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.

The Role

Outschool is looking for a strategic, impact-seeking Lead Counsel, Product & Commercial to join our Legal team. This is a highly visible role for a business-minded lawyer who thrives at the intersection of product development, commercialization, and regulatory risk.

You will serve as the primary legal partner to Product teams, supporting all stages of product development, launches, and monetization, while also leading Outschool’s commercial legal function. You’ll be a trusted advisor to cross-functional leaders, known for delivering practical, creative, and timely guidance that enables the business to move forward thoughtfully and compliantly.

You are a jack-of-all-trades who thrives in a dynamic environment, balancing multiple high-impact initiatives with strong execution, sound judgment, and timely delivery. While titled “Lead Counsel” at Outschool, this role is equivalent in scope and responsibility to a Director-level role at many companies. You are energized by complexity, enjoy being hands-on, and are excited to help scale a mission-driven, kid-focused platform.

Core Responsibilities:

Product & Regulatory Counsel

Serve as the primary legal advisor to Product, Engineering, Marketing, Trust & Safety, and Operations teams, partnering across the product lifecycle to embed legal and compliance considerations into product decision-making.
Spot and analyze legal issues across consumer protection, privacy and data protection, employment and independent contractor considerations, trust & safety, litigation risk, and other regulatory requirements.
Review global products, features, platforms, and initiatives to provide practical, risk-based guidance across multiple jurisdictions.
Advise senior leadership on complex, high-impact matters and drive cross-functional alignment on strategic initiatives.
Ability to work across the organization and with all levels of different internal stakeholders.

Commercial & Operational Legal Leadership

Lead Outschool’s commercial legal work, including reviewing and negotiating vendor agreements, advising on legal terms for marketing and growth initiatives, and managing outside counsel.
Develop and maintain scalable templates, playbooks, and processes to support operational efficiency.
Knowledge and ability to assist with other legal projects on an as-needed basis.

Desired Experience & Skills:

7+ years of combined law firm and in-house experience (including at least 4 years in-house), with significant responsibility advising on product and commercial matters.
Active membership in at least one U.S. state bar (or eligibility to register as authorized in-house counsel).
Proven ability to distill complex legal issues into clear, actionable guidance that business partners can operationalize.
Strong analytical skills and sound commercial judgment, with the ability to balance legal risk and business objectives, and exercise impeccable judgment in identifying when to escalate issues or engage internal stakeholders and outside counsel.
Excellent communication, writing, and influence skills, with experience working cross-functionally and leading complex matters end-to-end.
SF or NYC candidates preferred for hybrid work, with flexibility for remote

Other Considerations:

Experience advising on both B2C and B2B products.
Background in high-growth technology companies, marketplaces, or platforms, including familiarity with independent contractor or gig-economy issues.
Experience with kid-focused or education-related consumer products and COPPA.
Interest in or experience advising on generative AI or other emerging technologies.

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 $260,000 - $300,000 USD.

For Washington candidates outside of Seattle, as well as Colorado candidates, the salary range for this role would be $234,000 - $270,000 USD.

#LI-Remote

Benefits & Culture:

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, retirement plans.
Health & Wellness: Comprehensive medical, dental, vision, disability, and life insurance — plus fertility/family planning coverage and access to ModernHealth coaching & therapy.
PTO & Family Benefits: Generous PTO and family leave policies.
Hybrid & Remote-Friendly: Outschool has a distributed team across the U.S. and Canada and a new office in San Francisco. Bay Area–based employees work in the office part of the week and receive commute-related benefits. Team members outside the Bay Area remain fully remote, with support for expensable home office setup, internet, and weekly meals to stay connected no matter where you are.
Lifelong Learners: Annual budgets for professional development and DEI learning; budgets for children to take Outschool classes.
Community Impact: Outschool matches employee donations to eligible charities and supports Outschool.org’s nonprofit 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.

If you require a reasonable accommodation to participate in the job application or interview process, please contact [email protected].

Benefits packages are included for full-time employees only. Please note benefits and perks may vary for employees based outside of the US and Canada.

Full-time employees must be a citizen or legal residents of the U.S. or Canada and reside in U.S. or Canada, unless specifically indicated otherwise.

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.

Lead Counsel, Product & Commercial

TLDR

The Company:

Benefits & Culture:

Benefits