Leadership Lessons from Cheryl Porro

Cheryl Porro has recently announced that she’s moving from her role in executive leadership at Salesforce.org to a new organization, Thrive Global. I met this news with mixed feelings - happiness for my friend and her new opportunity and adventures, and sadness that Salesforce.org is losing such a dynamic, passionate, and talented member of the executive team.


I remember the day I met Cheryl Porro. She had just come to Salesforce.org as Senior Vice President of Technology and Products. She definitely came from an office with a door, and was therefore intimidating to me - a partner new to the Salesforce.org space and new to technology. I knew who she was, but I assumed she didn’t know me, the random partner who was trying to get a nonprofit serving women and underrepresented voices in technology off the ground. She introduced herself to me at Dreamforce in 2014 and rather than asking for the stats on our company and what I did for them, she asked me who I was, where I came from and what my passion was.

Conversations at Dreamforce as notoriously rushed, but she stood there talking to me about cupcakes and nonprofit work and Amplify (then Girlforce), and listened to me talk about the amazing nonprofits we worked with and how much I loved my work. She told me about her daughter and about the pair of flats she kept in her oversized handbag because the 3” heels she was wearing wouldn’t cut it on the street walking home. She told me about bringing cupcakes to a job interview, about connecting with people, and about being an engineer and what that meant to a woman in a man’s field. It was an organic conversation that didn’t feel rushed or like she had somewhere else to be. Her entire attention was focused on me, and on the space we had created between us. I walked away from meeting her with her business card and her personal email (which she told me to use anytime I needed anything, or if I just wanted to talk),  thinking “Oh my goodness, I’ve just met one of the most amazing leaders of my life.”

Fast forward a year to Dreamforce 2015, and Amplify was having its third annual breakfast gathering. It had been a hard year: I had been overworking and over-stressed. Although my work and nonprofit were thriving, my personal life and mental health were on the rocks. I had been struggling with depression and anxiety, feelings of not being good enough overshadowing my success. Past failures and trauma had risen to the surface, increasing my feelings of fear and shame. I had reached the end of my rope and I was holding on for dear life- and then I let it go. I fell (quite ungracefully) and landed in a mental hospital where I worked on my depression and fear and shame with other broken people. When I returned home, I knew there were changes that needed to happen in my life, the most important of which being that I couldn’t hide myself anymore. I began to talk to my close friends and co-workers about it. I began to write about it.

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When Dreamforce came around, I knew I would be speaking to Amplify members and I also accepted an invitation to talk at the nonprofit community theater at Dreamforce. I decided that instead of telling a story of how to build community in Three Easy Steps, I would tell the story of how to rebuild yourself in three really hard steps. Instead of talking about technology, I would talk about my journey, and the human experience.

I stood at the front of a packed room for the Amplify breakfast, my remarks prepared and written on paper. I thanked everyone who was present: all of our partners, our board members, and our supporters and members. The room was full of my business associates: partners, competitors, customers, future customers and folks from all levels of the industry. Standing directly in front of me on the front row was Cheryl Porro. When I began to share my story, with a quavering voice, my hands shaking, she stood there willing me to have strength in the telling. She listened, just as she had that first day when we met, and with her encouraging smiles, she made it seem as if I was just talking to her. When telling my story caused tears to form in my eyes, her eyes filled too. And when the story was through, she clapped and clapped and stepped forward to give me a hug. “You are so courageous, Joni.” She said, “I don’t know if I could have done what you just did. I’m so grateful that you broke yourself open for us. Thank you.”

I didn’t feel courageous that day. I felt afraid. I felt nauseous. I felt ashamed. I felt like I was committing career suicide. But hearing that from Cheryl, a leader I admired and respected and a friend and mentor to me, actually did a magical thing: it filled me with courage. Courage to tell the story again to a wider audience of mostly strangers. Courage to take back and own my narrarrative. Courage to bring my whole self to work, even the parts that I viewed as unfit for the ‘perfect’ professional woman.

Cheryl taught me a number of things about how to be a leader over the past few years of working in the same space. Some of those things include:

  1. Great leaders lead with heart.

  2. Great leaders prioritize connection and relationship with people, regardless of their level or status, because they believe that everyone has something to teach.

  3. Great leaders take time to mentor others.

  4. Great leaders prioritize their own health and well-being.

  5. Great leaders create a culture where failure is treated as a learning experience.

  6. Great leaders admit when they need to pull back and regroup.

Most of all, Cheryl taught me that great leaders bring their whole selves to work - even the imperfect parts. They know that their experiences and failures made them better. They make a space for being human on their teams and in their organizations.

We will all miss Cheryl as she heads into her new adventure, but, if I have learned anything about my friend and mentor, it is that she won’t leave the relationships behind. I’m wishing her all the best things in her new endeavor!

Joni Bryan is a Senior Consultant at Now IT Matters, and the Co-Founder of Amplify.