Women have so much to offer in the IT space. Nevertheless, the industry’s leadership is dominated by white men, making diverse culture a seemingly impossible goal. Asmita Puri explores how to change this with Nichele Dudley of VGS. Nichele shares her journey from Apple Genuis to Director of IT, opening her eyes to the important role of women in the IT industry. She explains how the DEI conversation must not be treated as a checklist but an actionable mission, pushing C-suite leaders to do something to create better workplace cultures. Nichele also discusses why people must not be treated akin to plug-and-play technology and how to make IT leadership opportunities more accessible to everyone.

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Building A Diverse Culture In The IT Space With Nichele Dudley

Nichele, I'm glad we are getting to do this. Thank you for taking time out of your day to talk to me about your career and share your story. I appreciate it.

Thank you. What you're doing is awesome. I'm happy to be a part of it. It's important. Thank you for even starting it and giving me a reason to come on and have a conversation.

Let's get into it. Can you share your journey from Apple Genius to Director of IT, where you are now?

Apple Genius was an interesting one for me. I was in high school. I had no idea what I wanted to do. It seemed like everybody else had their plans. They're like, “I'm going to go to this college. I'm going to figure this thing out.” I'm like, “Did I miss something? Was I absent on the day that people handed this stuff out?” I always loved Apple. Their products and technology are awesome. This was pre-iPhone. They hadn't even released it yet. I applied and had my interview. I was nervous, out of high school. I'm like, “I know how hard it is to get into Apple and work there, even at the retail level.” I got the job and became a genius there.

Have you ever had that experience where you do or experience something, and something in your brain unlocks? You're like, “This is cool. This is awesome.” I went to Genius training and did the whole thing in Cupertino. I loved everything about it. I loved people coming to me with problems and me being like, “Let's figure this out. Let's fix this. How are we going to do that?” It became one of those jobs where I was like, “This is cool. How can I do this forever?”

I was young. I was eighteen out of high school. I was like, “I'm going to work here forever. This is perfect.” As it happened, it started to become monotonous. I was like, “I wonder what else I can do? What is this role like?” I started to look online, mainly on Craigslist, because I had no idea. I was still young. I had no idea what resources were out there for job searching. I knew nothing about LinkedIn. I didn't know any of that. I looked on Craigslist. I was looking for computer jobs, help desk, and IT jobs.

I was able to find an ad agency in LA. They were hiring for a help desk. They were small enough at that time when they posted the listing on Craigslist. It was cool when I had the first interview. It was one of those things where I was like, “I'm excited. I hope I get this job. I don't have that much experience, but this would be great.”

I got the job. It was amazing. It was such a fun experience. I started there when they were a young company and less than 100 people. I learned and was learning so much there. It was great. That was where I started to climb the ladder by working at that company, getting promotions, and being like, “I've been here. I've been doing this thing. What else can I do? How can I grow?”

Fortunately, I had an awesome mentor that came in. When he first interviewed and was hired as the director of IT, he was speaking with his employees. I was having a chat with him. Everything is broken. This sucks. We need to fix these things. You're in for it. I'm ready to quit. He was awesome and gracious about it.

He took it as like, “Challenge accepted. You're smart. I can see that you have good ideas. You might need a little polishing and direction on how to approach this and where to go.” He took me under his wing and started to teach me the business side of what technology and IT were, why things happened the way they happened, what that meant, and why we couldn't do this thing. We needed to have the budget. All of those things didn't make sense to me.

He would throw problems at me. I remember the first problem he threw at me was getting jammed. We talk about it now, and he was like, “I gave you that problem thinking that you would shut up and you wouldn't bother me for a year.” Spoiler alert. It is not what happened. I came back to him a few weeks later and said, “I got the basic things set up. I already have some machines enrolled. They are reporting. He likes to make this do what we want it to do. To get the most out of it, I need to learn how to script.

He had this look on his face. Both are great because he'd implemented this before. He had run teams who had built this before and done this. He knew. He was like, “This takes a while. This isn't an easy thing.” I came back. I’m like, “I did the basics, but to make this work for what we want, I need to learn how to script and do this.” He's like, “My plan wasn't going to work for having you go away. Let's get you to get you on training on scripting to build this thing.”

It was when he realized that there was something there, and he took that additional time to say, “You get this. Let's figure out how to grow you. I'll mentor you.” We had those serious conversations like, “What do you want to do? Have you thought about it?” I was like, “I want to do this.” I saw him work for a little bit. I was like, “I want to do what you do. I want to move to New York at some point.”

He made all those things happen. I had the job that he had. The ad agency opened an office in New York, which I got to help build. I was able to move there, open that office, and run it from a technology perspective. Honestly, I owe a lot of my career and my growth to him. He was such an amazing influence. I got my leadership style by learning from him. The fact that he wasn't worried or scared about me saying, “I want your job.” He was like, “Let's figure that out.”

I hear you on that high school front where we're expected to know what we want to do next. It's like, “No, I'm a baby. Please stop asking me what I'm supposed to do with the rest of my life. That's too much pressure. I don't know.” In my 30s, I don't know what I want to do. I had a little bit of an idea, but it changed.

For the last several years, we've had everything laid out for you. Here's your schedule. Here's what you have to do. Follow this now. I was like, “Okay.” They were like, “You're on your own. Nobody's going to set a schedule. You have to figure it out.” I was like, “What?”

I hear that Casey, your mentor at your job after being an Apple Genius, had the impact that he had on your career. You're a fierce advocate for women in technology or women with diverse brains and personalities. I hear that impact that. Does that ring true to you? How do you see his allyship affect how you advocate for yourself and the people around you?

I was green when I was younger and doing this whole thing. I didn't understand what a lack of diversity was. I'm not seeing people like myself in these roles. I didn't have the knowledge or maturity to question why that was. I was like, “I have a job. I'm doing well. Why ask questions?

It takes a while. When I started out, you were fighting to be seen and heard. It is hard to even understand that, at a larger level, something is going on within this industry that is making it hard for you to be heard. I hear you. It took me a while to be like, “It's not me.” People like me are struggling to be heard, and they have to do twice the amount of work to get to the next level or get the same pace. What is advocacy? It took me a while to figure out that's a thing I need to focus on and is going to change how we work.

It's one of those things that we're conditioned to follow a formula. Go to college, do this thing, get the career, work in the career, be happy, pay the bills, and be happy and satisfied. It's ingrained in us at such a young age that that's the formula we need to follow. We forget to take a minute, look around, and say, “Is this formula allowing for an equitable society? Are we able to see how this formula may be impacting other people at different stages of their life or look a little bit different?”

It was part of my whole journey of self-discovery and figuring out who I was and being a queer woman of color and not realizing how much of that I was even hiding and discovering my neurodiversity. I wasn't questioning anything because I was following this formula. It wasn't until the dam started to leak a little bit.

I was doing this thing. I was happy. I should be great. Outside of my career, things were a struggle and challenging. I couldn't quite understand why. It took a lot of years. It's only been in the last couple of years where I'm like, “We have a problem here. There aren't enough women, people of color, and queer people in tech.

There are many things where we're like, “Why are we gatekeeping such a powerful sector of our society and only leaving it to cis-White men to run and manage? There are exceptions out there, but it's challenging because we are stuck following their footsteps and paths. It's hard because as much as we try to follow that path, we don't relate to it. We can't do it. When I started to see it, for the longest time, I was the only woman on my team. Everyone else I worked with was men. I was hiring people. Why aren't we getting more applications from women? Are we getting applications from women? We're looking at them through a different lens. What's going on here?

We did finally hire someone who's a woman. She was incredibly smart. I'm still in contact with her. I hope she looks at me as a mentor. I feel like a mentor. A lot of it is telling our stories and letting people know there's a different path to take and formula. You don't have to follow this. There are multiple ways to get that answer.

That is a little bit of the challenge with diversity and inclusion and making it actionable. It's seen as a checkbox or something where it's like, “We changed our profile picture to be a rainbow for pride month.” It's like, “That's awesome. What are you doing?” They're like, “We're doing these things. We have DEI.” I'm like, “What does that mean? Are you taking more time and doing more work to go outside of the traditional pool that you go in? Are you taking chances on people who might not have every qualification you're looking for but can do the job? Are you helping them succeed? Are you working with people to ask the right interview questions that aren't trying to trick them?”

Are you working on the culture within the company? Women who've been in the industry. When you mentioned, “The dam is starting to leak.” I have been there where I've been like, “This is it. I can't keep doing this.” By this, I mean to keep going to this corporate culture, this boys club, and keep showing up there and trying to advocate for myself. It takes a lot of energy. As companies are doing DEI work, are you doing the work within the company?

Once you get to a certain level, it gets exhausting to fight constantly. Are you changing the environment within your company to make sure those voices have the space to exist? We talked about it before during our call. When you get to that C-Suite and VP level, there are less people like us because the roadmap is for White cis men. You get jaded, and the environment keeps putting the same obstacles in your way. There isn't a roadmap.

There's this feeling of, “Don't rock the boat. I should be grateful that I'm even here and doing this.” It's BS. It's another way of social engineering to convince people that their voices aren't important. You have a job. You're doing it because you are here. You took a step. I'm not saying that's not good, but if people are afraid to challenge, ask a question, or say, “Why are we doing things this way? Is there a better approach? Here's an idea I had.” You don't give people the freedom to speak up or the safety to speak up for fear.

Even though it's against the law, we all know that it's a challenge. We've seen it with sexual harassment cases. It ends up being the person who goes, tries to do the right thing, and reports it or says something is the one who's blacklisted. It's a problem that I don't think that we're taking it seriously enough. I wish I had a better answer or knew how to solve the problem. Part of it is me working as hard as I can to get into those positions and advocate and use my position in a company or the level that I'm at for me to push back and say, “We got to stop doing this. Why are we doing this? This isn't cool.”

Take on that challenge because why am I there? If I worked hard to get there, and I've gone through all these things, and the goal is not to make it so that everyone else has to struggle to get to where I did and follow that path of like, “In order to be here, you have to struggle.” No, let's not do that. We don't need to do that. I mentioned to you this before. It was like, “Life is not pie. Society is not pie. Jobs are not pie.”

There's plenty to go around. We are stuck in this idea of perfection overgrowth. It's hard, but making those steps in and asking those questions and pushing back, there's always a respectful way to do it. Having the courage to do it, and having more of these conversations and interacting with more people, especially women in technology, other women of color, or the underrepresented communities, the more you have conversations and say, “It's okay. I'm here for you. I support you. We can do this together. Here are some strategies. Let me help you phrase how to say this.” We need to build that community together and be there to support people because going at it alone is scary. It feels like we're all alone when we're doing this.

I'm going to go back to the questions because you said some things that were profound, and I do want to dig deeper into, “It's not a pie.” Before we do that, do you want to share a story or a moment where you did something that was off script or you pushed back against the norm, and what that looked like? We're not going to solve everything, but we can do tiny little steps every time we have the opportunity. I want people to know about that opportunity given to you and how you did your tiny step, massive step.

This was back in 2017 and 2018. I had been promoted to global director of technology. The industry is always going through ups and downs, especially advertising and media. There are always ups and downs in that space. I was trying to prove myself doing a thing. I was like, “My boss left. I'm now in charge. How am I going to do this? Am I qualified to take care of my team and show leadership?”

One of the first conversations I had was when my boss pulled me into her office and was like, “We're not getting as many clients as we thought we would. We are going to have to lay people off. By the end of the week, let me know X amount of people on your team that we need to lay off.” This was terrifying. This was my first experience having one of these conversations.

I hold people's lives and careers in my hands at this point. It's sobering to have those conversations and nobody to know. Fortunately, I was already doing a lot of budget work and getting things organized. I thought about this before I left her office. I was terrified of saying this and bringing it up. I walked through the discomfort. I was like, I'm going to get fired.”

I said, “What's the number that you need? What's the total number that would help to save their jobs and at least get us to the next point while we can work through this and maybe save some money?” She was like, “It doesn't work that way.” I was like, “What about me? What about my job? I'll find something else because I make X amount. Will that help offset some of these numbers?” She was like, “It doesn't work that way.” I was like, “Why not?” These people on my team play a critical role in what we're doing. If we are going to be going through layoffs, there's going to be a lot of the work that they do that they're going to have to go through to execute this and get this done.

She said, okay, “Tell me what your thought is about the budget.” She gave me a number. It was a big number. I was concerned about the number. She said, “If we can't get there, I need to know. By this date, you need to tell me.” I was like, “Let me come back to you.” I went back to my desk and worked nonstop for the next week to get all of the budget numbers together, to put together a dashboard to talk to different people and stakeholders, and say, “Is this necessary? Do we need this? Can we reduce the license count? Are there ways that we can consolidate things?”

I put together a database with dashboards where we click stuff. It was able to visualize how much we were spending on unnecessary things and how much we could save by reducing those costs. In turn, it saves people's jobs. We did it. There ended up being another round later, which, unfortunately, I wasn't able to help with, but I was able to save my entire team's job for a longer period of time and extend it. That was me.

If you asked me, I couldn't have told you what inspired me to do that. What gave me the courage to say it? These are people. They do a good job. They've been here forever. They have families. It's bigger than them being a resource and number. It is part of my job to not only make sure that the technology stuff is running, but I am a people leader.

I'm responsible for this entire department, managing and growing these people and their careers. They're trusting me. If I can't take that step to be courageous and challenge something, you know, to advocate for them or save people's jobs, I don't have any business being a people leader. That might not go over well with other people, but it matters. I don't think we have enough of that.

You weren't off-script, Nichele. How dare you?

I was able to get away with it because people were caught off guard by me asking the question and being like, “I'm going to go off script here. I'm going to do this anyway.” They were like, No, you can't.” They didn't have time to gather. They didn't have an answer to me choosing a different path.

We need different types of brains and thinking about problems. This isn't our dig at whatever's happening in tech with all the layoffs and saying, “Managers need to do better.” We all know that executives can be paid a little less. I digress. That's my passion. I passionately hate how much executives make at tech companies, but I would like to stay employed.

Questioning the status quo and being like, “I hear you. Things are done this way, but what if we try a different way of doing things?” It's allowing those voices to exist. Not even being heard and letting them do their thing, but allowing them to exist for long enough for them to be in those positions where they can do things differently.

I was listening to a podcast where this woman, an immigrant, started a company, and the podcast was asking, “How much do you make?” She, as a CEO, was making less than what tech-starting engineers naked in New York. They were like, “How did you come up with this number?” She was like, “Given my mortgage and paying for bills, this is what I need.” It's amazing.

That's the way she approached it because she's a woman of color thinking differently. She is coming from a whole different mindset. She was like, “I love doing this. This is what I need to pay for my life. That's all I'm going to make.” It's not how we're wired to think. Going off script is what we, divergent women of color, queer folks, we're wired to think differently, to find a space for ourselves. Sometimes, it comes from a place of fear because we have to find a way to get out of a situation.

We see it in technology all the time. Let's use different technologies to solve new problems. Let's maybe try this new technology that hasn't been tested yet to solve this problem. Let's plug and play. We can do it for machines, technology, code, or different ways of managing that. When it comes to people, we can't seem to get over the concept of it's pie, and you're a person. You're going to take my piece.

How many different coding languages are out there? How many things are happening? API changed what we're able to do. That was a different way of thinking. We have AI. That's taking over. We're open to new, innovative, and diverse ways of solving challenges with technology, except when it comes to humans.

We are open to new, innovative, and diverse ways of solving challenges with technology, except when it comes to humans.

I love the way you put it, but can you talk more about, “It's not a pie?” I love how you say and describe that, but I want to hear more about it. I want people to understand what you mean when you say life and career are not a pie.

One of the things that we can reference for that is, like you were saying, CEO, C-Suite, and executive pay. It's part of that mentality of, “In order to be in the elite, I have to do X, Y, and Z.” There's only a finite amount of positions, things, availability, or space for people to exist there. If this person has it, you can't have it because there's only a finite amount. I can't believe that. I don't believe that there's only a limited amount of space that not everyone can grow.

The crazy thing about it is that not everyone wants to be a people manager, director, or be in the C-Suite. By that, there's still plenty of opportunity. It's hard because there's a fear that I'm in this good spot, things aren't stable, and if this happens, what happens to me? We've taken a fearful approach to that. I need to get mine and take care of mine before I even consider you, what you need, and how to do that. It's the saying, like, “If it isn’t broke, don't fix it.” It's broken. It's not working. We keep trying the same thing, and we keep trying to say, “Maybe we need to make our board bigger, change these positions, or do this thing.”

It frustrates me so much that if I have this thing, you can't have it either because if you have it too, it devalues mine, what I have, or what I've done. It makes me sad that we live in a society in a world. I'm hopeful. This has made me feel that way. Other people I've met have made me feel that it's not the majority that feels that way. The minority are the people who are controlling the conversations, controlling the narrative, and convincing the majority that there are a finite amount of spots. It's not true.

If we can do everything that we do as technology, we don't need another language on how to program something. Let's do it. We're all going to become experts in this thing. It doesn't make sense that we're willing to be like, “Let's have five ways to solve this one problem. We're going to pick and choose. Every place you go to, we use this instead of this. You need to learn this.” It's like, “If I know how to do this thing, I can learn how to use this other thing.” There's no such thing as oversaturation.

There's plenty to go around. I feel like I can keep going, but I want to jump into the rapid fireside of things. Are you ready? Can you share a story of a successful project or accomplishment you are particularly proud of?

I'm trying to think of the best example of one. I'm a big sucker, and I love cross-functional projects. Honestly, it makes me a little bit strange in that. Being in IT, there's a lot of stigma there about like, “IT sucks.” People are right. IT does suck. We need better IT people. It's not this thing where we put things and tools in place at the service of the people who are using those tools and businesses.

Our goal as IT professionals is to crowdsource and be like, “What problem are we trying to solve? Why is this a problem? What challenges is this posing for you? Let's go back to the drawing board and let's figure out how to solve this challenge together to make it easier. We're going to take on a lot of the work. We're going to come to you with solutions versus more problems, but I need your feedback. You're going to be using this.

I’m against people putting things in place to put something in place and say, “You have to use this.” I feel like a lot of people think IT is limiting and dictatorial in the way they operate. I hate that. One of the projects I've done was fun. I love doing workflow and process improvement projects for anything. At my previous company, they did a bunch of media and content. It was quick turnarounds, not long form. There wasn't a lot of time between full shooting to post and getting it launched.

There was a lot of manual work there when I started. It was like, “We're going to film this. We're going to manually upload this. We have to wait for that. We have to keep transferring these files over different things. The editor's going to work on it. We have to transfer it. It’s painful to watch it. It was taking people so much time and effort. We were able to sit down.

It did take about a year to get to a solid place. We put in a full production workflow environment with asset management and cloud operation for storage. This is post-COVID, but the world is still weird. People are working from home. We don't know if we're going to go back. We still need to have this massive amount of data and be accessible wherever people are right, for them to be able to edit and work on it, and not have to be burdened by like, “I have to now VPN to this machine that's at the office that might be 3,000 miles away.”

We made it easier for editors to work remotely and put in this powerful thing where it was a quick turnaround. We now have a portal where we can search for our content and media. It was a fun, awesome project. We got to a place where things that used to take people two weeks only took them a couple of days.

There are tons of projects like that. I'm a big fan of dissecting, like, “What's the problem? How can we solve this?” I don't think you might have the same problems, but solving it for different places and companies is always going to be unique. It's one of my least favorite questions. When I'm going to interviews or people are talking, I'm like, “What have you done for this? How did you solve this?” Here was the situation. Here's how I solved it there. At this place in your company, things are probably going to be different. I can approach how to solve it. It's not plug-and-play. If it were, I wouldn't have a job.

Write a script for it, and it's done.

There are things you can do like that, but it's situational. A lot of people don't realize that I can write a script and automate this thing, but if it doesn't work for how you work it, that script's going to be useless to you.

What advice would you give other women or other women of color, queer women, and neurodivergent women who are trying to find their footing in this industry?

There are a few things, and this is a challenging one. One of the biggest ones is to find your community. Find the people who are going to lift you up, support, encourage, and help you. These are the people you can bounce ideas off of and whip all that aren't intimidated by your intelligence or success. One of the most important things is finding that. It might take a while to find but don't stop searching. Those people are out there. Trust yourself and believe that what you're thinking and feeling is the right thing.

Find your community and the people who will support, encourage, help, and lift you up. Be with those who are not intimidated by your intelligence or success.

Don't believe other people when they doubt you, question you, or try to put you down because of things. That's their s***. They have their own stuff going on. Most of the time, it's not about you. If you truly believe that something's the right thing to do, it's the right approach, or you want to try solving the problem, do it. Go for it. Don't blow your budget within reason, but test it out and be like, “This works. Here you go. I saw this.”

You might have spent some extra time, but trust yourself and your instincts because they're usually not wrong. I hate to see when people have a thought or idea, and they constantly keep getting shut down. It dulls their shine and sparkle. It's hard. Don't get me wrong. I've been a victim of this, and there's been challenges that I've had to pull myself up. That's where it comes back to your community. Finding that community is the most important. Number two is to believe and trust yourself.

This is a great spot for us to leave the conversation. Go off script, folks. Trust yourself and find your people. Thank you, Nichele. Thank you for sharing your story, journey, and how you got to where you are and being candid about it. Thank you so much. I appreciate it.

Thank you for putting this together. I'm available here for you and anybody else. If they have questions, I'm happy to chat. It's not pie. I'm happy to share.

Do you want to share how people can find you?

You can find me on LinkedIn. Nichele Dudley is my profile. I'm unfortunately not active on social media. You can follow my Instagram, but I don't post anything related to work or technology there. LinkedIn is the best way to get in contact with me and reach out.

Thank you so much.

Thank you so much. I had a great time.

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About Nichele Dudley

Never one to walk away from a challenge, Nichele Dudley is a natural-born innovator. With an insatiable sense of curiosity and imagination, the IT executive and consultant is a strong believer in taking risks, and has the inner calm and grace required to see them through. Whether Nichele’s helping companies expand markets, streamline operations to boost profit, or drive exponential growth, she unites technology and business strategy to meet ambitious goals. Nichele has spent over a decade leading IT innovation at companies such as 72andSunny, Instride, and 100 Thieves always with the goal to inspire and unleash the potential of technology to drive business performance and profitability.

What brings her the most pride, however, is being able to make a difference in the lives of her team members through mentorship, advocacy and empowerment. Today, Nichele brings that same fierce dedication and steadfast commitment to all of her clients and personal projects. A dynamic communicator, Nichele has participated in numerous panels and loves that she can use her platform to educate, demystify societal norms around success, tech, and what leaning into one’s passion and purpose can look like. Based in San Diego with her partner and rescue dog, Nichele loves golf, is a big foodie, and loves spending Sundays watching football. Identifying as queer and having been diagnosed as neurodiverse in adulthood, Nichele is a fierce advocate for unique voices being heard in every aspect of life.