Leading with Heart: Jennifer Spire of Preston Spire On The Power of Authentic Women’s Leadership

An Interview With Pirie Jones Grossman

Pirie Jones Grossman
Authority Magazine


I’m empathetic, but still hold people accountable. I do not avoid conflict, but also don’t strive to cause conflict. Instead, I listen, treat each situation uniquely and provide clear feedback and support. I’m direct and results-driven by nature, yet I have an open-door policy and I’m intentional about developing a relationship with every team member. I give my employees a sense of ownership, allowing them to lead with their own unique ideas, voice and strengths. I have always made a conscious effort to not position myself as a mother figure, but instead as a leader, teacher and supporter who is focused on empowering people, and sometimes using tough love to do so.

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 Jennifer Spire.

Jennifer Spire joined Preston Spire in December 2016 and became owner/partner and CEO in January 2019. Throughout her tenure at the agency, Jennifer has played a leading role in reshaping the values of the agency, anchored in championing the agency’s ethos, “Good Wins.” This mantra speaks to her beliefs that brands win by being positive, honorable, involved and compassionate about their customers and the world they live in.

Jennifer has been asked to speak around the country on strategy and marketing trends. As CEO she provides vision and thought leadership for the agency and its clients, and has been recognized multiple times as a top woman in business. A granddaughter of an original Mad Man, Jennifer is an expert in a wide range of industries including financial services, healthcare, lottery, consumer packaged goods, and more.

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?

Since I was a little girl, I always knew I’d lead an advertising agency. As the granddaughter of one of the original Mad Men of New York — with clients that included Lucky Strikes, Lehman Brothers and television talk show host Mike Douglas — I grew up dreaming of working at and one day running an agency of my own. I didn’t play with dollhouses like many of my friends. Instead, I played business. I remember when I was nine, sitting at a desk pretending to review copy, print layouts and make deals.

In 2021, my childhood dream came true, as Minneapolis agency Preston Kelly officially became Preston Spire and I became one of only a handful of women with my name on the front door of a Minnesota ad agency.

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

My most interesting story takes me back to the very beginning of my career, right out of college. There were no brand management or agency positions available, so I started in advertising sales at a media company selling radio and newspaper ads. I pushed the leaders of the company to allow me to represent the ad agencies so I could learn how they work.

After one year, I was offered a position to launch a new media department at a small ad agency. I was only 23. Ihad no idea how to be a media director or how to build a whole new discipline. But I used courage and initiative to fake it until I made it! I researched, learned and worked hard. I was resourceful and ambitious, and I made sure to learn all aspects of the agency business. In addition to my role as media director, I answered the phones and I organized the office supply closet (in my suit, believe it or not, because back then, we were all dressed up at the office). I was a project manager, production assistant, PR specialist and account manager. I used that same courage, initiative and work ethic to pursue my long-time dream of being an agency owner and leader.

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

Our leading mantra at Preston Spire is “Good Wins.” In an endless sea of online noise and negative chatter, our mission is to supercharge the good in brands and create innovative work that celebrates what makes brands great, so that they can positively and authentically grow.

Our employee-owned agency nurtures a culture that empowers individuals from different backgrounds to lead with bold creativity, relentless innovation, a competitive spirit, and the challenge to perform at the top of their game.

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?

Initiative is the character trait most instrumental to my success. From day one of my career, I have never sat back and waited for opportunities to come to me. I’ve always been ambitious, resourceful and creative in finding ways to seek out the right opportunities. It comes from the strong work ethic that I learned from my grandfather and my father.

Courage is another important character trait, giving me the ability to try things I’ve never done before, to go out of my comfort zone and take smart risks. Courage and initiative go hand in hand, and both were essential to my first big career move, becoming a media director in my early 20s. Without these traits, there is no way I would have said yes to that position, especially without guidance or a mentor to help lead me.

Being a maximizer — seeking to transform something strong into something superb — is another character trait that has helped me succeed in my current position as CEO and agency owner. I’m passionate about discovering people’s unique strengths, nurturing and refining them to guide them toward excellence. A focus in my role today is helping others maximize their talents to be the best they can be, because when they succeed, our clients and our agency succeed.

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?

By far the hardest decision is always around letting people go, whether it be for financial reasons, restructuring or performance. I have been told by other business owners that it is part of running any business and it should not be taken personally. But these decisions are personal, directly impacting people’s lives and their families. I do not take these decisions lightly and I have always done everything possible to prevent having to make that hard choice.

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’ve always seen myself as a leader, but I don’t align with traditional expectations.

I’m empathetic, but still hold people accountable. I do not avoid conflict, but also don’t strive to cause conflict. Instead, I listen, treat each situation uniquely and provide clear feedback and support. I’m direct and results-driven by nature, yet I have an open-door policy and I’m intentional about developing a relationship with every team member. I give my employees a sense of ownership, allowing them to lead with their own unique ideas, voice and strengths. I have always made a conscious effort to not position myself as a mother figure, but instead as a leader, teacher and supporter who is focused on empowering people, and sometimes using tough love to do so.

I hope that my leadership style makes a positive impact every day, even in small ways. But the impact of my leadership style was recently recognized when our agency won Ad Age’s “Best Places to Work” award, a massive recognition from our own employees of our agency’s authentic, supportive and collaborative team culture.

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 believe there needs to be a balance of these traits. A person, whether a woman or a man, can be both resilient and vulnerable. I am strong and can handle stress, tough times or defeat better than most. The employees at our agency have also seen me cry on some occasions when watching an emotional video we’ve created, while giving out an award to someone very deserving or after losing new business.

I want our team members to be tough and strong, but also feel safe to process their vulnerability when needed.

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?

Fortunately for us, marketing is no longer a male-dominated industry and there is no need to challenge gender stereotypes. Everyone is supported to be their authentic self, especially at our agency. Two of our core values are openness and originality, promoting support for the development of diverse ideas and approaches. We treat everyone the same, whether they are female, male or nonbinary, have children or not, are from similar or different cultures.

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’ve been told that I’m really good at reading the room. This is something our industry teaches us — we have to understand a variety of industries and be comfortable with different personalities. Because of that, active listening is ever present. I try to not let things go ignored. If I see something, I address it in the moment with empathy.

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?

I’ve been fortunate to build strong bonds with people just starting out in the industry and use my experience to help them chart their own career path. This is an industry that luckily encourages originality and authenticity, so as a leader it’s important for me to present my most authentic self, as that sets the tone for our agency’s culture.

This is from one of my mentees, “As someone that you mentor, I feel like the ‘you’ I see and witness is the same ‘you’ that you present to the entire agency. We have real, serious, direct and fun conversations and you maintain that tone with everyone. You don’t take yourself overly seriously and have a way of lightening stressful situations but in a professional way.”

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

It’s important to lead with empathy, and the potential for pitfalls are minimized as long as you hold people accountable at the same time — accountable for showing up and delivering their best work for their teammates and clients.

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?

As we’ve done for brands with Good Wins, I would start a movement focused on leading with positivity and looking for the good in people. When you do, you maximize their potential, and take them from strong to superb.

How can our readers further follow you online?

People can find more information about our agency at www.prestonspire.com, and can find out more about me and follow along on my LinkedIn.

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.