Leading with Heart: Mary Cannon of CityPickle On The Power of Authentic Women’s Leadership

An Interview With Pirie Jones Grossman

Don’t forget the fun! Facilitated team bonding goes a long way in creating a cohesive business culture. Carve out time during a strategic planning session for a get-to-know-you game. Perhaps each team member shares an unexpected fact about their life.

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 Mary Cannon.

Mary Cannon is the Co-founder and Co-CEO of CityPickle, the leading urban pickleball brand. In August 2021, Mary and her long-time friend Erica Desai founded CityPickle. Mary and Erica met 15 years ago when their children attended the same preschool in New York City. CityPickle debuted NYC’s first indoor pickleball club, featuring climate controlled courts and a full bar and restaurant, making it the ideal destination to connect in person, spend quality time and host events. CityPickle operates 14 courts in Central Park’s Wollman Rink during the spring, summer and early fall. The brand brings the joy and community of pickleball to thousands through its seasonal activations; locations include Hudson Yards, Union Square, Brooklyn’s Industry City and Philadelphia’s Dilworth Park at City Hall.

Mary began her professional career in Real Estate Investment Banking at Goldman Sachs, and her business experience includes roles with Starwood Hotels and investment firm Charlesbank Capital Partners. For the past two decades, Mary has served as a nonprofit leader. As Board President for Room to Grow, Mary furthered the nonprofit’s mission of supporting families living in poverty. Mary also served as Board Vice President and Treasurer for Sanctuary for Families, NYC’s leading service provider for victims of domestic violence. Mary received her MBA from Harvard Business School and her AB from Harvard College. She lives in New York City with her husband and three teenagers.

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

“Re-emerging” into the business world with the founding of CityPickle.

Post college, I was on a fast-track finance path, beginning my career in investment banking at Goldman Sachs. After returning to Harvard for business school, I joined a private equity firm where I focused on real estate investments. I eventually took a 14-year hiatus from the business world to focus on my family and raising my three children. During this time, I continued to grow as a professional but in the non-profit sector. I dedicated myself to causes that I deemed important, like childhood poverty. I eventually graduated from uber-volunteer to Board leader. I have enjoyed my different chapters and each has led me to where I am today, an entrepreneur in the fast growing pickleball industry. Lessons learned and skills honed in each chapter have made me a more effective business leader today.

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

CityPickle has a compelling need to spread happiness in the world — through pickleball. Exacerbated by Covid, our country, mired in digital interactions, is facing an epidemic of loneliness. We are not connecting in real time and space. A solution to this? Pickleball. Seriously. Pickleball is easy to learn, appeals to both serious and first-time athletes, and is perfect for all ages. Even the U.S. Surgeon General, Dr. Vivek speaks to pickleball’s power to bring communities together and points to our very welcoming sport as an important antidote to the far-reaching negative health effects of loneliness. CityPickle to the rescue! Our team takes this mandate — spreading connection and thus, happiness — seriously. CityPickle provides the infrastructure to promote community. Never played pickleball? Join our group Introductory Clinic. Experienced player? We have the perfect league for you. We love watching friendships begin on the court and extend well beyond. We even hosted an engagement proposal on a CityPickle court!

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?

Creativity, diligence and optimism.

Creativity — As first-time entrepreneurs, Erica and I formulated a brand from scratch and started the first pickleball club in NYC. Every aspect of this journey requires creativity, from devising pithy marketing slogans to structuring corporate partnerships.

Diligence — We started CityPickle in August 2021; I think I have worked every day since except for a few. I don’t work Christmas! I love building this company so it is with joy and exhilaration that I work. Starting a new venture demands immense attention to detail. Newsletter typos can hurt a fledgling brand. Every line of voluminous real estate leases must be read. This all takes time and diligence. There are no short-cuts. Creativity fuels vision, but inspired vision goes nowhere without a tireless work ethic.

Optimism — You will never meet a more optimistic person than I am. I have never once wavered relative to CityPickle’s tremendous value proposition, but my optimism derives from my confidence that our team will always work through the challenge at hand. And there are always challenges! One of our company mantras is “We will figure it out,” and we do. This attitude has served me well in life; believing every problem has a solution means nothing is too daunting.

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.

Parting ways with an employee, particularly a talented person, is difficult. That conversation is always hard, and human nature wants to avoid it. Avoidance comes with a price tag though. Culture fit is critical for an organization’s success. As a leader you need a team with diverse skills and styles but that remains cohesive and aligned. Sometimes a true fit cannot be assessed until on the job. Once it is clear that there is misalignment, better to remedy it quickly.

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?

We all have unique leadership styles, although I do not think of mine as being particularly untraditional. I am a confident leader, having accumulated enough life experience to assert my opinions and move forward quickly which is critical for a start-up. The balance I strive to achieve is also being quick to say, “I don’t know” when true. I hope this speaks to my authenticity as a leader. This allows room for a more experienced or better-versed colleague to step up and exert leadership. A successful leader knows when to defer to others.

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 respectfully disagree with these gender stereotypes. The most resilient people I know are women. Find a more resilient person than a working mother! Over decades of leadership in various roles — mother, coach, board president, CEO, I have come to learn that a successful leader does not have all the answers, nor should she. A skilled leader knows the right questions to ask and then builds a capable team to pursue the answers together. Facilitating a spirit of collaboration, a trait not limited to men or women, is a critical one to ensure long-term success.

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 have been blessed to always have strong female leaders as mentors. From elementary school through high school, every head of my school was a woman. I was an accomplished athlete, playing two Division I sports in college. Every high school and college coach I had was a woman. (My mom was my first ever coach.) I admire the women who lead the nonprofits to which I dedicate my time. I was raised to be a leader and to experience first-hand that women are outstanding leaders. Yes, there are certainly too few women leaders in finance and certain other industries. Lucky for us all, leadership skills are not confined to a trading floor. I try to model the productive leadership skills I admire in others — both men and women. Being a female entrepreneur in the rapidly expanding pickleball industry, America’s fastest growing sport, can also have its benefits. Many find CityPickle’s origin story unique and compelling which has drawn positive attention to our brand.

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?”

I am purposeful in ensuring all voices are heard, literally. I will devise meeting agendas that necessitate all members of the team participate. For example, we start our weekly Monday team meetings with an inspiring quote. We rotate weekly who chooses and shares the quote. This facilitates every voice being heard but also enables every team member, whether C-suite executive or recent college grad, to share their vision for CityPickle that week.

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?

As I detailed above, the power of inspiring mentors is profound. I emulate the mentors, mostly women, in my life daily. I am mindful about professional development and regularly seek growth opportunities for my team. Sometimes this means extending a meeting invite to a junior colleague whose presence is not necessary, but whose attendance will be educational.

Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”?

1 . Communicate directly and clearly, even in challenging situations. This honesty will help establish productive communication throughout the company.

2 . A diverse team is a strong team. Hire employees who complement leadership, not mimic current leadership. Although tempting, the candidate who reminds you of you probably won’t bring as much value to the company. You are seeking a broad array of experience and skill sets to build the most effective company possible.

3 . Ensure your team feels appreciated. Publicly note the small victories: a particularly detailed-oriented report, an attempt to learn a new software, courage to offer a contradictory opinion during a meeting. It matters and will instill confidence in your team leading to further successes. Say thank you early and often.

4 . As a start-up moving quickly, we cannot fear failures. Rather, we speak frequently about the importance of learning quickly from our mistakes. As a leader, you construct the paradigm for your company. Make it a positive, productive one, and your team will rise to the occasion.

5 . Don’t forget the fun! Facilitated team bonding goes a long way in creating a cohesive business culture. Carve out time during a strategic planning session for a get-to-know-you game. Perhaps each team member shares an unexpected fact about their life.

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

No. An empathetic leader, whether a woman or a man, is a powerful leader.

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. :-)

Let’s end the epidemic of loneliness in our country and increase our nation’s health, both physically and emotionally. The answer: pickleball! Put a paddle in every American’s hand. Local governments should convert under-utilized space to pickleball courts. Connecticut Senator Chris Murphy advocates using a portion of health care dollars on building social connection, including pickleball programming, since it ultimately saves our country from the immense financial burden from illnesses like early-onset dementia. That gets my vote!

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!