General Counsel

Summary

Join Riverside Insights as the General Counsel, serving as a strategic legal advisor and ensuring compliance. You will report to the CFO and work with the executive leadership team, providing legal guidance across all organizational areas. Responsibilities include overseeing corporate legal matters, negotiating contracts, supporting M&A transactions, monitoring regulatory changes, and leading the legal team. Success requires experience in regulated, government-funded education, strong legal expertise, and exceptional communication skills. The role offers a remote-first work environment with benefits including medical, dental, vision, life insurance, retirement plan, paid time off, and flexible work arrangements. Riverside Insights is committed to empowering educators and improving student performance.

Requirements

• Juris Doctor (JD) from an accredited U.S. law school; licensed to practice law in Illinois or Georgia or eligible for in-house counsel registration
• Minimum 5 years of legal experience, including senior in-house counsel roles; experience in K–12 education, EdTech, or other mission-driven sectors preferred
• Strong background in commercial law, privacy, contracts, regulatory compliance, employment law, intellectual property, and corporate governance
• Experience operating within regulated, government-funded markets and navigating complex B2B/B2G environments with multi-product and multi-channel strategies
• Demonstrated ability to quickly understand consensus-driven, policy-influenced industries
• Exceptional communication skills and executive presence, with the ability to advise and influence senior leadership
• Strategic thinker with strong analytical skills and sound legal judgment under pressure
• Collaborative, proactive mindset with a bias toward continuous improvement and practical problem-solving
• Comfortable operating in a fast-paced, remote-first, cross-functional environment

Responsibilities

• Provide strategic legal counsel to the executive team and key departments (e.g., Product, Sales, HR, Finance), supporting business goals while managing risk
• Oversee all corporate legal matters, including contracts, compliance, intellectual property, employment law, and regulatory affairs
• Structure, draft, and negotiate a wide range of commercial agreements with customers, vendors, and partners
• Support M&A and strategic transactions in collaboration with external counsel, our Private Equity sponsor, and internal stakeholders – including due diligence, transaction execution, and post-close integration
• Monitor evolving legislation, regulatory changes, and policy shifts in the K–12 and EdTech markets; advise on implications and opportunities
• Build and lead a high-performing legal function grounded in agility, accountability, and operational excellence
• Manage internal legal team, external counsel relationships, and legal budgets to ensure cost-effective support and alignment with business priorities
• Support governance and compliance, including corporate policies, board communications, and internal training initiatives
• Act as a trusted advisor to the CFO and executive leadership team, fostering transparency and alignment on legal and risk-related matters

Benefits

• Medical, Dental, and Vision plans
• Company paid basic life and AD&D insurance
• Company paid short-term and long-term disability
• Supplemental life insurance options
• Company paid Employee Assistance Program (EAP)
• Retirement plan with discretionary company matching
• Flexible Spending Account (FSA) and Health Savings Account (HSA) options
• Premium subscription to Calm for employee and dependents
• Company paid time off (PTO)
• 13 named holidays, 2 floating holidays, and 4 early-release half days
• Quarterly Focus Days
• Flexible work arrangements
• Work-from-home expense reimbursement
• Tuition Reimbursement Program
• Company orientation and 30/60/90 Day Onboarding