Head of Product



Canada · United States · Remote
Posted on Wednesday, May 8, 2024

The Company

Outschool’s mission is to inspire kids to love learning. In our fast-changing world, the traditional educational system struggles to meet the diverse and evolving needs of young learners. Outschool reimagines this system, offering flexible and engaging learning experiences as a supplement and alternative to traditional education. By connecting learners with a global community of teachers and peers through our online platform, we make learning personal, dynamic, and deeply human.

We've made significant strides since launching our marketplace of live online classes in 2017. Finding initial success with secular homeschoolers, we then expanded to enrichment learning to meet the needs of a wider audience, growing our business 16x since 2019. Post-pandemic, we have evolved our platform to power academic learning, incorporated AI, and have begun to grow our international community. We're proud to have served over 1M passionate learners with more than $100M in annual bookings.
Driving disruptive, positive change in education is rewarding and hard. Outschool team members are encouraged to challenge themselves, take risks, and grow in their careers. We look for talented people whose sense of urgency, innate curiosity, and determination to drive impact will help Outschool achieve outsized results in pursuit of our mission. We invite you to be part of an ambitious team dedicated to ensuring every learner can navigate the future with curiosity, resilience, and a love of learning.

Outschool has been named Fast Company’s most innovative EdTech company in the world, and one of the top ten best startups for women from Elpha. Outschool has also been one of BuiltIn’s Best Remote Places to Work for the last two years and has appeared on Y Combinator’s Top Companies list for the last three years.

About the Role

As the Head of Product at Outschool, you will use your experience building world-class products (ideally consumer, marketplace, or ed-tech) to uplevel Outschool’s product and customer value, during a phase of strategic expansion and transformation. This role would be called a Chief Product Officer in other companies and we are looking for candidates who bring CPO-level leadership experience - 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.

You will drive bold changes, significantly increase product velocity, and uplevel how our product organization operates. You will be tasked with expanding our product lines from a single to a multi-product strategy to satisfy more learning needs, drive growth, and expand our market opportunity.

You’ll never be bored. Education is a rewarding but complex domain. It will take all of your skill, experience, and potential to tackle one of the major societal challenges of our time, using our product, scale, resources, and market position as your levers.

Core Responsibilities:

  • Strategic Product Vision: Develop and implement transformative product strategies that increase customer value and simplify the user experience, moving beyond incremental updates.
  • Agility in Execution: Overhaul our product culture to prioritize quick decision-making and risk-taking, with an expectation of fast improvements to our pace and velocity post-onboarding.
  • Coach & Develop Product Management: Onboard and identify opportunities for development within the product team, building talent density and driving overall performance, with the goal of developing a world-class product org that continuously improves Outschool’s offerings.
  • Vision to Execution: Translate long-term visions into actionable plans, adeptly adjusting communication styles to different audiences to build alignment and drive execution.
  • Opinionated Leadership: Lead with a hands-on, assertive approach, making impactful decisions that may sometimes defy consensus to promote best practices and innovation.

Desired Experience & Skills:

  • Demonstrated leadership in scaling product teams within organizations of our size, ideally in consumer-focused sectors. Ed-tech or marketplaces is a plus but not required.
  • Proven ability to drive revenue growth through product initiatives, ideally with experience in an environment of at least $30M, with a preference for candidates who have guided growth from our current scale to significantly larger.
  • Strong record of fostering innovation and implementing significant changes that simplify user interactions and enhance product value.
  • Experience working closely with founders or in a startup environment, ideally translating visionary ideas into effective operational plans.
  • Skilled in attracting, inspiring, and coaching top-tier talent, building a collaborative and high-performing team.
  • Capable of making bold, strategic decisions and effectively communicating these choices, even when they involve tough trade-offs.
  • High level of ambition and a demonstrated impatience with delays or unmet promises; thrives in a dynamic, fast-paced environment.
  • Unafraid to challenge conventional thinking across all organizational levels to foster continuous improvement and innovation.

Outschool recruits across the US and Canada, and sets employee salaries to reflect local compensation and cost of living. For New York and California candidates, as well as candidates based in Seattle, WA the salary range for this role would be $325,000-$425,000 USD.

For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role would be $292,500-$382,500 USD.



We use Covey as part of our hiring and / or promotional process for jobs in NYC and certain features may qualify it as an AEDT. As part of the evaluation process we provide Covey with job requirements and candidate submitted applications. We began using Covey Scout for Inbound on March 21, 2024.

Please see the independent bias audit report covering our use of Covey here.


At Outschool, we believe that taking care of one another enables us to do our best work. To us that means:
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 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 support Outschool.org’s 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 neurodiverse individuals, applicants with physical and mental disabilities, and disabled veterans. For individuals who would like to request an accommodation, you may reach out to us at recruiting@outschool.com or through your Recruiting point of contact as you schedule your initial interview.
Benefits packages are included for full-time employees only.
Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada.
Once you submit your application, Outschool will process your personal data to evaluate your candidacy for employment. Unless specifically indicated otherwise, we hire employees only in the U.S. and Canada. Applicants else where should be aware that we may discard your application upon submission or we may ask if you would like us to retain it later should there be consideration (this is not typical at all). If you are selected for interviewing, your data will be shared with interviewers and personnel involved in that process. If not hired, your application will be retained for one year in case there is another suitable role. You may opt out of this at any time. Please see our Employee/Applicant Privacy Notice for more detailed information. If applicable, as you progress through the process, we will be clear about what information is being asked for and what happens with that information.