An Interview With Pirie Jones Grossman
Leadership, to me, involves creating an inspiring vision and then laying out the roadmap to achieve it. I also focus on working across leadership to ensure we’re doing the right thing in the right way, keeping empathy for people at the forefront, to get where we need to go. Beyond getting results, it’s about making sure that we’re aligning with the values that drive those results.
In today’s dynamic world, the concept of leadership is continuously evolving. While traditional leadership models have often been male-dominated, there is a growing recognition of the unique strengths and perspectives that women bring to these roles. This series aims to explore how women can become more effective leaders by authentically embracing their femininity and innate strengths, rather than conforming to traditional male leadership styles. In this series, we are talking to successful women leaders, coaches, authors, and experts who can provide insights and personal stories on how embracing their inherent feminine qualities has enhanced their leadership abilities. As part of this series, we had the pleasure of interviewing Kellie Romack, Chief Digital Information Officer at ServiceNow.
Kellie Romack is Chief Digital Information Officer at ServiceNow. As CDIO, Kellie is focused on driving enterprise-wide digital transformation to accelerate growth, create scale, and deliver amazing experiences built on the Now Platform and powered by AI.
As Customer Zero, Kellie and her Digital Technology team are helping shape the ServiceNow Platform direction — as both a product incubator and revenue generator — and serving as the blueprint for how organizations of every size, in every industry, can digitally transform and put AI to work for people.
Prior to becoming CDIO, Kellie was ServiceNow’s Senior Vice President of Digital Technology Experiences, leading the team charged with creating frictionless employee and customer experiences across the company. Before joining ServiceNow in 2022, Kellie served as Senior Vice President for Associate & Retail Product Experience for Walmart, supporting 2.1 million associates and millions of customers. She also spent over 20 years working at Hilton, where she led technology and business transformation, and developed agile digital commercial products and global delivery teams.
Thank you so much for joining us in this interview series. Before we dive into our discussion about authentic, feminine leadership, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
My career path was shaped by my excitement about the early 2000s dot-com boom. I was naturally curious, and the web felt like this incredible new opportunity to learn, connect, and create things that could be seen and used by people, including my own friends and family. Early on, I worked on consumer-facing web products, which was so rewarding because I could show people what I built and say, “Look, this makes your life easier!”
At Hilton, that led us to online bookings, which felt revolutionary at the time. Instead of phone calls with no visualization, you could search for a hotel on a map, look at photos, and book a trip in just a few clicks in a way that was visual, functional, and intuitive. That’s where my journey began: creating tools that solved real problems for people. Over time, my focus shifted from functionality only to creating functional, memorable experiences.
At this time, I became fascinated with the guest arrival experience. It wasn’t just about getting someone from check-in to their room — it was also about eliminating confusion, smoothing out the process, and making people feel cared for. Like our guests, I also traveled to and stayed at our various properties (and still do!). It allowed me to better understand guests’ challenges and how my work could improve their experience and deepened my appreciation for the power of thoughtful design and technology.
Another pivotal moment for me was the beginning of the iPhone era. As much as I loved my Blackberry, the iPhone launch was a lightbulb realization that even the most tactical, everyday tools could be elevated into something so seamless and human centered. That mindset stayed with me as I transitioned into leadership roles. I went from being a tactical product leader to someone passionate about crafting elevated experiences for real people. It’s been a journey of continuous learning, curiosity, and improvement.
Before joining ServiceNow, I also oversaw associate and retail product experience at Walmart, leading the team that launched the ‘Me at Walmart’ app, which gave associates the power to manage personal and work needs all at their fingertips. My inspiration has always been technology in the service of people — yes, it’s the experience and how people feel, but part of the reason they feel good is that they get value out of it. It’s led me to create unique and impactful digital experiences for some of the world’s largest brands.
Can you share the most interesting story that happened to you since you started your career?
One of the most impactful and life-changing experiences of my career happened during the COVID pandemic. At the time, I was leading digital experiences for Hilton, which had global operations spanning more than 100 countries. When the world came to a standstill, we had to make some incredibly tough decisions, including furloughing employees, taking budget cuts across the board, and shrinking our corporate office. It was one of the hardest things I’ve ever had to do as a leader.
What made it even more challenging was the personal side of it. I wasn’t just running tech, operations, and support, but also overseeing our care center, the front line for employees and customers. People called in, overwhelmed and looking for answers about their futures and how to make it through their day to day. These were deeply human moments, and they gave me a perspective on leadership that I hadn’t fully appreciated before.
I had to dig deep and ask myself: how do we make the best of a bad situation and do the right thing by our people? How do we think beyond the crisis and find ways to make the company stronger, more agile, and better prepared for the future? That’s when resilience and grit became part of my focus.
One moment that stands out was activating our hotels to serve as shelters for those in need, from the National Guard, to doctors and medical teams. It was all hands on deck, using technology and teamwork to respond in real time and get things activated quickly. We found innovative ways to optimize operations, streamline processes, and drive the business forward while facing immense pressure.
Looking back, those “unprecedented times” taught me so much about leading through uncertainty. It’s not just about solving immediate problems. It’s also about seeing the bigger picture, helping your team navigate challenges, and finding opportunities to evolve together. That experience shaped how I lead today, and it’s a reminder that even in the toughest situations, there’s always a way to adapt, innovate, and become stronger.
This experience taught me to be brave and bold, not perfect. Be a champion for others. Doing the right thing, even when it’s hard, is what ultimately drives progress. It doesn’t take long to say thank you or give feedback.
What do you think makes your company stand out? Can you share a story?
I joined ServiceNow to lead its digital technology experience, and it’s been an incredible journey so far on the rocket ship, as we call it! My team has launched numerous innovations to make employees’ lives easier. One of the things I’m most proud of is the creation of a cross-company experience team. It helps shape the way employees interact with technology, providing the tools and systems they need to get work done seamlessly every day.
It wasn’t just the technology that brought me here; it was also the people and culture. This company is truly customer-obsessed with a relentless drive to make the world work better, and that mindset is woven into everything we do. It really resonates with me.
It’s also a place where the values perfectly align with mine. We’re scaling and growing at an incredible rate, but what makes it so special is how we’re doing it — we win together. The culture here is all about grit, integrity, and championing our employees and customers. Those connections and shared values make all the difference. For me, culture and values are non-negotiable.
I also like to say that we drink our own champagne and eat our own cake daily. One of the most unique aspects is that we run ServiceNow on ServiceNow, meaning our own technology platform and solutions power our organization. We are our own best customer, so our employees know more, care more, and do more with our technology — and we constantly innovate.
Using our products internally allows us to provide feedback directly to our product teams, so they can continually iterate and improve experiences for our customers. We also love connecting with our customers and sharing stories about our implementation journeys, including best practices and lessons learned, so we can be a part of their blueprint for success.
We are experiencing the biggest technology revolution of our generation with AI. And it is especially thrilling to be at a company with one of the most ambitious generative AI (GenAI) roadmaps in the enterprise software industry. GenAI is changing everything we do, and we’re putting it into the hands of all our employees through hundreds of use cases (and counting). Our employees are actively using GenAI daily to get their work done, which helps us realize tangible value.
Our employees have saved thousands of hours using GenAI-powered search to get the info and resources they need, when they need them — like requesting a new laptop, double-checking leave policies, and more. We also rolled out our first AI Agent use cases for employees this year to further generate resolutions that help them solve their issues faster.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
The heart of my leadership philosophy comes down to three key traits, which have been the pillars to my success:
Resilience and grit — at times throughout my career, I’ve been the only woman leader or stakeholder in the room. I’ve faced moments where I had to reintroduce ideas (sometimes more than once) to be heard. Those moments are frustrating, but I’ve learned to stay focused on finding a way forward. I will always find a way to meet people where they are to make unified decisions.
Servant leadership — I’ve always prioritized this philosophy, which is about delivering performance for everyone, not just for yourself or your immediate team. Leadership is about serving the greater good while staying accountable and responsible instead of just giving orders. For example, I make it a point to focus on how our work impacts the bigger picture for the organization, not just the function we’re in. That mindset drives better outcomes for everyone.
Curiosity and empathy — leaders must understand how things work and what people need. You don’t need to have all the answers, but get the right people involved or do the research. Don’t walk past a problem — address it and get it resolved. It’s also important to step into someone else’s shoes and see the world from their perspective. Whether it’s understanding the challenges a team member is facing or diving into the details of an initiative, curiosity and empathy are essential for meaningful leadership.
At the end of the day, I’m an approachable leader. We’re all human, and clarity is kindness. When people understand what’s expected and how they’re supported, they can do their best work. My ultimate goal is to mentor and coach the next generation of leaders, so they can grow and succeed — that’s how I know I’ve done my job well.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.
As a CDIO, making tough decisions is a part of my job every day. It often comes down to balancing competing priorities and finding the best path forward for both people and the business.
One of the most challenging areas is talent. Hiring the right people for the company isn’t just about filling roles; it’s about finding that balance between what’s best for the individual and the organization. Those decisions can have a huge impact, and it can be a tough call if someone is a solid worker with a great attitude but not the right fit for the company. Sometimes, it means they just don’t mesh well with a certain team or manager, and we can work with them to find a new role that fits themselves and the company better.
Technology decisions are another big one. There’s always a mix of external and internal pressures, like stakeholders with differing opinions and the need to prioritize based on market needs or customer feedback. A key example is determining where to draw the line between “good enough” and “perfect” when it comes to user experience. It’s a constant balancing act of progress versus perfection, and that means sometimes I’m asked to draw that line, and other times my decisions get overridden.
When faced with these decisions, I always try to put myself in the users’ shoes. Whether it’s an employee, a customer, or a partner, I ask, “what would I want if I were in their position?” That question guides me, along with asking “why” to dig deeper into the needs behind the choices we’re making.
Ultimately, leadership in these moments is about innovating and moving forward without losing sight of the human experience. These hard choices have shaped the outcomes I’ve delivered and my growth as a leader.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal experience where embracing your unique leadership style, which might not align with traditional expectations, led to a significant positive impact in your organization or team?
Today’s technology leaders need to adopt a people-centric approach. We have to understand the challenges our customers and end-users face on a daily basis. When we can put ourselves in their shoes, we’re better positioned to design technology that actually helps solve their problems.
I like to ask myself, “What’s the magic behind how this technology makes people feel? Does it engage them and contribute to making the world better?” This mindset has had a significant impact on my work. One example that stands out is my time at Hilton, where I led web and mobile delivery teams and transformed the way customers interacted with the brand. Some of my proudest achievements include pioneering Digital Key technology, which gave guests seamless access to their rooms, and developing the Hilton Honors app, which allowed customers to manage their stays directly from their mobile devices.
As for my leadership style, I like to get together in a room (whether physically or virtually), figuring out a way forward and doing the work. I whiteboard ideas or focus on a tactical plan with others, creating an environment of focus and accountability that lets the team step outside their day-to-day and think bigger. I’ve found that teams often need to get out of their own heads and come from a place of yes instead of no. We get better outcomes when we imagine what’s possible and work back from there.
In fact, this people-first, solution-focused approach has allowed me to build strong, impactful teams and drive measurable results with tangible value.
In your journey as a leader, how have you balanced demonstrating resilience, often seen as a masculine trait, with showing vulnerability, which is equally powerful, but typically feminine? Can you give an example where this balance created a meaningful difference?
I don’t agree with the idea that resilience is inherently a masculine trait — it’s a human trait. In fact, when I look at the lives of women, I see incredible examples of resilience as women adapt and persevere through constant changes and challenges. In many ways, we are the very definition of resilience when it comes to navigating the unique challenges we face at every stage of our lives.
On the flip side, vulnerability doesn’t need to be labeled as feminine. To me, vulnerability means a lot of things: it’s about having the courage to trust people in an inner circle and be honest about challenges. It’s a strength we all benefit from as leaders.
At the end of the day, resilience and vulnerability are both part of being human. And together, those qualities translate into self-awareness, which allows us to examine ourselves more deeply and show up authentically for ourselves and the people around us.
As a woman in leadership, how have you navigated and challenged gender stereotypes, especially in situations where traditional male-dominated approaches are the norm? What strategies have you employed to remain authentic to your style?
It comes down to staying true to who you are. For me, confidence, preparation, and situational awareness have been foundational. I’ve often been the only woman in boardrooms or meetings full of men, and I don’t let that hold me back. I show up, participate, and make sure my voice is heard. A big part of that is being well-prepared. I stay informed, well-read, and aware of others’ interests, which helps me connect and build credibility while staying authentic to myself. It’s about finding that balance: being relatable and also showing up strong.
I’ve also learned that the most important part of having a voice is using it, and I make it a priority to advocate for equity and inclusion. If I hear a gender-biased or other inappropriate conversation, I call it out in a clear, direct way. Being bold enough to say “that’s unacceptable” is part of leading and creating a safer space for better, more inclusive conversations.
I’ve talked to so many women who are afraid of speaking up or handling someone’s negative reaction to what they say. It’s important to not let fear dictate our choices. As women leaders, we should show up authentically, be confident, and transform our seat at the table into a space or springboard for more voices to be heard.
How do you utilize emotional intelligence and active listening to create an inclusive environment in your team or organization? Could you share a specific instance where these qualities particularly enhanced team dynamics or performance?”
As CDIO, my role is to simplify complex tech issues to solve business problems while ensuring everyone feels included in the conversation. I engage with every part of our business to gain vital insights through listening and first-hand observations. For example, I partner closely across our executive team to understand their processes — everything from budgeting, planning, and employee and customer enablement to talent acquisition, skills development, and more. By staying close, I can truly understand what business problems they’re facing and how we can enable them with tech to solve those problems.
Throughout my career, I’ve jumped at the chance to work in other departments and take on new roles. Getting that well-rounded view of what needs to change unlocks true innovation. For example, during my time at Walmart leading associate and retail product experience, I joined the service desk for several hours a few times a week. I had conversations with customers and associates about what they liked or disliked about their experiences. I was able to take these learnings back to my team to inspire and shape products. One of the biggest improvements to come out of this was reinventing the returns process. We took a 60-year-old, labor-intensive system and transformed it into a seamless, “return anything, anytime, anyway” approach, making it easier for customers and associates.
What role has mentorship played in developing your authentic leadership style, and how do you communicate authentically to inspire and empower both your mentors and mentees?
Mentorship has been critical to shaping my authentic leadership style, and I approach it with a mindset of clarity, support, and growth. I always say that clear is kind. Communicating clear goals and expectations upfront makes that growth process even stronger. For any mentorship relationship to work, there needs to be psychological safety, so the mentor and mentee feel comfortable sharing openly with each other.
For mentees, I focus on helping them think through problems instead of immediately jumping in to solve them. That starts with understanding roles, responsibilities, and how I can help when needed without infringing on their autonomy. Sometimes that means sharing what I know or helping them activate, and other times it’s recognizing when to connect them with someone more specialized. The goal is always to help mentees grow and succeed. And since mentorship is a bi-directional relationship, I’ve learned just as much from my mentees as I’ve taught them.
When it comes to inspiring and empowering others, authenticity starts with modeling the behavior I’m advocating. As a leader in technology, I feel a strong responsibility to elevate the achievements of women in our industry. We’ve come a long way in getting women into leadership roles, but there’s still plenty of work to do.
For example, I’m committed to promoting inclusion through better hiring practices. I require diverse slates of candidates in my organization, and I hold my hiring managers accountable. I’m not afraid to push back and send us back to the drawing board if I don’t see that. I don’t accept excuses, because I know we can (and must) do better.
Mentorship is about showing up, listening, and creating a culture where others feel empowered and accountable to lead and succeed. That’s how we make meaningful progress.
Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”?
Each of these areas has shaped how I lead and the impact I have on my teams. Being authentic and embracing my unique leadership style has allowed me to connect, inspire, and drive meaningful results, all while staying true to myself and the values I live by.
- Building Trust Through Genuine Connections
When you lead authentically, people can sense when you genuinely care about them. I’ve found that remembering details about my team members’ lives and their personal milestones helps build trust. It’s the little things that show people you see them as more than just employees. It can be something as simple as giving a small thank you gift that you know they like or have talked about. This kind of connection fosters loyalty and collaboration. - Inspiring Others by Breaking Stereotypes
I’ve often had to challenge stereotypes by showing up with purpose and advocating for others. Whether it’s speaking up when someone is left out of a conversation or making sure diverse voices are heard, it’s important to be a strong voice for equity and inclusion. My advice to others is to celebrate and champion others’ successes — it doesn’t take much to say thank you and helps others feel seen and valued. - Driving Results with Purpose, Strategy, and Emotional Intelligence
This is the core of everything I do and what drives me every day. But it’s not just about pushing hard and getting things done; it’s about doing it in the right way, with purpose and strategy, and being focused on the right goals to add real value. That’s how we get the best outcomes and move forward together. Being a leader requires balancing emotional intelligence with strategic thinking, and I’ve learned that combining empathy with a clear sense of purpose allows me to drive results in a way that feels human and connected. That inspires people to work toward a shared goal with their hearts and minds. - Creating Vision with Strategy to Show Value
Leadership, to me, involves creating an inspiring vision and then laying out the roadmap to achieve it. I also focus on working across leadership to ensure we’re doing the right thing in the right way, keeping empathy for people at the forefront, to get where we need to go. Beyond getting results, it’s about making sure that we’re aligning with the values that drive those results. - Building Grit, Resilience, and Influence
Leading authentically as a woman often means finding creative solutions in the face of challenges. There are plenty of moments when the path isn’t clear, and resilience is key. I’ve learned that there is always a way forward, even when the road is tough. I encourage my teams to find that path and make things happen. It’s important to model that grit and perseverance while influencing positive change, even in uncertain circumstances.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
I would focus on democratizing access to high-quality education, information, and lifelong learning opportunities. Knowledge and skills are the great equalizers of our time, and when combined with the power of technology, we can unlock human potential on a global scale for the greater good. Imagine a world where anyone, anywhere, has the tools they need to grow, learn, and succeed. That’s a vision worth striving for.
Another movement close to my heart would be centered on the power of kindness. You never know what someone else might be going through, and a little compassion can go a long way. Whether it’s a simple gesture or a genuine conversation, kindness has the potential to transform others’ lives more than we realize.
Both movements — education and kindness — share a common thread: creating opportunities and making the world a better place by empowering and uplifting others.
How can our readers further follow you online?
Readers can follow me on LinkedIn here: https://www.linkedin.com/in/kellieromack/
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
Leading with Heart: Kellie Romack Of ServiceNow On The Power of Authentic Women’s Leadership was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.