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Hypepotamus – Get To Know The CMO: Lessons Learned From Moving Into Startups From Holly Wasson

by | Oct 10, 2022

Holly Wasson Headshot.

Originally posted on Hypepotamus by Maija Ehlinger on October 6, 2022.

There are people who spend their entire lives in the “startup land.” But after 20 years in corporate America, Holly Wasson joined her first startup in 2018 because she found a platform that was solving the very real problems she experienced in the marketing departments at large companies.

Wasson cut her teeth at Turner companies like CNN, TNT, and TBS before moving into the agency and consulting side of marketing. That move, she told Hypepotamus, was about finding more work-life flexibility. It was during this time that she met Atlanta-based entrepreneur Stephanie Nadi Olson who was building a platform just for professionals like her.

“Steph and I met for lunch and I immediately fell in love with her vision,” Wasson said. “We had similar paths where [Steph] had left the corporate world after an extremely successful career…and she knew women and people of color were flooding out of the advertising industry. They just didn’t feel like it was set up for them.”

Olson’s vision launched We Are Rosie, a platform that connects advertising and marketing professionals with companies in need of outside help.

Wasson started as one of the first “Rosies” — independent marketing contractors found on the platform — but ultimately moved onto the full-time team as the startup hit hyper-growth mode.  She is now We Are Rosie’s Chief Community and Marketing Officer, where she is responsible for the growing number of “Rosies” and companies on the platform.

While very much in the trenches of an early-stage startup, Wasson said she is leveraging her corporate experience to expand We Are Rosie’s customer base.

“The best part is that I am able to take my over 20 years of knowledge and apply it to a company while not having to get sucked into the politics and distractions that just pop up….it’s freeing,” she added. “I can go in and talk to marketing executives and let them know I understand where they are. I know how hard it is to get talent. I know the frustration of working with some of your agencies.”

Lessons Learned Along The Way 

The day-to-day life of someone in corporate America can look very different than what an early employee at a startup might experience. When Wasson reflected back on her jump from working at Fortune 500 companies to early-stage startups, she observed three key differences.

First, startup employees have to “fail forward” and quickly analyze the data in front of you…a skill not always celebrated at larger corporations.

“In large, matrixed companies, this trait is not always appreciated as it is important politically to make sure that you move slowly enough to get other departments to not only understand the move, but agree with it before you can proceed.  Sometimes even if it is the right decision for a large organization, politics will get in the way of executing upon the idea. When I was in a large organization, I received feedback that I was able to quickly review data and understand what needed to be done and was too willing and ready to move forward before “making sure everyone in the organization was on board the train before it left the station.”  At a start-up, my ability to make quick, research informed decisions has been a benefit. There are no politics to slow us down.  Everyone here wants the best for the company and is ready to move,” she said.

Secondly, she said it was important to really embrace flexibility at all levels. “In a hyper growth start-up, the team needs to be willing to iterate, iterate, iterate,” she added. “We cannot stay married to our old ways of doing things.  Growth and the ability to scale as we bring on more and more Fortune 500 clients requires constant process, tech and talent expertise enhancements and additions. Flexibility is key to our success.”

Finally, Wasson said her move into startups made her realize just how important it is to establish clear-cut goals. She said these are to “rally the team and allow leaders to empower employees to work towards our common mission autonomously. There is no need for or time for micro management in a start-up. Growth depends on hiring experts to bring their magic to the table and put that magic to work quickly to benefit the company.”

Where We Are Rosie Grows Next

Wasson isn’t the only one that sees high-growth potential in We Are Rosie. The Atlanta-based startup raised a private equity round from Dallas-based Align Capital Partners in late 2021. The growth investment puts the platform’s valuation at $110 million.

Wasson, who has now been at We Are Rosie for four years, said that in the early days the company was motivated by “a sheer desire to change the industry and things that we didn’t like about the industry.”

Now, the platform has an impressive 18,000 marketing professionals using the talent platform to find more meaningful, flexible jobs in marketing and advertising.

“We know that it is extremely important for independent marketers to connect with others to help them grow in their careers,” Wasson added. “We are showing that remote work is a form of inclusivity. We are showing that independent marketers can continue their careers and grow their careers but do it in a way that works for them.”