Director of Engineering

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead the development of the Reach platform from inception to a pilot launch in Fall 2027, followed by the full launch of the next-generation CogAT assessment in 2028.

• Oversee the architecture, construction, and testing phases of the Reach platform.

• Design a sophisticated, multi-component platform scalable for B2B production volume, institutional buyers, and compliance with regulated data.

• Familiarize yourself with existing systems and the migration strategy, define the necessary team structure, and assemble a team of 6–10 engineers within 60 days utilizing current talent and new recruits.

• Manage the initial wave of customer migrations and enhance the day-one experience.

• Actively participate in coding alongside the engineering team.

• Make critical decisions regarding build-vs-buy-vs-partner for essential technical dependencies, adaptive engines, test delivery, and rostering.

• Set the benchmark for AI-native engineering practices at Riverside.

• Convert the Product team roadmap into a technical strategy, organizing architecture and infrastructure tasks while integrating AI into fundamental features such as the Reporting Engine.

• Collaborate across the organization through regular demonstrations of working software and provide transparent updates on progress, risks, and required decisions.

• Report directly to the Chief Technology Officer.

⛳️ Requirements

• Experience as a principal engineer or architect in large, intricate, enterprise-grade production systems.

• Proven track record of leading a 0-to-1 B2B platform build as the senior technical owner.

• Demonstrated ability to build and lead a team, integrating existing talent with new hires to achieve ambitious objectives.

• Held the role of senior technical decision-maker on a project for a minimum of 24 months.

• Proficient in architecting and scaling production systems on AWS.

• Experienced in working within a regulated data environment (FERPA, COPPA, HIPAA, SOC 2, or similar).

• Full-stack fluency encompassing front-end, back-end, architecture, DevOps, and testing skills.

• Utilizes agentic coding tools and AI-assisted development as standard practice rather than an additional feature.

• Background in building assessment, test delivery, or other high-stakes data platforms.

• Experience in constructing data or analytics/reporting platforms at scale.

• Familiarity with infrastructure-as-code practices (Terraform or similar).

• Experience in integrating AI/ML capabilities into production products.

• Entrepreneurial mindset.

• Comfortable presenting to and gaining buy-in from senior leadership.

• Remote position.

• Willingness to travel approximately 10 times per year for off-site team meetings.

🏝️ Benefits

• Medical, Dental, and Vision plans.

• Company-paid basic life and AD&D insurance.

• Company-paid long-term disability coverage.

• Paid Parental Leave.

• Options for supplemental life insurance.

• 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 employees and their dependents.

• 33 days of company-paid time off (PTO, Holidays, Summer Fridays, Wellness Days).

• Weekly Focus Wednesdays.

• Flexible work arrangements.

• Tuition Reimbursement Program.

• Comprehensive company orientation and 30, 60, 90 Day Onboarding.