In The Room with SJ Sacchetti

In this week’s episode of The Room Podcast, we sit down with SJ Sacchetti, CEO of Cleo, the working parent benefits platform for employers. Her journey is unique in that becoming CEO was not planned; in fact, she started in the political sphere with campaign fundraising then moved to tech as a marketing consultant. SJ eventually became SVP of Marketing then CMO of Collective Health, a business in the middle of how healthcare is paid for in America. After 5 years at Collective Health, SJ joined Cleo as CEO in late 2019. In late March 2021, Cleo announced a $40 million Series C round.

Madison and Claudia chat with SJ on key themes, including leadership during unfamiliar and unusual circumstances, overcoming imposter syndrome, and being a boss amidst uncertainty. Let’s open the door.

Season 3 of The Room Podcast is sponsored by Silicon Valley Bank and Cooley LLC.

Key Theme 1: Leadership during unfamiliar and unusual times

When Cleo approached SJ in the CEO recruiting process, she wasn’t sure that this was the job for her. She wanted to remain an involved mom while still making a meaningful impact on people’s lives in her career. There were also few examples of women doing this successfully. However, what SJ realized was the following:

“When I realized that the opportunity was to shape the product and the team to support that, and essentially practice what we preach was being handed the Rubik’s cube and saying, well, if you solve this here, you might be able to create that carbon copy for many more companies and women to follow.”

Key Theme 2: Overcoming imposter syndrome

Even though SJ believed she was done with the feeling of imposter syndrome, it has creeped back in her life. SJ feels a constant undercurrent that everyone else seems to know what they are doing and what is coming next. Her self reminder is that the word startup is synonymous with the fact of not knowing what’s next. Talking about it, however, is an important task as it’s a common feeling amongst startup founders and executives.

Key Theme 3: Being a boss amidst uncertainty

SJ joined the Cleo team only a few months before the onset of the Covid-19 pandemic. Being a CEO at this time has undoubtedly brought its challenges for SJ, but at the same time, it has taught her valuable lessons in leadership. With a virtual working environment, SJ lost a certain connectivity with her colleagues. However, during the virtual Series C process, SJ uncovered some of the bigger strategic pieces for the business, including involving the team even earlier in big projects. SJ views these as learning curves realized due to the unique situation of the pandemic.

Thank you so much to SJ Sacchetti for joining us on The Room Podcast. The episode is now live on all podcast streaming platforms. See you next week for a new episode at 7AM PST on May 17.



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