Sept. 14, 2022

Episode 162: Gillian O'Brien

Episode 162: Gillian O'Brien

Gillian O'Brien

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Show Notes

Disruptive CEO Nation Podcast with Allison K. Summers

Episode 162 Gillian O’Brien

Gillian O'Brien, Founder in Residence, Pilot, California, USA - Why companies can benefit from a Founder in Residence and why being loud about failure can lift up the startup community.  At 27, Gillian has had more adventure in her career than others do in a lifetime. 

Pilot serves over 1,000 customers who are founders and business leaders with their accounting, finance and accounting needs. Having a Founder in Residence helps deliver insight, empathy, and meaningful ideation for their customer base. Pilot has a staff of 400 people strong and is valued at over a billion dollars.

In our conversation, Gillian O”Brien explains:

  • Her experiences at Y Combinator and why founders need a community of supporters.
  • Her first startup Cherry, an HR Saas business, and her willingness to be public and 'loud' about lessons learned in failure as she had to shut down the company at the beginning of the pandemic.
  • Understanding resources needed by founders and helping them with investor conversations.

Be sure to check out Gillian’s listed below.  Enjoy the show!

Connect withGillian



Connect with Allison:


#tech #SAAS # business #designthinking #AI #creativesociety #teambuilding #CEO #startup #startupstory #founder #futureofwork 

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