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About Step Up Tutoring

Step Up Tutoring is on a mission to drive student success by providing free online tutoring and mentorship for elementary and middle school students from under-resourced communities. Our unique value is in fostering the caring human relationship that forms between a student and their volunteer tutor during their 90 minutes of focused attention each week. We believe this connection is the key to unlocking learning gains, building confidence, and cultivating habits of success.

Since its founding in 2020 in partnership with Los Angeles Unified School District, Step Up has delivered over 250,000 hours of 1:1 tutoring to nearly 10,000 students, working across 25+ districts and with 40+ colleges and universities. We are pioneering AI-powered tutor assistance tools, working with Stanford University and Ai2/Allen Institute for AI. Step Up is backed by leading education funders including NewSchools Venture Fund, The Eli & Edythe Broad Foundation, Arrow Impact, Karsh Family Foundation and more.

The Opportunity

Step Up Tutoring is at a critical inflection point, and we are seeking a foundational engineering leader to own our technical strategy and execution. Your first and most critical responsibility will not be to simply execute a pre-determined plan, but to partner with the CEO, Product Leader and Board to make the single most important technical decision for our future: how we will migrate and rebuild our existing platform using a modern, AI-accelerated approach. We are not just looking for a leader to manage a rebuild; we are looking for a pioneer to design and implement a new way of building software at Step Up, leveraging AI as a force-multiplier to allow a small, scrappy team to achieve an outsized impact, so that we may unblock further innovative features for tutors, students and families.

You will not be working in a silo. You will be joining as a partner to our Head of Product. You own the "how"—the architecture, quality, and stability of our platform—while Product will own the "what" and the "why." Together, you will be jointly accountable for bringing our product vision to life. Over time, as the product and engineering organization grows, this role will become a core part of the broader product and engineering leadership team. We believe the most powerful products are born from the healthy, creative tension and collaboration between a brilliant engineering leader and a user-obsessed product leader. We are hiring for a partnership.

What You’ll Do

Lead Engineering Strategy & Execution

• Own engineering delivery across the core platform, internal tools, and integrations.
• Translate organizational priorities (session reliability, onboarding conversion, support efficiency, district needs, national growth) into a clear technical roadmap.
• Establish engineering operating cadence: sprint planning, prioritization, technical reviews, release management, incident response, and delivery reporting.

Pioneer an AI-Accelerated Engineering Culture

• Use AI to accelerate development across the lifecycle—from requirements translation to code scaffolding and testing.
• Deploy AI-powered tooling across the engineering workflow (code review, generative testing, CI/CD automation).
• Establish QA processes for AI-assisted development and user-facing AI features.
• Monitor, evaluate, and ensure quality, safety, and reliability of AI-generated outputs.

Lead Platform Rebuild & Data Migration

• Own delivery of the platform modernization and migration program (architecture, schema design, integrations, QA strategy, and rollout).
• Move business logic from fragile tooling into explicit, testable services.
• Coordinate engineers, contractors, and vendors with clear workstreams, milestones, and quality standards.
• Deliver modernization in stages aligned to the user journey (application → onboarding → matching → scheduling → session delivery → support).

Build Reliable, Scalable Systems

• Develop a platform that supports Step Up’s operational needs (matching, scheduling, messaging, attendance tracking, tutor support).
• Reduce maintenance burden through improved architecture and system design.
• Establish core engineering foundations: monitoring, audit logging, error tracking, CI/CD, environment management, and performance optimization.
• Ensure systems are built for national scale, configurable program requirements, and multi-language readiness.

Own Data, Privacy, Security & User Safety

• Serve as technical owner for data governance, privacy, security, and user safety across product and internal systems.
• Define data ownership, system-of-record decisions, and lifecycle practices (collection, access, retention, deletion).
• Implement privacy-by-design and least-privilege access controls.
• Lead security fundamentals: incident response, vulnerability management, credential practices, and vendor reviews.
• Build scalable safety infrastructure for a youth-serving platform (flagging, reporting, escalation workflows, and auditability).
• Ensure AI-enabled features meet privacy, safety, and evaluation standards.

Collaborate With Leadership

• Partner with the leadership team on strategy, prioritization, and technical tradeoffs. In particular, work closely with the Head of Product to translate product priorities into technical execution plans & delivery milestones.
• Align engineering capacity with session delivery goals and operational constraints.
• Improve cross-team coordination through clear planning artifacts, reporting, and risk management.

Lead Engineering Team

• Hire, manage, mentor, and develop team of full time and contract employee.
• Set standards for technical quality, testing, documentation, and maintainability.
• Build a culture of ownership, clarity, and mission-driven delivery.
• Evolve team structure over time to meet business needs and to support career growth of team members.

What Success Looks Like (First 6–18 Months)

• A clear modernization roadmap is consistently executed against, with predictable delivery and transparency on tradeoffs.
• Platform reliability improves materially (fewer incidents, faster resolution, better monitoring and alerting).
• A major data migration is completed (or meaningfully de-risked), with strong data integrity and trusted reporting/workflow states.
• Privacy, security, and user safety practices are strengthened and operationalized (clear ownership, access controls, auditability, incident readiness).
• Staff and volunteer-facing workflows become simpler and more reliable, reducing operational overhead and improving experience.
• Engineering, Product, and Program/Ops operate as a cohesive unit with shared priorities and strong day-to-day coordination.

Who You Are: The Ideal Candidate Profile

• Engineering Leader and Builder: 7+ years of software engineering experience. You can split your time between leading strategy and getting into the details and contributing to hands-on engineering deliverables.
• A Pragmatic Systems Builder: You have experience in both large, well-resourced environments and scrappy, lean startups. You know what "great" looks like, but more importantly, you know how to apply those principles pragmatically to a small team. You find creative ways to achieve 80% of the value with 20% of the effort and understand that building for the future doesn't mean over-engineering for the present.
• An AI-Native Engineering Leader: You see AI not just as a product feature, but as a fundamental tool to transform the engineering process itself. You have proven, hands-on experience:

• Implementing AI-powered development tools (e.g., for code generation, automated testing, CI/CD) to increase team productivity.
• Building and shipping AI-first systems in a production environment.
• Thinking deeply about how to QA, monitor, and ensure the reliability of AI/ML systems and their outputs.

• Program driver: You’ve led complex cross-functional technical programs (platform rebuilds, migrations, integrations) with high operational stakes.
• Systems + Reliability Mindset: You balance speed with quality, build testable systems, and introduce pragmatic operational discipline (monitoring, incident management, release hygiene).
• Data/Privacy/Security Ownership: You’ve owned or meaningfully contributed to privacy/security practices and can right-size controls for a lean organization serving youth and operating in district partnership contexts. Experience shipping AI/ML-enabled features responsibly (privacy, safety, evaluation, monitoring) is required.
• Execution + Clarity: You communicate simply, manage priorities, and create structure without bureaucracy. You’re comfortable making decisions with imperfect information.
• Strong Collaborator: You partner effectively with product/program/ops leaders and translate between user needs, operational constraints, and engineering reality.
• Mission-Driven: You’re motivated by educational equity and care deeply that technology supports (and never erodes) the human relationship at the center of tutoring. Experience in ed-tech is highly desirable.

Why You’ll Love Working at Step Up Tutoring

• Foundational impact: This isn’t just an optimization role—you’ll help build the new technical backbone for national scale.
• Influence and leadership: Work directly with the senior leaders to shape strategy and execution.
• Collaboration with leading education organizations: Collaborate with organizations working on the forefront of application of AI to improve education, including Stanford Accelerator for Learning, Ai2/Allen Institute for AI, NewSchools Venture Fund, and LeanLab Education, as well as some of the largest school districts in the country including Los Angeles Unified and 40+ others.
• Critical mission: You will go to work every day knowing your efforts are directly creating educational opportunities and driving impact for students in need.
• Passionate & experienced team: Join a dedicated group of staff, Board members, and volunteers who are all committed to the mission. Team members have experience in leading EdTech organizations, including Khan Academy and Kyron Learning.

Salary & Benefits

• Compensation: $150,000-$190,000 plus opportunity for performance-based bonus
• Benefits for Full-Time Employees: Comprehensive health, dental, and vision coverage (company covers 80% of base plan for individuals, 50% for dependents); 401k retirement plan, Flexible PTO; Professional Development; work-from-home stipend.