General Counsel

As Riverside’s General Counsel, you will serve as a strategic legal advisor and guardian of compliance, helping the company navigate risk with integrity and foresight.  Supporting the Executive Leadership Team and reporting to the CFO, you’ll be a proactive business partner – delivering practical legal guidance that supports sound decisions across all areas of the organization. You’ll work cross-functionally to support measurable growth across the full customer journey—from awareness to advocacy. As a key internal advisor to teams such as HR, Finance, and Sales, you’ll add value through customer and vendor contracts, intellectual property protection, data privacy advising, and day-to-day corporate and employment matters. Success in this role requires navigating complex B2B & B2G environments with multiple products, channels, and stakeholders. Riverside operates in a regulated, government-funded education ecosystem—so experience in similar policy-influenced or compliance-intensive industries is essential. Your passion for education, innovation, and impact will fuel Riverside’s mission to empower educators, improve student performance, and build one of the world’s most impactful double bottom line businesses. In this role you will get to: 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. Disclaimer The above statements describe the general nature and level of the work performed by people assigned to this work. This list does not cover all possible duties, tasks, or responsibilities. Riverside Insights may amend or change responsibilities to meet the needs of the business and organization as necessary.  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. Physical Requirements This is a U.S.-based remote role, though we have shared co-working facilities in Chicago and Atlanta. May require some travel up to 10% at times. May require extended periods in a stationary position (sitting or standing). 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  Compensation: A reasonable estimate of the base compensation range for this position is $205,000 - $230,000 USD plus applicable bonus. This compensation range is specific to the United States and it incorporates many factors including but not limited to an applicant's skills and prior relevant experience and training; licensures, degrees, and certifications; internal pay ranges; and market data/range parameters. Who is Riverside Insights? Riverside Insights is a growth-focused business on a mission to elevate one billion lives globally by 2030 through research-based assessments and technology for educational professionals, students, clinical and behavioral health clients, and workforce talent.   Why Join Our Team?   At Riverside Insights, achieving real results for students and educators is more than talk – it's what we do. As we grow, so will you, offering the chance to expand your skills on an ambitious, solution-focused team. Join us in making great work possible, where your well-being and dedication to making an impact go hand in hand. If you're ready for an ambitious, collaborative environment, Riverside is the place for you.  Riverside Insights is an Equal-opportunity Employer:  Riverside Insights provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.  Our Commitment to Diversity & Inclusion:  At Riverside Insights, every employee has the right to a welcoming and inclusive workplace where their diverse backgrounds, experiences, and perspectives are valued and celebrated.  Thank you for considering joining our growing team and our mission to help elevate potential globally! Please check out www.riversideinsights.com to learn more about our work.