Having spent three decades in the marketing and communications industries, boasting additional experience in learning innovation, operational effectiveness, efficiency, and digital transformation, Cheryl Wipper has made her mark. She possesses a unique leadership attribute, the ability to view her organization as an outsider would. This perspective has helped her stay ahead of the curve, developing and implementing strategies well ahead of other professional associations.
As the Vice President – Content and Communications at the Association of International Certified Professional Accountants (AICPA) and Chartered Institute of Management Accountants® (CIMA), Cheryl is passionate about making companies better through excellence, innovation, and change. Cheryl has led her teams to win more than 150 awards for innovation and excellence across groups such as the IABC, PR News, PR Week, Stevies, Marcom Awards, Association for Women in Communications, PRSA, PR Daily and SABRE. She has also been named a Top Woman in PR. In 2022, PR News named her an Industry Innovator.
Find out more about Cheryl’s journey below.
Pushing the Limits
Cheryl was the first in her organization to recommend and utilize marketing automation, introduce customer experience, push digital personalization and customized communication, develop a global master brand strategy and architecture, and apply enterprise content strategy and a content supply chain approach to learning and product development. She had to convince her organization each time to be an early adopter of these trends, but she knew they would catapult them into more competitive market-focused positions.
Cheryl has also successfully led critical campaigns on organizational changes, thanks to the early adoption of trends. Throughout her career, she has pushed for change rather than reacted to it, understanding that industries and business models inevitably change and that it is better to help shape the future than to be at its mercy.
Cheryl Wipper started her career in academics, teaching college-level English literature courses with a specialization in Anglo-Saxon and Middle English. However, she realized one day that her career path was limited, and she would only talk to a small group of scholars throughout her academic career. This realization inspired her to apply the skills she learned as an academic in a business environment.
She was an excellent writer and a strong critical thinker, comfortable presenting in front of a room, and loved finding solutions to complex problems. One of her colleagues once said, “If something hard needs to get done, give it to Cheryl.” Cheryl found that the business world was an ideal fit for her because of her academic training, not despite it. She was always willing to enthusiastically tackle tough questions, impossible situations, and thorny issues.
Empowering Accountants
The Association of International Certified Professional Accountants® (the Association) is a global organization that represents both AICPA® and CIMA®. With 689,000 members, students, and engaged professionals in 196 countries and territories, the Association is the world’s leading organization on public and management accounting issues.
They achieve this through advocacy, supporting the CPA license, the CGMA designation and specialized credentials, professional development, and thought leadership. The Association aims to build trust by empowering its members and engaged professionals with knowledge and opportunities to lead in broadening prosperity for a more inclusive, sustainable, and resilient future.
Cheryl’s team is critical to achieving the organization’s purpose, value and vision. She makes sure her team members, no matter their level, understand and can explain their contribution to the organization. Work that has a purpose, she believes, is more meaningful and relevant and when employees know that and connect their individual work with it, they are more engaged, loyal and committed to excellence.
With such an important role to the organization, Cheryl pushes innovation constantly. Never say “this is the way we’ve always done it.” She seeks to rethink and reimagine with the goal of always delivering at higher and better levels.
Cheryl enables this approach in the organization through established norms for behavior and culture centered around trust, respect, and standing up for what is right. It encourages assuming positive intent, having necessary conversations, and supporting diversity, equity, and inclusion. Their culture values innovation and continuous improvement, which has allowed Cheryl to lead several changes successfully. These established norms for behavior and culture help the organization to maintain a positive and productive work environment that encourages employees to feel valued and motivated to contribute their best efforts.
Cheryl also points out how important relationships are, especially as employees move up the ladder. She encourages her employees to identify champions that can help them achieve audacious goals. Champions, she believes, are different from friends. Friends are important, of course. But champions support an individual’s or team’s vision and help move it forward even when obstacles prevent progress. She also advocates for managing one’s emotions in the workplace. We are all human, but being able to remain calm, focused and self-observant during conflict enables quicker resolution.
Making the Difference
In 2020, Cheryl took over learning development for her organization and became a student herself to understand the market they serve and have a customer view. Cheryl identified enormous opportunities to transform the learning and product offerings. She led her team to apply a new journey-based learning methodology, new tools, and technologies and implement adaptive and generative AI features.
The group launched a new learning delivery system that provided deeply interactive and personalized learning experiences, which is still an ongoing project. Cheryl’s understanding of the complexity of the accounting and finance profession, along with her vision for innovative learning, helped her guide her team toward success.
Cheryl believes that a positive work culture is essential for employees to thrive. That is achieved by enabling them to share their opinions, and test and learn without fear of being penalized for their mistakes. She values diverse perspectives and encourages her team to speak out, challenge respectfully, and push the boundaries of innovation.
She believes that this approach fosters employees who are passionate and fulfilled by their work. Cheryl also understands the importance of work-life balance and honors her employees’ boundaries by rarely contacting them outside of work hours. She strives for a whole-person approach to leadership, recognizing that employees bring their whole selves to work, and it is vital to respect that.
Implementing Future Tech
Cheryl Wipper recognizes the rapidly changing nature of the business world and the impact of technological advancements on the accounting and finance profession. With the advent of generative AI, roles once deemed exclusive to humans are now being automated. While she acknowledges the potential benefits of such technology, she also highlights the importance of being cautious in its application.
As the head of a team that develops content for the accounting profession, she encourages her team to experiment with generative AI but also to be mindful of the risks, ethical considerations and legal implications of this technology. Because her team authors most of the organization’s content, she works hard to make sure her team champions and maintains its originality, authority and voice. After all, she says, “We are speaking on behalf of a learned profession. As its steward, we are trusted to represent it with authenticity and accuracy.”
Cheryl predicts generative AI will be the most significant learning, content, and creative output disrupter in the coming years. Several possible scenarios could play out: it could replace human capabilities, be used for efficiency gains, or make human uniqueness even more valuable. Cheryl believes it’s essential to drive the change rather than react to it to stay ahead of the curve. And for that reason, she advocates for the tool to complement and inform rather than replace human outputs. Her team will continue to identify generative AI’s place in their organization and use it to enhance human capabilities and improve speed to market. In other words, technology doesn’t have to be a disruptor. It can guide professionals to deliver better and more efficient work.
Bequeathing Guidance
Cheryl advises aspirants willing to venture into modern business to get comfortable with change. She says, “While others are scared of change, you can remain objective about its impact- and that puts any professional in a place of growth.”
“Be willing to hear perspectives different from yours. Being right rarely builds growth. But learning from others and building relationships by wrestling through differences leads to success,” Cheryl concludes.
The Success Story
Early in my career, I read a book about learning that defined learning as a “spiral of disequilibrium.” Basically, the theory says, learning is a place of discomfort, and you will be uncomfortable and off-balance until you gain mastery. This resonated with me and I have used it as a measurement of growth ever since.
This commitment to growth led me to continually- and I still do it- put myself in places of discomfort. I always took the biggest, hardest projects- the projects no one else wanted because it scared them. It scared me too. But if I was going to grow, I had to take them.
About 10 years ago, I attended a leadership retreat where we practiced leadership by working with horses. I hadn’t been near a horse in over 30 years, so I was plenty uncomfortable being around horses. My colleagues picked the smaller horses- the ones they felt they could manage. If you’ve ever been around a horse, you know that horses respond to unspoken authority and leadership. The sense your stance in relation to them and respond to it.
When my turn came, without even thinking, I chose the biggest horse. He a Belgian horse standing around 15-16 hands. And he scared me. But I wanted to test myself. Could I make this horse walk around the pen with me?
Now, you can’t tug on a horse to make it go. You take the rope, and you walk with certainty. That sends the message- follow me. And that’s what I did. At first, he didn’t budge, but then he began to walk. Around the pen we went, my heart thudding in my chest. He followed.
After this was over, the executive of the team I was on came over to me. She said- I watched you choose the scariest horse in here, and it dawned on me, this is what you do at work. You choose the scariest horses.
And indeed, I do. I have led enormous projects that others couldn’t complete- most recently a reorganization that resulted in my leading a team of 244 people. That was a year and a half of discomfort. But at the end of it, I was promoted. It has been just a year and a half since that promotion, and I am still building a brand-new team in a zone of discomfort.
