Director of Engineering

THE OPPORTUNITY

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 a nearly $50M business already serving 3 million students.

This is a hands-on, principal-level technical role. You're the senior technical owner, not managing a team through someone else's architecture: writing code, in the architecture, shoulder to shoulder with your engineers every day.

The opportunity itself is rare: build 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 platform architecture and data model that let it grow, at the security bar of a regulated data environment (FERPA, COPPA, and similar), while making the build-vs-buy-vs-partner calls on core components like the adaptive engine, test delivery, and rostering.

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. Once you're deep on the existing systems and the migration plan, you'll define and build the fully dedicated technical team to execute it, drawing on Riverside's existing talent and new hires you bring in, within your first 60 days. You'll work closely with product, psychometrics, and content throughout.

Make no mistake: this isn't a B2C mobile app. You're architecting a complex, multi-component platform, built for real production volume and the workflows of schools and districts.

This is a small company mandate inside an established organization: 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.

What You'll Do

• Lead the 0-to-1 build. Own architecture, construction, and testing of the Reach platform through a Fall 2027 pilot, and the next-generation CogAT assessment through full 2028 launch.
• Architect for B2B scale. Design a complex, multi-component platform built for real production volume and institutional buyers, meeting the compliance bar of a regulated data environment.
• Build your team, within 60 days. Get deep on existing systems and the migration plan, then define the team you need and build it, drawing on existing talent and new hires within a 6-10 engineer budget.
• Own the first migration wave. Ensure the initial cohort of customers moving onto the new platform gets a day-one experience that's better than what they had, not just a like-for-like switch.
• Stay hands-on. Actively coding alongside your team, not reviewing architecture diagrams from a distance.
• Own build-vs-buy-vs-partner calls on core technical dependencies, adaptive engine, test delivery, rostering, with clear, cost- and risk-informed recommendations.
• Set the standard for AI-native engineering at Riverside, ways of working that let a small team move like a much bigger one.
• Own technical roadmap execution. Translate the Product team’s roadmap into a technical plan, sequencing architecture and infrastructure work, including where and how AI gets built into core capabilities like the Reporting Engine.
• Partner across the business. Regular demos of working software, transparent updates on progress, risk, and decisions needed.

Requirements

Must-Have 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

What You'll Bring

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

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.

WHY JOIN OUR TEAM?

At Riverside Insights, achieving real results for students and educators is more than talk, it is 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 are ready for an ambitious, collaborative environment, Riverside is the place for you.

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

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.

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