In this enlightening episode of Thriving in the Messy Middle, host Amy Wilkins welcomes Kelly Wenzel to explore thriving in the challenging “messy middle”. Kelly, with her rich experience as a seven-time CMO in the tech industry, offers a unique perspective on balancing professional growth with personal values and responsibilities. The episode dives deep into the challenges faced when navigating career progression, the importance of a robust support network, and the role of authenticity and integrity in leadership.
Kelly reflects on key moments from her career in B2B technology, discussing the subtle challenges faced as a woman in the C-suite and the strategies she employed to navigate these experiences. She emphasizes the necessity of building strong relationships, both professionally and personally, to combat self-doubt and drive transformative change. For those navigating transitions, Kelly’s candid stories and practical advice offer guidance on embracing vulnerability, setting clear intentions, and trusting in personal growth and evolution. Discover how these strategies can transform your leadership journey.
Key Takeaways
- Navigating Leadership Spaces: Embrace authenticity and integrity in leadership, focusing on open communication and honest assessments to guide teams through transformation.
- Building a Supportive Network: Establish a personal board of advisors, or a network of batteries, to energize and guide you through career challenges and self-doubt.
- Career & Personal Life Integration: Successfully managing career and family is possible but requires intentional decisions and support systems.
- Embracing Change and the Unknown: Stay open to opportunities despite self-doubt, as unforeseen opportunities can lead to significant career advancements.
- Resilience through Adversity: In moments of personal or professional hardship, allow space for emotions, rely on your support network, and refocus on future goals with clarity of purpose.
Kelly Wenzel Quotes
“There are two types of people in life. Some people charge you up; those are your batteries. And the people who weigh you down, those are your anchors.”
“You cannot give in to self-doubt. You are always going to have those voices that are trying to tear you down, and usually, they’re your own.”
“Identity, actions, feelings. Start with identity. Who do you want to show up in the world? Who do you want to be?”
“The mess always comes before the morph, right? Like, there’s always great change that’s coming on the other side of that mess.”
“Nothing shifts your attitude like gratitude.”
Mentioned in this Episode
Batteries and Anchors, LinkedIn article by Kelly Wenzel
She Runs It, visit the website for more information about the organization focused on women in marketing, media, and tech
Books by Daniel Pink, particularly “Drive,” which discusses motivation and achieving goals
The Unwritten Rules of Women’s Leadership by Helen Appleby
The Fast Forward Group, learn about creating vision statements and other leadership tools
Fast Forward – 5 Power Principles to Create the Life You Want in Just One Year, book by Wendy Weshgold and Lisa McCarthy, CEO and Co-Founder of the Fast Forward Group
The 8 Steps for Leading Change E-Book by Dr. John Kotter
Visit the Kotter website to learn more about Kotter’s methodology
About Kelly Wenzel
Kelly Wenzel is the Chief Marketing Officer at SmartBear, where she leads global marketing efforts and oversees the go-to-market strategy. She brings over 30 years of marketing leadership in both fast-paced startups and scaled global enterprises, including Amazon Pay and Amazon Alexa. Now a seven-time CMO and career B2B tech leader, Kelly has a track record for building and scaling growth engines based on operational discipline and a relentless drive to improve marketing performance. Kelly is a builder and a recognized change agent, known for building rock-solid teams, processes, and infrastructure. Kelly’s accolades include being named a Working Mom of the Year and being honored for her executive leadership and brand initiatives. She has also contributed significantly to the advancement of women in tech through her board position with “She Runs It” from 2016 to 2021. When she’s not working, she’s either working out (maintaining her Peloton streak), spending time with her husband and 15-year-old twins, or getting walked by their 150-pound bull mastiff, Evie.
About Amy Wilkins
Amy Wilkins is a leadership coach, former media executive, and the founder of Choose Awe—a coaching practice devoted to helping women leaders navigate transitions with clarity, courage, and self-trust. After decades in senior leadership roles, Amy now empowers women to lead with purpose and thrive through the “messy middle” seasons of life and leadership.
Schedule an Exploration Call HERE
Read The Messy Middle Blog HERE

