Leading with Heart: Ann Stanberry of Liberty Mutual Insurance On The Power of Authentic Women’s Leadership

An Interview With Pirie Jones Grossman

Pirie Jones Grossman
Authority Magazine


Just be yourself: I think it’s so important to stay true to yourself in everything that you do. I have been told that I bring “the energy” and I love receiving that feedback. It signifies that I’m connecting with others on a deeper level and I’m remaining authentic to myself. It’s also much more rewarding and a lot less effort than trying to be something you’re not.

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 Ann Stanberry.

Ann Stanberry is Executive Vice President and Chief Strategy Officer of Liberty Mutual Insurance, the fifth-largest global property and casualty insurer. In her role, she helps the organization understand trends and disruption, set the overall strategy, drive cross-business unit engagement, execute key strategic priorities across the enterprise, and innovate new products and services that position Liberty for future success. A crucial leader at Liberty, Ann previously served as Vice President, Strategy and Planning for the company’s Global Retail Markets business. Ann is a leader in Liberty Mutual’s LEAAP@Liberty employee resource group and was previously a leader in Liberty Mutual’s WE@Liberty employee resource group. Externally, Ann is on the boards of Visible Hands, a company that supports underrepresented founders by providing the initial capital, education and network necessary to launch their startups, and Nurtury, a Boston nonprofit that supports young children by promoting school readiness, healthy development and strong families. Ann earned her BS and MBA from Duke University.

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?

I’ve always loved the challenge of solving big, ambiguous problems and bringing people together to deliver a shared goal. As Liberty Mutual’s Chief Strategy Officer, I love that I get to work across teams and business units to set the future direction of the organization in a way that provides greater clarity, enables the distinct pieces to work better together, and creates an engaging and motivating environment around our future. My passion for this type of work really came from my upbringing and my need to ‘figure things out’ as a kid. My parents immigrated from Thailand for their education and decided to stay after I was born in hopes of providing me with greater opportunities. They worked hard to give me every opportunity they could — and I have done the same since as I never wanted to let them down. I found that growing up, I needed to embrace and try on different perspectives and understandings of the same world. It helped me see problems from multiple angles and understand the underlying connections that could be made to bring things together. I also found that I needed to embrace creativity and have a strong sense of perseverance — asking “how might we” to fully explore possibilities and continue to move things forward.

Throughout my 20+ year career, I have been able to expand my capabilities and my perspective across multiple different industries, businesses, and types of challenges. I started my career at GE Financial in their Leadership Development Program and then joined their internal audit staff. It was a unique opportunity to experience different parts of the organization in a condensed timeframe. Through my time with GE, I lived in six different cities, including London and Sydney, within a four-year timeframe and that experience really kickstarted my passion for meeting new people, building relationships, and experiencing new things.

I wanted to continue to do that on a broader scale so after business school, I joined Kearney, a management consulting firm, and traveled weekly to clients across the globe to help them solve some of their most pressing and significant strategic problems. In 2015, I joined Liberty Mutual to create their strategy organization within their US Consumer business. I led the organization through several large-scale transformations and continued my development through opportunities to build and lead teams that included Mergers & Acquisitions, Venture Capital, Innovation, Capital & Portfolio Management, and Financial Planning & Analysis. It has been a truly rewarding experience getting to understand the organization more deeply and having the opportunity to set the strategic direction, explore how trends will evolve, execute on critical priorities, experiment with new products and technologies, and see the impact you’re having on the future of the organization.

Can you share the most interesting story that happened to you since you started your career?

I don’t know if I would call it an interesting story, but one of the most important shifts I’ve had in my career has been becoming a parent. It has truly shaped how I think about my work, what is important to me, and where I find my daily motivation. Before kids, I was overly focused on my career and rarely thought about my own needs. Having kids forced me to reconsider all of that because I realized that I needed to be “at my best” to effectively care for both my family and my team. I took time understanding where I was spending my time and where I wanted or needed to spend my time. I took stock of how often I was checking emails and responding to work texts when I was with my kids. I made a concerted effort to create a better balance across the various aspects of my life. Don’t get me wrong — things are never in perfect balance — but creating boundaries, recognizing the importance of self-care, and being fully present in the moment helped me be more productive, engaged, and fulfilled across all aspects of my life and career.

What do you think makes your company stand out? Can you share a story?

Liberty Mutual does an amazing job at creating an environment where you can bring your whole self to work and thrive both personally and professionally. I don’t think I truly understood the impact this could have on teams until I joined Liberty. I remember feeling unsure about sharing so much of my own story or the small things I was dealing with in my personal life with others at work. I had always been taught to “leave it all at home” and to put on your professional façade while in the workplace. Realizing that being true to your authentic self and creating an open environment where you can connect with others on shared experiences helps build stronger trust amongst the team. A lot of this work has been elevated by the Employee Resource Groups (ERGs) we have at Liberty. I have been significantly involved with our Women at Liberty and Pan-Asian ERGs, which provide a forum for people to connect, share experiences, and build community. They also create a supportive environment that is essential to personal and professional growth. I have taken on many challenges and risks throughout my career, and I have never felt so supported by my team, my mentors, my peers, and my managers than I have at Liberty. By building a more inclusive environment, we’ve been able to bring more ideas, experiences, and expertise to the table and build better solutions to the problems we’re trying to solve– all while making it more fun, engaging, and motivating as a team.

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 three key character traits that have been most instrumental to my success are being collaborative, trustworthy, and adaptable.

  • Collaboration: I have always been more of a “we” than a “me” oriented person. I’m energized by team environments, and I love bringing people in to build on ideas and solve challenging problems together. I find that the best ideas aren’t usually a single one, but a multitude of different expertise, perspectives, and experiences that come together to debate, form, and shape the solution. I’ve found that being open to new ideas and having a collaborative approach to solutioning creates stronger results, build better relationships, and creates greater alignment amongst the team in the end.
  • Trustworthy & Reliable: I think it’s important to always act with integrity in everything that you do. It’s the foundation for building trust with others and it’s core to my personal values. Growing up, I never wanted to let anyone down so being true to my word was very important to me. In my professional life, I have found that being consistent and reliable in terms of the quality of the work you deliver as well as the support you provide your team has served me well in building a trusted reputation with leaders and peers alike.
  • Adaptable: Through my experiences early on in my career, I’ve learned to be flexible and adaptable to challenges or opportunities that come my way. I have moved between different business units, functions, cities, and even countries in a relatively short amount of time. I found that I had to get comfortable jumping in, learning quickly, making decisions, and adjusting along the way. What helped was quickly being able to prioritize what was “critical to know” and what was more “nice to know” as we were addressing problems. I think it also instilled in me an experimentation mindset that focuses on quickly testing and learning to de-risk future moves and accelerates problem solving for the team.

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.

Early on in my career, I always pushed myself to be a top performer — fastest to promotion, accelerated track to partner, etc. There was constant pressure to keep climbing up the ranks because that’s how “success” was defined. I think the hardest decision I made was to stop the race and spend some time soul searching and figuring out what I want out of my life and my career. It was challenging because I was told a hiatus would impact my promotion track, but I desperately felt the need to push the “pause” button so I didn’t lose myself in the corporate climb.

I decided to take a break from consulting for six months and used the time to explore my passions and understand what truly motivated me. I jumped into interior design projects (a personal passion of mine), created a business plan for a potential start-up, spent some quality time with my family, and reflected on what I enjoyed most throughout my career. Ultimately, I discovered that I really did love working for big companies and solving interesting, complex problems. However, I wanted to do more than advise companies — I wanted to own something end-to-end and see the impact of the decisions I made all the way through. I wanted to be able to support, lead, and develop a strong team of strategic thinkers that could make an impact in the world. I also wanted to feel like I could continue to grow and develop in my career, while having more balance in my life for my family and myself. Taking the time to recognize what was important to me was a big pivot point in my career as it resulted in making the move to Liberty Mutual. I’ve felt fortunate that I’ve been able to find a place that is both forward-looking and supporting — tackling complex challenges is a rapidly evolving market with a supportive environment where you can continuously grow and develop.

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?

I once received feedback about needing to be more direct and authoritative in my leadership style to be successful as a woman in a corporate environment. It is something that I have often struggled with throughout my career because my personal style hadn’t always aligned with the traditional leadership traits that represent what “good” looks like. I think it’s always important to listen to feedback and push yourself outside of your comfort zone — but you can’t lose who you are in the process. As I matured in my career, I realized that I wasn’t going to be successful trying to emulate something that I’m not. Rather, I needed to understand, hone, and appreciate what made me unique and successful as a leader and broaden the perspective of what “good leadership” really means. My personal leadership style is highly collaborative and reflective of my dual identity and upbringing. I’ve always valued spending time with others, listening and understanding various perspectives, working together to figure out the best way forward, and bringing people along so that they feel ownership over what’s needed to deliver. I believe that the balance of both the EQ and IQ in how I approach problem solving has helped me be successful particularly in driving cross-functional and cross-business unit efforts that require more influencing and alignment to get things done.

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?

The duality of how to act as a woman in leadership is a struggle that I’ve had to work through as I have navigated my career. We’re told to be strong — but not too aggressive — and to be empathetic, but not too emotional. What’s most important is to be true to yourself and to focus on being the best version of you — because that’s when your authentic style will shine.

Earlier in my career, I rarely showed vulnerability as I had been told that you shouldn’t come across as too emotional. I became very good at compartmentalizing and remaining unflappable when things were thrown my way. It served me well early on in my career given the environment I was in, but as I took on bigger leadership roles, I found that I needed to be more vulnerable with my team to be able to build a strong connection and create the space that would allow them to feel comfortable expressing themselves and anything they may be struggling with. I realized just how important this was when I had a team member approach me in tears, overwhelmed by stress as we were collaborating on a major three-year project, working across multiple time zones, and making difficult decisions on behalf of the company. I realized that I too had been feeling the burnout but was keeping it under tight wraps to keep everything moving. I shifted quickly and created the space to pause, check in, and have a candid conversation on how everyone was doing personally. I had to be vulnerable myself — sharing challenges I was having with juggling a young family and navigating tough decisions. It was an unlock for us as a team, as we started to build trust and openness to share and support each other so that we could successfully deliver over the long-term. For me, the combination of resiliency and vulnerability is important because it ensures you’re continually finding new ways to rise to the challenge, while also recognizing how tough things can be and the importance of supporting your team and yourself through the journey.

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?

I used to feel out of place, particularly early on in my career, as I had to navigate through a more traditional work environment and client organizations that were highly hierarchical and authoritative. I remember thinking that I needed to be more aggressive to be heard and that I should curb my natural enthusiasm to be taken seriously. However, I realized quickly that trying to be something that wasn’t true to my nature was not going to lead to long-term success. I believe that being an authentic leader is important to building the trust and relationships you need to connect, collaborate, and deliver with your teams, colleagues, partners, and clients. I think what helped me along the way was remembering these three things:

  1. There’s never just “one” way: When there is a dominant type of leadership style at the top, you begin to think that those are the only behaviors and characteristics that are needed to be successful. I found that it was critical to open my aperture of what “good” looks like and figure out the blend of characteristics that worked for me. Good leadership is not about a single specific style, it’s about being intuitive and understanding what is needed in a particular situation or with each person/team and being able to flex across a multitude of styles in order to be effective.
  2. Focus on both the “how” and the “what”: I found that what was most important to me was not only achieving the outcome the team was striving for, but also ensuring that the way I achieved the outcome helped pave the way for success in the future. The “how” you go about engaging with others is so important in creating stronger relationships, engagement, and a deeper understanding of the organization in the long-term. I believe that investing the time and seeing the value in bringing others along versus leaving a trail in your wake has helped me continue to grow and be successful throughout my career.
  3. Just be yourself: I think it’s so important to stay true to yourself in everything that you do. I have been told that I bring “the energy” and I love receiving that feedback. It signifies that I’m connecting with others on a deeper level and I’m remaining authentic to myself. It’s also much more rewarding and a lot less effort than trying to be something you’re not.

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?”

The environment I create with my team is one where we embrace our differences, welcome all perspectives, and encourage each other to feel comfortable putting all ideas on the table. As a team, we’ve created shared norms and embedded ways of working that incorporate emotional intelligence and active listening. We reserve unstructured time at the beginning of meetings to check-in with each other and understand where we are in the moment and what might be getting in our way of being present. We have gone on leadership journeys together where we share the highs and lows in our personal and professional life and how they shape who we are today.

Spending time getting to know each other personally creates a deep connection and builds trust amongst the team. We practice “stepping up” and “stepping back” in meetings to acknowledge when someone may be taking up too much space in the discussion and needs to step back to allow other perspectives to be heard. We respect the time that we have together — limiting distractions and focusing on being present, listening to each other, respecting diverse perspectives, and problem solving together. These tactics have helped improve our team dynamics and performance significantly. Our monthly pulse survey results have been on the rise — with team members indicating that they feel connected, can be themselves at work, and feel heard and trusted. As a team, we’ve been even more successful in tackling complex problems, seeing connections across the teams, and coming together as one in service of our shared goals.

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 played such a critical role in my development throughout my career. I think it’s so important to create a network of supporters, advisors, and challengers that can hold the mirror up for you and help you become the best version of yourself. I have had both formal and informal mentors that have spanned different industries, age-ranges, and genders. I have found that not every mentor relationship is the same, but with each one you are on a continuous learning journey that’s critical to your long-term success. As I’ve grown in my career, I’ve also had the opportunity to be a mentor and advocate for others navigating their own journeys. These relationships have been so fulfilling because I have learned so much from my mentees and our discussions have made me more introspective and reflective about my own journey, choices, and experiences.

In terms of authentic communication, the mentor-mentee relationship is a special one that requires trust, respect, and a deep connection. You need to be open, honest, and vulnerable with each other to fully explore challenges you are facing (or have faced), how you approached it, what you learned, and how you grew from it. You also need to be willing to listen compassionately, while still providing balanced feedback and challenge each other to see things from various perspectives. The most valuable mentor-mentee relationships to me are ones that push me outside of my comfort zone, challenge me to see things in multiple lights, and support me through a journey of self-discovery that enables me to continue to develop and grow.

Ok super. Here is the main question of our interview. Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”? If you can, please share a story or an example for each.

I believe that being leading authentically unlocks your ability to lead teams and deliver results in a way that brings people together, creates connections, and sets the foundation for continued high-performance. Overall, the five biggest areas of impact I see are:

  • Improved problem solving
  • Greater alignment and ability to execute
  • Stronger trust and deeper relationships
  • Empowered teams
  • Enriched personal growth

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

I think sometimes people can conflate empathy with being too emotional or not being able to take action. I believe that being an empathetic leader means that you are more in tune with the needs and mindsets of an individual, team, and the organization. Those qualities make you more effective in being able to understand the underlying issues, address them, and create a more holistic and realistic path forward to move teams through the change curve and deliver on desired outcomes.

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. :-)

Imagine a movement where all students had access to education and the support they needed for long-term success, and the ripple effect it would have in our communities? Early access to education has a profound long-term impact on children and it is something I’m really passionate about. As a board member of Nurtury, a nonprofit organization that supports Boston’s children most in need through school readiness and healthy development, we are creating more vibrant and abundant communities. I would love to see that same approach to education adopted across the country.

How can our readers further follow you online?

LinkedIn: https://www.linkedin.com/in/annstanberry/

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About The Interviewer: Pirie is a TedX speaker, author and a Life Empowerment Coach. She is a co-host of Own your Throne podcast, inspiring women in the 2nd chapter of their lives. With over 20 years in front of the camera, Pirie Grossman understands the power of storytelling. After success in commercials and acting. She spent 10 years reporting for E! Entertainment Television, Entertainment Tonight, also hosted ABC’s “Every Woman”. Her work off-camera capitalizes on her strength, producing, bringing people together for unique experiences. She produced a Children’s Day of Compassion during the Dalai Lama’s visit here in 2005. 10,000 children attended, sharing ideas about compassion with His Holiness. From 2006–2009, Pirie Co-chaired the Special Olympics World Winter Games, in Idaho, welcoming 3,000 athletes from over 150 countries. She founded Destiny Productions to create Wellness Festivals and is an Advisory Board member of the Sun Valley Wellness Board.In February 2017, Pirie produced, “Love is Louder”, a Brain Health Summit, bringing in Kevin Hines, noted suicide survivor to Sun Valley who spoke to school kids about suicide. Sun Valley is in the top 5% highest suicide rate per capita in the Northwest, prompting a community initiative with St. Luke’s and other stake holders, to begin healing. She lives in Sun Valley with her two children, serves on the Board of Community School. She has her Master’s degree in Spiritual Psychology from the University of Santa Monica and is an Executive Life Empowerment Coach, where she helps people meet their dreams and goals! The difference between a dream and a goal is that a goal is a dream with a date on it!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.