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Chief of Staff

San Francisco, CA
Oct 14, 2021
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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:

  • Placing returning citizens into high wage careers at scale.
  • Developing a self-sustaining revenue model to accelerate our growth. Today, we are using income share agreements.
  • Creating systemic change by leveraging our incredibly deep layers of graduate data in partnership with the Criminal Justice System to become the Gold Standard for re-entry.

What you’ll do

  • Ensure the CEO is working on the most important activities for the organization
  • Help complete priority items for the CEO with high quality
  • Keep the CEO accountable for commitments, while helping keep reports accountable for results
  • Keep the CEO accessible and open to new ideas and proposals
  • Act as a swiss army knife: lead a metrics overhaul, do customer researcher, build partnerships, help QA tech, lead our PR/marketing, help design the structure for government sales
  • Write and submit grant proposals

Preferred Experience

  • 1-3 years of experience working in an early stage startup organization (<50 employees)
  • 1-3 years of experience working at a top management consulting firm
  • 1-2 years of experience working in tech
  • Impacted by the criminal justice system (not required)

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.

  • Remote work flexibility
  • health insurance, dental, and vision coverage
  • Unlimited PTO
  • Fun, fast paced environment
  • Creating tremendous impact at scale
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