A boss of mine once gave me a very value piece of advice. It was at a time in my career when I was feeling a bit “stuck.” I had been feeling stagnant as a result of being in the same role and level for a few years. I was frustrated that neither my boss or other leaders were helping my career along. During a career discussion with him, I shared my feelings of frustration. He was surprised by what I had shared and said, “Bridget, you should realize that I am not a ‘mind-reader’ nor is anyone else that I know.” His advice to me, which I took to heart then and put into action ever since, was to “just tell people what you want.” What I have come to learn is that the best way to get to where you want to go is to know what you want and then share it with others.
As a part of our series about strong women leaders, I had the pleasure of interviewing Bridget Perry, CMO at Contentful.
Bridget spent the past 20 years leading marketing at established and early-stage technology companies. Bridget led Adobe’s commercial marketing through its transition to SaaS and launch of a digital experience platform. Most recently, Bridget led Adobe’s marketing across EMEA. Bridget also held leadership roles at Microsoft across enterprise marketing, partnerships and sales. Bridget got her start in technology at a digital agency, incubating early-stage ventures and helping established brands adopt digital. Bridget holds a BA from Boston College and an MBA from Yale School of Management. Outside of work, Bridget loves spending time with her family and outdoors — running, skiing, hiking, biking and paddling.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I was a history major in college and spent the first 6 years of my career working in the non-profit sector. I worked for an organization that served refugees and immigrants who had come to the US as a result of conflict. So, you could say that I had a very unconventional start to my career and an unusual path to where I am today. I took away a number of valuable lessons from this early part of my career which I continue to draw from today. I learned how to work with diverse communities and cultures to understand their challenges and needs and from this, design, build and launch new programs that had a real impact on people’s lives. I also learned how to raise funds, manage people, lead organizations and to operate programs and services on a shoestring budget.
I discovered my passion for building new things and leading people and organizations. I decided to expand my management and leadership skills by going back to school and received an MBA at the Yale School of Management. I graduated at the time when internet technologies were emerging and reshaping the business landscape. The potential for this technology to reshape the world, business and our everyday lives was both intriguing and exciting to me. My first job out of business school was as a strategy consultant at a high-growth digital agency. I’ve worked in technology ever since.
Can you share the most interesting story that happened to you since you began leading your company?
I was introduced to Contentful at the end of 2019 and within a couple of months had accepted an offer to become CMO. Within a few weeks time, COVID had become widespread and Contentful, like many other businesses, closed all physical offices and shifted to 100% remote work. In addition, between the time I decided to join Contentful and my start date, the global economic environment had dramatically changed. I had accepted an offer at a high-growth, early-stage company doubling in revenue every year and within a matter of only a few weeks found myself starting in the midst of a global economic recession.
The first meeting I joined focused on replanning which was based on a few assumptions and a lot of unknowns. This boiled down to three scenarios: “bad,” “worse” and “break glass.” The situation was unprecedented and no one could predict or fully anticipate the impact of COVID on the business in the coming weeks, months or years. My first challenge as CMO was to make an immediate, dramatic reduction in the marketing budget and realign the remaining budget and resources to drive the most efficiency and near-term impact. With the support of my new team, we made these changes quickly while closely monitoring the market, customers, partners and our business.
Within a couple of months, we discovered an increase in customer interest and demand for digital technologies. The COVID pandemic had driven consumers to digital channels and businesses began to increase investment in digital technologies in response. With this early insight, we pivoted once again but this time back to our original growth plans. My greatest lesson through this experience and a lesson that I plan to keep front and center at all times is to always be ready to pivot. Be ready to adapt quickly to the market, both in the growth times and at times of uncertainty, to your customers or consumers, because what might delight them today is going to change tomorrow, and to your competitors.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
One of the best leaders that I have ever worked for was early in my career while at Microsoft. I consider myself very lucky to have been a part of her team because she did not hire me. She was hired into Microsoft shortly after I joined and we immediately formed a great partnership. Patricia Ryan approached her role as the general manager and sales leader of a region as a “servant leader” putting Microsoft’s customers and partners first and building a culture of customer and partner-centricity. She invested time, energy, passion and creativity in transforming her leadership team into a high-performing team built on transparency, trust, accountability, teamwork and collaboration. She inspired us, her leaders, to become “servant leaders” to the employees in our organization by investing time and resources on employee morale and culture. I remember a time when Patricia convinced her leaders to serve all of the employees breakfast one morning to celebrate and recognize the hard work of our employees after we all achieved a big goal.
During the time that I worked with Patricia, she proactively looked for ways to invest in me by providing me with new assignments and creating opportunities for me to get visibility with senior leadership. When I had my first child, I was also at a point in my career where I realized it was time and I was ready to start a new role once I returned from maternity leave. Patricia was extremely supportive of my career and let me know that I could remain in my current role for as long as it took me to find the right next role. She also worked behind the scenes to recommend me for a promotion to Director. This was an incredible boost to my career and one that helped propel me forward when I returned from maternity leave.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
When I was a young girl, I believed that I could do anything I wanted and set my mind on when I grew up. I also believed that I could have it all — a career, a family and a full life. I had bought into the Wonder Woman Myth. I had to learn the hard way that it was impossible to do it all yourself without killing yourself. Having kids and a career has taught me or led me to the realization that you can’t do it alone even with a solid, supportive partner. I have reached out to others, asked for help and assembled a village to support me and my family.
A boss of mine once gave me a very value piece of advice. It was at a time in my career when I was feeling a bit “stuck.” I had been feeling stagnant as a result of being in the same role and level for a few years. I was frustrated that neither my boss or other leaders were helping my career along. During a career discussion with him, I shared my feelings of frustration. He was surprised by what I had shared and said, “Bridget, you should realize that I am not a ‘mind-reader’ nor is anyone else that I know.” His advice to me, which I took to heart then and put into action ever since, was to “just tell people what you want.” What I have come to learn is that the best way to get to where you want to go is to know what you want and then share it with others.
When I was earlier in my career, I remember feeling fear or anxiety when I was approached with challenging, visible stretch assignments or new, big roles. I would expend a lot of energy coming up with reasons and convincing myself and others that the timing was off or they were not the right opportunities. When I look back now, I realize that these feelings were driven by a fear of failure. Where others saw opportunity, I saw risk. It wasn’t until my desire to grow, to take on more, to be challenged finally won out over my desire to avoid risk and play things safely. What I eventually came to learn was that the only real failure is not trying in the first place. In the process of holding myself back from these opportunities to avoid failure, I was failing myself.
I started in my first executive level role at a new company. I was both excited and anxious. I had read the book, The First 90 Days, a few years earlier and remembered the general premise. I had a short transition between companies so I didn’t invest the time in re-reading the book. I jumped into the new company and role and hit the ground running. I found myself immersed in the day-to-day right away and was running at a fast clip for the first several months. Rather than spend the time evaluating the current state, I was formulating a point of view as I went about operating my role. I remember a conversation with my boss after about 5 months when I was defending the work of my team. My boss said something that stuck with me not only in that moment but for years to come. She said, “Always remember, you aren’t hired to maintain the status quo.” Whenever I start something new, this guidance is front and center in my mind.
For a very long time in my career, I was very self-critical and evaluated myself based on what I did and the work I produced. My need to feel valued by myself, my bosses and the companies where I worked, led me to constantly push myself to work harder. If I experienced a brief dip or lull in productivity, I would feel anxious and a lowered self-esteem. The culture of the company where I worked at the time, reinforced the message that you were only as good or valuable as the work you produced today. After leaving that company, it took me a number of years to change my mindset. I worked with a personal coach who helped me see how destructive this thought pattern was to me as well as the people around me. He helped me realize that my value comes from who I am as a person not just what (or how much) I do. This coach helped me see and appreciate my own value.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
I would absolutely love to have a chat with Megan Rapinou. First, I played soccer when I was growing up. I was a part of the first cohort of girls who played women’s soccer following Title IV. Megan also plays for the Seattle Reign, which is my hometown professional women’s soccer team. But, the real reason I would like to meet Megan is because she is a confident, courageous woman who speaks out on critical issues related to equity, gender and race. She has not been afraid to express her views about the current administration and political environment in the US. She is using her platform to send the message that we all have a responsibility to make America a better place and encouraging everyone to exercise their right to vote. She is a leader and role model for many girls and women around the world including me and my daughters.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Bridget Perry of Contentful: Why You Should “Just Tell People What You Want” was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.