Chief of Staff

Job Description

FreeWorld is seeking a detail oriented, self-driven, adaptable, get shit done Chief of Staff to work with FreeWorld’s Founder/CEO. The Chief of Staff will help with a range of priorities from helping with fundraising to assisting our Head of Operations with scaling FreeWorld across the nation. The ideal candidate can work at a high level, but is not afraid to sweep the floors (no ego). You are hungry to learn, data driven in your work, and meticulous. You are incredibly organized and an excellent communicator. You are the CEO’s right-hand person and a force-multiplier. Above all, you are incredibly passionate about our mission and believe that everyone deserves a legitimate second chance. 


To end the era of mass incarceration and generational poverty by:

What you’ll do

Preferred Experience

Where you’ll work

The Bay area is preferable because you will be working very closely with our CEO, but we are open to hiring anywhere in the United States. FreeWorld is a 100% remote company. 

Board of Directors

Matt Mochary  - Serial entrepreneur, VC, social entrepreneur, CEO coach
Jason Green  - Founder - Emergence Capital, Endeavor, Kauffman Fellows
Andy Bromberg  - Co-Founder and President - CoinList
Jason Wang  - Founder/CEO - FreeWorld
Michelle De La Isla
- DRK Managing Director

Hiring Process

  1. We have a 15 minute introductory call. If we love each other, then…
  2. You read all of this documentation and sleep on it. If in the morning, you are still super-excited then…
  3. You write up a 1-page version of an Issue / Proposed Solution about a real issue in your life. To understand how it works, please read Decision-Making (8min).
  4. You talk to other members of the team.
  5. We talk again to go through your background for me to know who you worked with. 
  6. We agree on terms, pending references. I talk to a few of the folks that you worked with. 
  7. We start working together on a 30-day contract. If we both think it’s a fit, this moves to a full time role. 

Compensation and Benefits

The compensation for this position is based on experience, but we are targeting $120k - $140k.