Investment Banking To How This General Manager Landed Executive Roles At A Young Age

By Cheryl Robinson

Family caregiving is on the rise in America. In 2020, Zippia reported that 57% of working families spent more than $10,000 on child care, and on average, Americans with children spend at least 10% of their household income on child care. Also, according to the National Alliance for Caregiving, the 2020 statistics reveal an increase in the number of family caregivers in the United States of 9.5 million from 2015 to 2020. Family caregivers now encompass more than one in five Americans. As a result, families are in dire need of help when caring for their families. 

Natalie Mayslich, general manager of consumer and enterprise at, is responsible for expanding, building and delivering the company’s portfolio of childcare, senior care and employer-focused products and services. As part of the sandwich generation with caring for her father and her own children, she understands the importance of quality care, which translates into her work. 

“What we’re seeing is a general trend by companies to have to be more caring companies, particularly with Covid,” Mayslich explains. “Also, how do we have the conversation and ensure that our peers and companies around us are aware of how important care benefits and a supportive caring culture are to the growth of their employees and the continued employment of their employees? … I’m incredibly empathetic to our employees. Leading by example is really important. So taking your maternity leave, ensuring you’re employing those care benefits, all of those things are actually difficult to do. As a general manager, I often don’t want to [take time off from work] because there’s always another thing that we can be doing, but showing that it’s okay to do that, and expected and welcomed is important.”

Mayslich began her career in investment banking at Jefferies & Co. She worked within digital media and technology but quickly realized she wanted to be hands-on operating. She transitioned to Viacom before landing a role at Time Warner Investments as a venture capital associate. She sat on a couple of minority board roles and enjoyed the board observer roles. The closer she worked with the CEOs and businesses that the company invested in, the more she knew she wanted to work on the operating side of the house. 

She intentionally made it clear to her network what she actually wanted to be doing. “If you don’t ask, you don’t get,” Mayslich stated. “I’ve always felt like every move needs to be incredibly intentional and planned, and cultivating the help of your network and the points of view is important. … For me, it’s less about being courageous in these conversations and more so about who do I actually want to seek counsel from, and have those conversations and move my personal objectives forward.”

She pivoted to IAC, a media company home to more than 150 digital products and brands, where she held various executive roles, including chief financial officer for CollegeHumor, where she oversaw finance, strategy, partnerships and growth operations. She was instrumental in launching the company’s subscription business, which she helped grow to over 100K subscribers. Additionally, Mayslich ran its programmatic advertising, commerce and live-events business lines which grew to represent more than 30% of its revenue.

“I would be willing to raise my hands and take on more as the business allowed,” she explains. “It was very much about asking questions, being curious whether it was within my role or outside of my existing role, and offering a view when I had one.” 

When IAC sold CollegeHumor, Mayslich joined the team as general manager of senior care. As she made that pivot, she dealt with finding care for her ailing mother, who was her primary caretaker to her three children. She also had to find a nanny for her children. Her care challenges have helped her structure the products and streamline the customer experience. Then, one year later, she stepped into her current post. 

As Mayslich continues to evolve in her career, she focuses on the following essential steps:

  • Be clear in what you want your next move to be. Create a strategy with the end goal at the forefront. 
  • Check in with your network and trusted advisors. We’re all impacted by prior experiences. Ensure that your prior experiences are reflective of reality and that you’re really going to get what you need.
  • Schedule frequent intakes on how the pivot is going. Is it aligning with your personal mission? Are you meeting those small manageable goals? What do you need to adjust in your strategy? 

“In my first town hall as general manager running our consumer enterprise business, I was thinking about how do I really start to build trust?” Mayslich concludes. “How do I ensure that employees are comfortable working with me in this new capacity? So I decided to share my personal care story, a little bit about my mom and a little bit about how difficult it was shepherding the CollegeHumor employees through a public sales process. Ultimately, it wasn’t the best. It wasn’t a great outcome for the business, not what we wanted. So sharing a personal failure and how we grew from that failure really changed the game for me and cemented a trust that enabled us to structure a roadmap, increase the velocity of our teams and allocate capital in a smart way.”