Head of Finance


Full Time Executive-level / Director
Outschool, Inc. logo
Outschool, Inc.
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The Company
Outschool's mission is to inspire kids to love learning. We achieve this by linking learning to kids’ interests, connecting them with other classmates who share their passions, and giving them the autonomy to pick their own paths. Our small group classes meet over live video chat with teachers who celebrate their unique strengths and empower all learners to develop confidence and a strong sense of self.
We're also focused on removing barriers for historically underserved learners who face systemic challenges to their success. In 2020, we started Outschool.org and began offering financial assistance to families in need. We are currently creating an Educator Endowment Fund to appreciate the teachers who are so central to our mission of inspiring kids to love learning.
We believe that diversity drives learning. To meet our mission, we encourage, support, and celebrate different ideas, perspectives, and backgrounds. As a fully distributed (remote) team, we challenge one another to find the most effective way to empower learners, teachers, and parents. Your name, race, religion, gender, nationality, sexual orientation, and age are not barriers; they are why we want to work with you. We invite talented and creative candidates who value the importance of nurturing a child's boundless curiosity to join us on this journey.
The pandemic has been challenging for families all over the globe. We acted quickly and worked together to provide quality resources to learners, parents, and teachers in the past year. As communities worldwide rethink their approach to education, Outschool will continue to innovate and provide kids with unique opportunities to explore their passions.
Earlier this year, Techcrunch recognized Outschool as the newest EdTech unicorn. We've also been named Fast Company’s most innovative EdTech company in the world, and one of the top ten best startups for women from Elpha.

The Role
Outschool is looking for a strategic, impact-seeking Head of Finance to join our executive team and guide us through the next stages of our growth through an IPO. We’re looking for a candidate with a track record of building world-class Finance teams, shaping a company’s financial strategy & operations, and serving as an executive. You will join Outschool at a stage of significant growth and investment, and will be responsible for building the financial foundation that enables us to effectively scale our business & our impact.
As Head of Finance, you will build and guide our Finance function - including but not limited to Accounting, FP&A, Treasury & Investor Relations.  You have a track record of building diverse teams of exceptionally talented people, with a focus on developing them to help them thrive in their careers.
You’re a high-level operator with the ability to manage complex projects seamlessly and effectively. You’re excited to be hands-on and embrace challenges to drive desired outcomes. 
This role would be called a Chief Financial Officer (CFO) in other companies, but at Outschool we have decided to take an unconventional approach to titling that aligns with our values and is focused on impact above status. You can read more about that here.


  • Develop and drive Outschool’s financial strategy, enabling the growth of our team, business & impact 
  • Prepare for and manage our IPO process by developing our capabilities to meet public company operating requirements
  • Contribute as a key member of Outschool’s executive team, partnering closely with other members of our team to ensure we’re working together in pursuit of our mission
  • Shape and tell our financial story to the world, effectively representing Outschool’s distinctive impact and approach to investors, analysts, and other strategic financing partners
  • Build & manage a world-class team and Finance function from an early stage, with a focus on FP&A, Investor Relations, and other teams that we do not currently have on staff
  • Develop our capabilities to meet public company reporting, compliance and regulatory requirements
  • Serve as a model for Outschool’s values, building on the cultural foundation that’s already in place as we continue to grow
  • Serve as a partner and advisor to our Board of Directors, providing updates on company finances and supporting board meetings 
  • Own our budgeting and forecasting processes in partnership with business operations and other stakeholders across the organization


  • A significant track record of leading strategic Finance teams - either as CFO or “#2” executive - ideally in a business that has grown from ~$100MM in revenue to $500MM+
  • Meaningful experience shaping and implementing financial strategies for public and/or private companies. 
  • An aptitude and motivation to frame finances in the context of mission and social impact
  • A desire to be hands-on in building our team and financial infrastructure from an early stage while always keeping an eye on the big picture
  • A track record of building diverse & thriving teams- you’re someone who knows how to identify and hire exceptional talent while creating an environment where people can grow and perform at a high level
  • An ability to think differently and the bravery to act on it. You push against the status quo because you see the gap between the opportunities of the future, emerging finance trends and current practices
  • A deep understanding of and credibility working with both private and public investors - you stay current with trends in financing markets (SPACs, direct listings, retail investments)
  • A data-centric mind with an ability to dive deep into the details of our business to make the right judgement calls


  • A plus if you have experience and understanding of large-scale online marketplaces or business
  • A plus if you’ve helped another company successfully prepare for an IPO
  • A plus if you have experience at companies with social impact or non-profit divisions
  • A plus if you have experience in both B2C and B2C companies


  • Shared Financial Success: Competitive salaries, stock options, and investment plans that make saving for retirement easier.
  • Health & Wellness: Comprehensive health, dental, vision, disability, and life insurance coverage options for employees and their families. Our medical benefits include fertility and family planning coverage. We also provide employees with online access to coaching and therapy sessions through our partner, ModernHealth. 
  • PTO & Family Benefits: PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends. 
  • Fully Distributed: With a team distributed across the US and Canada, we create a remote culture through expensable weekly meals, virtual events, expensable home office setup, and internet allowance.
  • Lifelong Learners: Annual budgets to self-direct our professional development as well as DEI learning. There’s also a budget for employees’ learners to take classes on Outschool! 
  • Community Impact: Outschool matches employee donations to established charities and has committed to donating $3M to Outschool.org non-profit programs.
Outschool is an equal opportunity employer. We view diversity as a moral imperative and competitive advantage. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We plan and structure our interviews to directly assess skills and experience. 
Outschool is committed to providing reasonable accommodations to disabled veterans and applicants with physical and mental disabilities. If you need assistance due to a disability, you may contact us at recruiting@outschool.com.
Must be a citizen or legal resident of the U.S. or Canada and reside in U.S. or Canada.
Job region(s): Worldwide/Anywhere
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