Chief of Staff to CEO

New York City
Jun 10, 2021
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About Upsolve

Upsolve helps low-income families in financial distress access their legal and financial rights, through tech products, community, and education. Our mission is to fight for a legal and financial system we can all access. Our first product, a web app that helps families file for bankruptcy for free, has relieved $300 million+ in debt for low-income families suffering from medical bills, predatory loans, and layoffs. Today, Upsolve has 150,000+ members. Named to TIME’S 100 Best Inventions of 2020. Upsolve is fighting for racial, economic, and social justice at scale.

Upsolve is funded by Y Combinator, Jack Dorsey, Eric Schmidt, the Robin Hood Foundation, Jim Breyer, Vinod Khosla, and Chris Sacca, the Hewlett Foundation, the Legal Services Corporation, and several others. To date, we've raised over $6 million.

Hear from our users about the difference Upsolve has made in their lives and watch our recent TED Talk, sharing our work and our vision for a more equitable legal and financial system. Please read this post to learn more about where Upsolve is headed in the long run and how we see our advantages compounding over time: Understanding Upsolve.

The Role

**As Chief of Staff to our CEO, you’ll operate as a fast-moving generalist who tackles a wide range of projects. **You’ll work on internal company functions like goal-setting, content, and finance. You'll also lead specific projects across recruiting, public relations, fundraising, and business development. You’ll be a ‘doer’ who takes on anything that the company needs done to move forward - no matter how glamorous or mundane the project.

We’re a small team and we’re moving fast – you’ll have a big impact on our success and an opportunity to see all aspects of the company.

What You'll Do

  • Take on a variety of projects to help our CEO
  • Help lead departments that don't already have department heads
  • Research fundraising prospects and conduct outreach
  • Develop ideas for news stories and pitch Upsolve to the media
  • Source and screen candidates for unfilled positions
  • Develop partnership ideas and lead outreach to nonprofits, government agencies, and private companies
  • Develop strategy, conduct outreach, and build coalitions for our advocacy campaigns
  • Work with our content team to develop ideas for educational articles
  • Support our efforts to deepen relationships with existing donors and report our progress
  • Collect Upsolve user stories to share with funders, the media, and our partners
  • Analyze and share user data with the entire Upsolve team to track impact over time
  • Collect OKRs from specific departments and measure progress
  • Work with our bookkeeper and accountant on our financial statements
  • Plan team-bonding activities and weekly all-hands

Who You Are

  • You’re **an effective multi-tasker who gets things done **- you know how to prioritize and you thoughtfully complete your to-do list
  • You’re an analytical and creative problem-solver - you can break down new problems, compare options, and come to decisions that are based on thoughtful analysis and creativity
  • You are low ego - you relish the opportunity to work on all aspects of the business, no matter how big or small
  • You’re **driven by our mission **- you are highly motivated by our vision to create a legal and financial system we can all access
  • You are a **fast writer and persuasive communicator **- you're able to conduct high quality, high volume outreach to different organizations, funders, job candidates, media outlets, etc., and once you’re on the phone, you excel at sharing the Upsolve story
  • You’re **ambitious and optimistic **- you’re keen to tackle big challenges, bit by bit
  • You want to **have fun **- you want to celebrate the wins with us
  • You are **absurdly persistent **- every “yes” may be accompanied by 10 “no’s” and 20 non-responses – you are someone who is extremely persistent about follow up
  • You have an interdisciplinary theory of change - you are equally excited by the tech startup part of Upsolve and our social justice advocacy


  • 5+ years of experience in a business role (e.g. finance, consulting, strategy, etc.)
  • Experience at a tech startup or similar fast-paced organization
  • Experience with analysis and managing projects
  • Must have a concrete track record of fighting for social, racial, or economic justice
  • Must be based in NYC

How to Apply?

To apply, please email two things: (1) a bit about yourself and why you feel like you'd be a good fit; (2) your resume. Be sure to include "Chief of Staff application" in the subject line. We read every email even if we don't reply. We'll be in touch within two weeks if we think we may be a good fit.

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