Chief of Staff - Head of Operations

New York, NY
Dec 18, 2021
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Bring a modern learning system to the world.

Work closely with the CEO to build and scale the community college system of the future.

ShiftUp seeks its first full-time hire, a CoS/Head of Ops, who will own business operations and build and manage the team to help make it happen. This is a remote-friendly position for candidates located +- ~3 hours from US Eastern Time. CEO is based in NYC.


ShiftUp is on a mission to strengthen lives through accessible and effective education.

Accessible online training (flexible, low-cost) often isn't effective, and effective training often is expensive and inflexible.

ShiftUp has created a middle path. We provide virtual + physical wraparound support for online learners, with a focus on serving low-moderate income adults. Our "learning gym" model combines affordable, flexible course materials with high-touch mentoring and support.

ShiftUp launched our first learning gym in-person in 2019, pivoted online during COVID, and is now expanding nationally in partnership with the world’s leading online learning platforms. Our programs are fully paid for by the government for any eligible Michigan resident, a benefit we will replicate across other states and countries.

What You'll Do

You will work closely with the CEO during a critical early-stage expansion phase as a key operations and strategy partner.

  • You will own day-to-day business operations for the company -- ensuring we set and meet ambitious KPIs and that the metaphorical trains run on time, every time.
  • You will build and manage your team to help you do this.
  • You will own or co-own management of contractors, employees, and back-office (legal, finance/accounting) business teams.
  • You will support investor relations through the preparation of decks and financial models.
  • You will oversee business ops infrastructure development, including systems to support recruiting, HR, admissions, student support, career services, investor relations, & more.

Candidate Qualities, Experience & Skills


  • Track record of operational excellence in a startup environment, likely 3-5+ years relevant experience in mid-senior level roles
  • Proven ability to build and manage exceptional teams
  • Ability to create order from chaos and efficient systems from jumbled processes
  • A founder mentality, switching between strategy and execution with ease
  • Desire to learn, analyze, and execute quickly


  • Familiarity with the higher education tech / innovation industry
  • Management experience

Our Principles

  • Respect the head, the heart, and the hustle
  • Don't take life too seriously... because no one's getting out alive! :D
  • No BS


Competitive salary + equity for comparable early-stage funded companies

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