker: 9:45

It was moved from a delivery team that didn't really understand the whys and the hows and the products and the services and the growth objectives. It was just I'm gonna deliver something that I deliver to you. And so the minute that we started making that shift internally from technology- centric to business- centric and technology was a piece of it that was going to help us do it, it started to get a lot of people on board. There were simple things that we put in place.

Jennifer Baker: 10:13

We did scorecards here's how your line of business leverages mine, here's the number of people that call, here's the top three largest platforms and consumption of them. And when you start feeding all of that information to say with full transparency, I don't know how we're going to do this, but I can tell you that this is how we interact between the two teams. Right now, a lot of the barriers and a lot of the walls start coming down to go. If you can help me make my goal. I'll help you and plug you in any meeting that you need, and so I'm learning their business, but they're learning the technology business, and the common thread throughout is every business leader wants to have growth, whatever you define growth as so it was painstaking, but it was necessary to add a different lens to it, because you can't blow it up and keep everything intact.

Jennifer Baker: 11:02

You got to be aggressive with what you blow up.

Jim Hertzfeld: 11:05

Wow, there are about 10 stories in there, Jennifer. I'm hearing like a leadership story. I'm hearing a measurement story. I'm hearing a change management story. Gosh, the thing that stuck out to me I'm just thinking your situation and similar situations. I'm thinking of situations I'm in where just getting everyone sort of rowing the same way, right, or rowing in the same direction. So, we could probably dig into that for a long time.

Jim Hertzfeld: 11:27

But you said a couple of things that upfront it kind of really stuck out to me. First, the puzzle. From a career perspective, you're building a puzzle about your life or your career, right? You don't even know how many pieces there and it just sort of happens. But again, as long as you keep going and add the puzzle pieces, it'll eventually make sense, as long as you keep adding the puzzle pieces. There's a great metaphor in there I hadn't heard before.

Jim Hertzfeld: 11:52

You talked about outcomes. I think it's such a great way to get teams to think about technology differently, because I've seen this. I've been in technology for 30 years now and we're all enamored by the technology. I think that's the biggest problem with technology. We see the easy button or the pixie dust, like AI. We can talk about AI forever on this one, right? Oh my gosh, the AI is going to do it. This is finally the solution I've been looking for. So I love that focus on outcomes.

Jim Hertzfeld: 12:18

I heard a story recently about being busy as being the new procrastination, which is counterintuitive. But people stay busy. They like to stay occupied, but they're actually kind of procrastinating something else or putting something else off. And that focus on outcomes make sure you're busy on the right thing. So gosh, so much in there, Jennifer, in that story. But I kind of build on that puzzle piece because I think you said you didn't really set out to become this technology leader. You didn't know that that was a piece in your puzzle and so you were sort of an accidental leader, potentially right, maybe an accidental role model, and that's something I know we've talked about before. But yeah, I've looked up some of these statistics and, by the way, my daughter is two years into her IT career, so I'm very proud of her.

Jennifer Baker: 13:05

Fantastic.

Jim Hertzfeld: 13:05

And so I'd love to hear these stories and translate them to her and, by the way, I'm going to keep going back. I'm going to see her tonight. I'm going to tell her about the puzzles.

Jennifer Baker: 13:13

I love it. I love it.

Jim Hertzfeld: 13:14

But I looked this up - women make up only 25% of the tech workforce, which is, I didn't really know where that stood. It's a little lower than I had expected - 11% of executive roles and only 8.3% of CTOs are women and that, you know, the numbers just getting worse and worse as we dig in. But you know, I think that certainly creates a lot of challenges. Maybe you were just too busy, gsd, you know to care, but you know I'm conscious of those challenges for my daughter. But I think it becomes a challenge for companies and then the customers that they serve. I mean, I'm trying to be an ally, but help me out. What challenges do you think that creates for our businesses, for our society?

Jennifer Baker: 13:58

Yeah, before I kind of jump in on that, I might make just an interesting point and that 8% as female CTOs has been that number or close to it.

Jennifer Baker: 14:07

It will go up a little or down a little. It never really moves dramatically. So, when you couple that with I just looked at the 2024 McKinsey Women in the Workplace Study, that is, we're not really moving and progressing with our internal ally and DE&I efforts enough to offset what's happening from an economic standpoint. We all know it's very well publicized we lost a lot of women in the workplace with the pandemic for a variety of reasons. Right, Work-life balance was one of the bigger ones if they had children. You now look at that study in 2024, now, years later, post-pandemic, and an interesting tidbit on this year's survey is that it's middle management that predominantly at the female level was lost. So, think about that for a second. If that 8% at the CTO level has been that way for a good portion, you've now lost women overall across all job roles and segments and categories and tiers in the pandemic. You now are coupling that, you're losing this middle tier. From an ally perspective I would say get out and get involved. You know you're doing your part with your daughter and making sure she's got opportunities. Is she connected? Is she talking to her friends? Is she in forums and associations that are focused on infusing as many women at every level into the workplace as you can? Because that middle tier, sadly, was our future senior tier and our future C-suite tier. Kind of an interesting and scary aha moment is that if you don't flood enough volume into it with having very tailored and very structured and very intentional programs to nurture women throughout that life, career, life cycle, you're going to continue to see at some segment every report's going to have some diminishment.

Jennifer Baker: 16:00

So I just think it's it's helpful context. I know that from being in the CTO space. You know that as a result of looking at the study. But I think it's helpful context. I know that from being in the CTO's phase. You know that as a result of looking at the study. But I think it's interesting for your audience and your allies to recognize. It takes everybody. You need more hands, you need more intentions, you need more programs, you need more sponsorships, you need to be willing to do mentorships. It's going to take everybody.

Jennifer Baker: 16:31

But I'll tell you just you know to answer your question around what the challenges are. It's kind of stating the obvious, Jim, like every survey that you read, regardless of who sends it out, the fewer groups that are represented in the room, it limits the perspective of the innovation and the design itself. It doesn't take me or you or anyone else to say that. It's very well known, very well documented across a variety of different studies. What do you do about it? Is what's different.

Jennifer Baker: 16:50

So are you mindful in the meetings to say, okay, we've got only one demographic showing, we've only got you know? I can give you a simple example on IVRs, we only tested in one capacity male voices that had a Southern dialect. So then when you move to voices that had a Southern dialect, so then when you move to a female with a Southern dialect which I try to hide, mine it comes up in a different result and different testing. And so it's things like that that you'd have to be intentional about it. So, whether it's in a meeting, whether it's who's represented in the meeting, whether it's where the ideas come from, where the funding goes, you've already got a talent shortage associated with it. You've lost so many women in the last several years for a variety of reasons. What are you doing to infuse more talent into the pipeline now, at every stage, so that they can be the next generation of middle managers or executives?

Jim Hertzfeld: 17:43

Well, the phrase that stuck out to me in that report was they call it the broken rung right, and that clicked with me right away. And if you see this report, there's a series of graphs. You can just see it. You can see where it's flattened out and there's trend lines, which I love to see those. I think we have to see the progress right. Progress isn't parity, but you're really digging in on something I think we both love - getting (bleep) done. Honestly, it's sort of the genesis and sort of the inspiration for this podcast, to leave on something we can go do right now. And so I appreciate all you’re doing, and it’s always helpful for me as an ally, to be mindful. I was at a dinner last night with a colleague and former co-host of this program. And we both looked around and said “yeah, you’re the only woman here, what do we do about that?” And we always talk about it, so I appreciate what you’re doing. Maybe one thing our listeners can do, and I think you’ve given a lot things around getting involved and advocating, but maybe someone who’s listening to this and in technology or interested in technology, or digital. What would you leave that the listeners could do right away to make a difference.

Jennifer Baker: 18:50

Oh my gosh, start focusing on. If you don't see it, be it. If you have an opportunity to be in the room, be a voice in the room. Don't sit there quietly. If you don't see representation on a leadership team, ask about it. Become it. Volunteer to be part of it, if you don't see it, there are so many great organizations that, you know, I'm on the board with Women in Technology, so I'm super passionate about that one. But there's so many great associations or forums that you can look into and be a part of that.

Jennifer Baker: 19:18

Start to build a network in a safe space. You're going to have similar topics, might as well have a group of empowering people that can help you build your puzzle the way you want to build it. So I would just say it's kind of my go-to is GSD. Just get it done. Start somewhere, even if it's small. Even the holidays are coming up. Start in your holidays. Do you know what your neighbors do? Do you know what industry they're in? Do you know if they're open for mentors? Do you know all of those things that you can start to build a network and start to nurture that network long before you need it. I think that's another big one as well. Be really diverse and really broad stroke in how you build and who your tribe is. That's a common one in the women world. Mine's called band practice. I just didn't care for the word tribe, so I've heard it called your board of directors.

Jennifer Baker: 20:06

So be really intentional when you surround yourself with your personal board of directors. I've heard tribe. That's a common one. We do band practice. I'd love to tell you there's a great answer for it. We just thought it was funny and it stuck.

Jim Hertzfeld: 20:19

So that's a good one.

Jennifer Baker: 20:21

Yeah, we just that's…so when you need a good gut check, that's a really great safe space. If you've been nurturing that along and choosing intentionally people that are in future roles or future companies or similar backgrounds, so that you can talk through the struggles and opportunities a little more candidly, because they've got some similarities, it's not, you know, you've got a partnership and a collaboration that's already been built before you start looking to expand.

Jim Hertzfeld: 20:47

Well, that's good. That's very actionable. You give us a lot to think about. Like I said, you get about 10 stories in one, a lot of visuals, a lot of metaphors, a lot more to talk about, but we're out of time for now. Jennifer, thanks so much for being with us and sharing your story and for being not just the accidental CTO, but the accidental role model.

Jennifer Baker: 21:04

Well, thank you. Thanks for having me. I've enjoyed it.

Joe Wentzel: 21:07

You've been listening to What If. So What? A digital strategy podcast from Perficient with Jim Hertzfeld. We want to thank our Perficient colleagues JD Norman and Rick Bauer for our music. Subscribe to the podcast and don't miss a single episode. You can find this season, along with show notes, at Perficient.com. Thanks for listening.