Director of Engineering, Reach

Riverside Insights

8d•Remote

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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.