Inspired Execution

Chet Kapoor:

Welcome back to the Inspired Execution podcast. Each episode shares the experience and learnings of a world-class leader on their journey to success. The guests on this podcast are bold, brilliant, and not afraid to change. As you navigate your own path, we hope you feel inspired by their stories, lessons learned, and the vision of the future.

Today we are pumped to have Cindy Stoddard on the podcast. She's a CIO at Adobe, and as held leadership positions at massive companies like Safeway and NetApp. With decades of technical expertise, incredible business savvy, and an inclusive people-centric approach, Cindy is a triple threat in the industry. We discuss the importance of empowering people using AI as a co-pilot at work and operating like a cloud company. You're going to love this episode. Cindy, welcome to the podcast.

Cindy Stoddard:

Glad to be here, and it's great to meet you.

Chet:

Absolutely. So you have led tech teams at Safeway, NetApp, and now Adobe. What's been the magical moment on the journey? Like obviously many, but what would be the one that sticks out?

Cindy:

Yeah, I can definitely talk about the magical moment. I've thought about that, and there have been many if I think back in time. But I think what's happening now is that technology, IT, is actually recognized to be a core part of the company's infrastructure and transformation and innovation. And I think that's really, really important because CIOs and technology groups can see what goes on across the company. And I think that knowledge and that insight is finally being recognized. And I would say that the real magic moment happened actually during the pandemic where it was recognized that you can't do business and you can't run a company without that technology infrastructure in place. And not just the technology infrastructure in place, but a technology infrastructure in place that's actually digital and flexible and allow people to be anywhere and still be productive. A lot of companies actually struggled during the beginning of the pandemic trying to get their processes and everything set up.

We did really well, and just being totally transparent, when we clicked over on that magical weekend, I went to my office here to look at email the next morning and I expected to get a whole bunch of hate mail. "This doesn't work," or "We want to do this." I mean, you know the whole routine with technology, especially with engineers, "I do it this way," and blah, blah, blah, blah, blah. And I didn't have any hate mail. I had, "This is great." A lot of questions. We had set up a Slack channel for people to collaborate. There was a lot of activity going on. We could see that people weren't doing their normal things, but what they were doing was looking at Slack, looking at the knowledge base, trying to get comfortable. But the way that people came together and the questions that we did get were ... there were serious questions about uploading different pieces of product.

"How am I going to do it?" Because they're big and that sort of thing. And, "Did you think about that with the network?" And stuff like that. But I think that was the real aha moment was understanding that I would just say kind of finally, technology is being recognized as being really important in running a company. And then also that the investments that some of us as CIOs pushed for collaboration tools really did pay off, really did pay off. And I had a little second aha moment during the pandemic too, which was, and you probably know this from all the tech companies that you've run and been involved with. The normal process is you start with RFI and then you have RFP, and then you do a POC and a this and a that and everything. Well, we had problems to solve and we couldn't do all of that stuff.

Empowering the team to say, "Here's a problem, we need to solve it." And they went off in a fraction, like a real fraction of the time and solved the problem and solved it to what would be a mission-critical type solution. I mean, we had interns, we were very ... Adobe was very committed to bringing on interns in the summer. "But how did you do that?" You couldn't bring anybody into your office all over the world. So we came up with a process and a technology solution to facilitate that worldwide. And that's because you empowered people and you trusted them, right? So I think those are the two kind of aha and magic moments that I had over the past seven years here at Adobe.

Chet:

That's awesome. Now, I've always said, and I think you would agree with this, that digital transformation started around mobile, right? I mean that's when it actually started, but the thing that accelerated digital transformations the most, obviously cloud helped a lot, mobile cloud, but COVID, the pandemic was just like boom, right?

Cindy:

That's right.

Chet:

And recently my thesis has been that AI will actually accelerate cloud as well as digital transformations like never seen before. I think it'll be even faster than COVID or pandemic over a five-year period. Would you agree?

Cindy:

I totally agree. I totally agree. I mean, just look at what has happened with AI in the last few months and the different types of solutions that are emerging and the way that we can put it to work in our different environments. Adobe has had AI and products for quite some time, and you've probably seen some of the new things that we have out with Firefly and the power that it brings to the creative. We've been using it internally within my organization for some time also. We started actually pre-pandemic because we wanted to look at how could we make operations, I don't mean operations internal, but our cloud operations or computer operations network, all those types of operations, more effective. And we empowered a team to come up with a solution to say, "How do you get the mundane work out of the stream?"

And they came up using open source with a self-healing framework, and then they empowered that with AI and it's used internally all over the place now within Adobe for a number of different solutions. That's that. But that took a while to put together. Now when I look at the speed of what is happening and how we can enable our business processes and not just business processes with things like RPA, but helping people have a second brain or a helper, a copilot along the way to say, "Hey, I'm working on this particular thing, can my copilot do some of the work for me and deliver me back some recommendations or different options to look at and then I can take it from there versus trying to do all that individual research myself?" When I think about the opportunities and where we can apply it in the workforce, helping the workforce, helping business process, helping efficiencies out, it's endless.

So I totally agree with you and you can hear probably the excitement in my voice here because I think it's going to be the next generation. I'll just kind of digress and say a lot of people are talking about, "Well, is it going to change entry level jobs and things like that?" And I've said to people that they should actually take a journey through the technology museum and think back in time. I mean, back in time with mainframes and things started, there were punch cards and trays. Would we really want to be doing that job today? Probably not based on what we have here. So I think we've gone through different evolutions in technology where how we work is going to be significantly different, but that significantly different is significantly better because it allows us to use a higher order skill in order to make those contributions to our company, to society, to a number of different areas.

Chet:

I think there's a mic drop moment right here. I should not say anything. That was perfect. Thank you. Thank you very much. That was awesome.

So let's talk about people. I always think running a business is about three pillars. Different people have different frameworks. Mine is about strategy, people and operations. I've been using it for many, many years. It seems to work. So if we can focus on people, obviously people are the greatest asset. A lot of people can do strategy, a lot of people can operate, but people is what makes it work. And you've been an advocate for people-centric leadership. What does that mean?

Cindy:

Yeah, I have been. I have been. And I think that my style actually fits quite nicely with the Adobe culture because Adobe believes that people are most important assets. Adobe also believes that innovation can come from anywhere in the company. Interestingly, when I joined Adobe and I started working with my team, the team that I have now, they wanted to know what kind of changes I was going to make. And I had told them that I'm not the type of leader or CIO that comes in with a playbook that says we're going to do A, B, C, and D. That changes need to mesh with the organization, need to mesh with the business objectives and the people and a whole bunch of different attributes. So I spent a lot of time listening to people and understanding what the challenges are, what they wanted to be, and then actually put together a cross-functional team with individual contributors all the way up to people who would be my direct reports.

And I was pretty clear with them that I was not going to be top down in what we wanted to do. That was very important for us to co-create the future together, figure out who we wanted to be as an identity, and we do have an identity that we've put together and how we wanted to operate and what those behaviors were important for us to operate as a team. So I think that my style is one, to be people-centric and bring people together. That's not to say with the role that I have that sometimes you need to be directive and top down in certain types of situations, especially if you're having a problem going on at a particular time. But it's really important to build relationships throughout the organization and with your peers and across, foster those connections both inside and outside of the company as a leader to really embrace new ideas, not just be close mind and this is the way that it's been done, but really embrace the culture of curiosity and big thinking, and encourage people to do the same.

I love the interns that come in because they're just so open-minded. And yesterday I had a conversation on the elevator with an intern. I mean, it was great. They were telling me how excited they were and that they were working in digital media and this is going to be the best experience in their whole life. And that's what you need is you need to embrace those new ideas. And then be empathetic. Put yourself in other people's shoes and understand how they feel. And you need to take that in account as well.

Chet:

I love the energy of interns, so I think a hundred percent agree. All the things you talked about, the things that what you would call people-centric leadership, how do you assess them in the hiring process? Because not everybody's born with those things.

Cindy:

No, not everybody is born with those things. I think when you go through the hiring process and bring people on board, it's important to get to know them as a person, not just for the role that they're interviewing. You can interview without getting too personal, but understand how people think about different situations, how they have solved problems in the past, what they might be comfortable with or maybe not so comfortable with. How far are they willing to risk going out on a limb with a particular idea? So you can kind of probe and test for those types of things by talking about past experiences and not just what they've done in school or in their roles, but what they've done outside in different types of activities as well.

Chet:

And this is going to be off subject, but I tried really hard in my interview process too. We all have childhood issues and I always try to get to exactly what the childhood issues people have and have an assessment of it because that's ultimately what either drives them or holds them back.

Cindy:

Exactly.

Chet:

Everything else is a representation of those things. And so finding 18 different ways to find that, exactly what the issues would be, is probably the best thing that we could do.

Cindy:

You're absolutely right. And yeah, it's down to asking questions, same questions in different ways to understand exactly what that point is, but I totally agree with you.

Chet:

So one of the things that I find that is very hard, and I'd love to get your perspective because Adobe fosters such a collaborative mindset. How do you get people to think about outcomes versus outputs? Because there is a mix between collaboration and execution, and obviously you can do both, but you don't want to spend too much time doing collaboration either.

Cindy:

Yeah, so one of the things that I've said very clearly, put yourself in the shoes of the customer, whoever that customer is that you're working with. If you're in CloudOps, it could be the external customer and the services that we're providing to them. If you're internal, it could be a finance user or whatever. But the experience that you would want to have if you were in their role is the experience that you should try to provide to them. So treat them as a human. It's this empathy and making sure that people understand it. The other area is setting a vision for the group as well. When I joined and started the identity work with the group that I have, came up with this tagline called "we want to have cloud-like characteristics in our DNA". People at first wondered what that meant, and they thought it meant we want to run our environments like clouds and things like that.

But I explained to them it doesn't mean just that. That's one aspect for sure, but really what the driving force was is we want to be easy to work with. We want self-service. We don't want to have a line waiting to get into IT for changes and things like that. How do you think about having those cloud-like characteristics? And it all starts with the individual and their particular chair and who they work with. So you start with your peers within your organization and then you go all the way up until you hit the end customer, and people really understand that, and that is really focusing them on the experience and the output versus how many tasks did I complete in a particular day. So that's what we had focused on and we recognized people for their behaviors at my all-hands quarterly, and it's been a really great way to change how we have the different behaviors that we have internally.

Chet:

One of the questions I have, and you talked about cloud-like, right? You've always said hybrid work is a little bit like that. What is the one tip for operational excellence that you have in a distributed world?

Cindy:

One tip? I have a few, but I would say-

Chet:

All right, let's go through a few.

Cindy:

The one tip is making sure that your employee experience really meets with the persona of who's doing the work. I think there's a lot of organizations that try to do one size fits all for a variety of different reasons, but when you look at the makeup of a company, different work needs to be done in order to make that company move forward. You have people in marketing that are communicators. You have people in finance that are doing massive spreadsheets, analysis and forecasts and things like that, and then you have the engineering groups. To think that all those different personas could have the same way of working, it's not going to work. You're not going to be productive, you're not going to have happy employees, and therefore they're not going to be productive. So for me and my organization, we actually centralized everything that touches the employee into one organization, and then we look at the personas and we have toolkits based on the persona of who's doing the work, not a toolkit that would be mass distributed to everybody, but based on personas so that people can be productive.

So I would say that my one tip, my first tip, my one tip would be look at it through the persona view and don't try to force fit everybody into the same type of toolkit because it's just not going to work. I think you could have more productive organizations by catering to the needs of the different personas that you have. My second suggestion or tip would be to experiment. Just don't assume that you can do a POC on a piece technology in a lab and you're going to bring it in and it's going to work perfectly for those personas. What we've done is we created Lab82, which is named after the year Adobe was born, and we experiment with different technologies, and when I say experiment is we have people, we have engineering groups, we have finance groups come in and use the technology to see what works and doesn't work. And we have found things that just won't work and we haven't deployed them.

It's a great way to understand the working habits of people and then also see what technology investments would pay off over time as opposed to going through a traditional POC, running it out and then finding out that nobody is using this particular feature in a conference room because it really doesn't work for anybody. That's what I would say would be my two tips.

Chet:

Very insightful. You're a mentor for women in tech. What do you wish you knew when you were starting your journey?

Cindy:

I had a mentor who said, "Don't become a mushroom. Mushrooms live in the dark." What he meant was, you're now promoted to vice president, so keep in touch with the people, individual contributors, everybody in your organization, because they're the ones that have the pulse on everything that is going on. And I totally agree, but what I wish I would've known before that period of time is really what I tell people now is build relationships. Build relationships inside the company. Build relationships outside of the company with networks. Let people know who you are, not just for the role that you're in, but who you are, where you grew up, something about you, because that helps shape how you work with people and get people to know who you are as a holistic individual.

Chet:

And I think a lot of people feel that they don't need to be vulnerable, they need to hide their personal side because they're a professional person. And I love the show up as a holistic person, not as this is the professional version of me, that's all I'm going to show. Because getting to know the entire person will actually help your career.

Cindy:

That's what I feel. I've shared it with a number of people that I mentor. I've been involved with different organizations to help women. I've given talks. I sponsor this grammar school from the UK, from London, Townley Grammar School. They come to the Bay Area every year minus the pandemic, they're grades nine through 11. We mentor and talk with those girls to give them idea of what a career in tech could be. And again, it's about who you are as an individual, and that holistic, creative, if you have the creative background in yourself, can be used in many different ways in order to make contributions to your company, to nonprofits. I've been part of a nonprofit, started a nonprofit with a few of my other friends here in East Bay. All of that can come to fruition if you share a little bit about yourself.

Chet:

I have always said that leadership is about the best version of yourself showing up. Would you agree with that?

Cindy:

Yes, I totally agree with that. I totally agree with that.

Chet:

And I think it starts from leading yourself before you lead anybody else. Have you seen that through your career? Because you started ... It's not like everybody starts as a CIO or a vice president, right? You were an individual contributor, you became a manager, then you became a leader, and now you've been doing this phenomenally well. Any insights on how people make that transition and think about leading themselves?

Cindy:

Yeah, I started ... Absolutely, I didn't start as a CIO. I started as a programmer trainee at the Travelers Insurance Company at Hartford, Connecticut. As you move up into the different roles, I've always observed people around me and I've tried to see what they do and how they operate is I read a lot. So I read different books and to stay current, I used to read a lot of ... I still do read, but when I was coming up the ranks, if I saw technology I was interested in, I'd read and study up about that technology in different things in that area. So I think the way that you prepare yourself is to become very well-rounded. I also tried a lot of different things out in the technology fields. So I think that just learning about yourself as you go up the ranks and keeping kind of this inventory of what I like, what I don't like, this is what I'm good at, this is where I would like to learn more, is really how you become that holistic leader, and then spend time with people.

Spend time with people. I have an open door policy and I've always encouraged people to come in and just introduce themselves to me. It's been great to learn about people. I have to say that every one of the meetings that I've had, I've learned something as well.

Chet:

So now we're at the rapid fire part of the podcast.

Cindy:

Okay, rapid fire.

Chet:

And so I'll ask a bunch of questions. What's a ritual you do every day?

Cindy:

So every day I take a walk. I start my day by taking a walk with my dog, and it's an amazing way just to clear your mind, get fresh air, appreciate the outdoors and nature and beauty and the bugs and animals running around. So that's what I do every morning.

Chet:

If you had a theme song, what would it be?

Cindy:

My theme song would be What a Wonderful World by Louis Armstrong.

Chet:

That is sweet. That is sweet. If you could instantly master a new skill, what would it be and why?

Cindy:

Yeah, that's a great question. It's swimming. I can't swim. I'll share that. I can't swim, so I have made a goal to actually really learn how to swim, otherwise I'll continue to paddle around in our pool, but I'm going to learn to swim this year.

Chet:

That's awesome. That's awesome. What's your proudest personal accomplishment?

Cindy:

My proudest personal accomplishment is my two daughters, Katie and Emily. They're both very special in very different ways, so they're my proudest accomplishment.

Chet:

One word or phrase that describes great leaders.

Cindy:

I think it's empathetic, right? I've always said, put yourself in others' shoes. And I think that's what empathy is. You really have to have that to be a great leader.

Chet:

One word that you would use to describe yourself.

Cindy:

Humble, I think.

Chet:

Thank you. Cindy, this has been awesome. It's been a blast. We really, really appreciate you coming on the podcast. I think the listeners are going to have a lot of fun listening to this particular one, and I actually think we'll have to have you come back again, because I think I could go on for an hour talking about everything you talked about. So again, thank you very much for your time.

Cindy:

Yeah, no, it's been wonderful to be included in this. Thank you so much.