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Role Description

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.

Qualifications

• 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.

Benefits

• 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.