[Hiring] Director of Engineering @Riverside Insights

Role Description

Riverside Insights' Potential & Placement vertical has a clear north star: ensure every student with exceptional ability, outstanding potential, or unique learning needs is found as early as possible and given the opportunity to thrive. CogAT and Iowa Assessments are how school districts do that today. Together they're a nearly $50M business already serving 3 million students.

This role is a rare one: building an enterprise-grade platform from the ground up inside an organization with a trusted brand, established product-market fit, and millions of students already served. You're not proving the market exists, you're building the infrastructure that lets it grow.

You won't inherit existing architecture, tech debt, or a team. You'll build all three, on the path to an ambitious target: a 2028 launch and migrating our first million students onto this new platform. This is Director-level scope and ownership, and it's hands-on by design; you're writing code, in the architecture, shoulder to shoulder with your engineers every day. You'll define the technical vision, then build the fully dedicated technical team to execute it, drawing on Riverside's existing talent and new hires you bring in, all within your first 60 days. You'll work closely with your product, psychometrics, and content team members to bring our vision to life.

Make no mistake: this isn't a B2C mobile app. You're architecting a complex platform, with multiple interconnected components, real production volume, built for the workflows of schools and districts, at the security bar of a regulated data environment.

This is a small company mandate inside an established organization. That means a lean, scrappy, agile mindset, moving with real speed and without ego, in pursuit of an industry-changing vision that gets millions more kids found and given the support they need.

This role reports to the Chief Technology Officer.

Qualifications

• Has worked as a principal engineer or architect on large, complex, enterprise-grade production systems
• Has personally led a 0-to-1, B2B platform build as the senior technical owner
• Has built and led a team, combining existing and new hires, to hit an ambitious goal
• Has been the senior technical decision-maker on one project for at least 24 months
• Experience architecting and scaling production systems on AWS
• Experience operating in a regulated data environment (FERPA, COPPA, HIPAA, SOC 2, or similar)
• Full-stack fluency, front-end, back-end, architecture, DevOps, and testing
• Makes agentic coding tools and AI-assisted development the default way you build, not an add-on

Requirements

• Experience building assessment, test-delivery, or other high-stakes data platforms
• Experience building data or analytics/reporting platforms at scale
• Infrastructure-as-code experience (Terraform or equivalent)
• Experience integrating AI/ML capabilities into a production product
• Entrepreneurial background
• Comfortable presenting to and earning buy-in from senior leadership

Physical Requirements

• Remote
• Travel approximately 10 times a year for off-site team meetings
• May require stationary positions, sitting or standing, for extended periods

Benefits

• Medical, Dental, and Vision plans
• Company paid basic life and AD and D insurance
• Company paid long-term disability
• Paid Parental Leave
• 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
• 33 days of company paid time off (PTO, Holidays, Summer Fridays, Wellness Days)
• Weekly Focus Wednesdays
• Flexible work arrangements
• Tuition Reimbursement Program
• Company orientation and 30, 60, 90 Day Onboarding

Company Description

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.