[Hiring] Vice President, Engineering @The Princeton Review

Role Description

The VP of Engineering is a senior leadership role with broad scope across engineering, QA, and data, with deep involvement in infrastructure and security strategy. Reporting to the Chief Product & Technology Officer, this leader will own the strategy, execution, and organizational health of the full technical organization.

This is a transformation role. In alignment with ambitious company goals for growth and sustained execution excellence, we are investing in a step-change in how we build and ship product:

• Embedding AI-native workflows into how we build.
• Moving toward small, highly leveraged teams that conceive and ship in tight cycles.

The VP of Engineering will own that shift — building the engineering culture, practices, and org design that maximize developer productivity and get great product into users' hands faster.

This is a role for a leader who is comfortable operating at a high altitude — setting direction, communicating clearly to executive and board audiences, and making sound investment decisions — while remaining close enough to the work to develop leaders, drive accountability, and earn credibility with the team.

Qualifications

• 15+ years in software engineering, with significant time in senior engineering leadership (director level and above).
• Experience leading organizations that span multiple functions — product engineering, QA, data, and infrastructure.
• A track record of shipping product, not just managing roadmaps — you know what great execution looks like and how to build the conditions for it.
• Deep experience building AI-powered products, leading teams that do, and embedding AI tooling into engineering workflows.
• Fluency in agile and product engineering principles, and the ability to coach and model them across an organization.
• Strong executive communication skills; comfortable presenting roadmaps, tradeoffs, and risk narratives to senior leadership and boards.
• Strong people instincts — you develop leaders, hold the bar on performance and culture, and know how to manage effectively through existing leaders and teams.
• A natural collaborator who builds trust across functions and levels — you get things done through relationships, not just authority, and you make the people and teams around you better.
• Comfortable operating in a mid-sized company where leaders are close to the work and expected to lead from the front.

Requirements

• Set and maintain high standards for delivery velocity, quality, and predictability across all engineering teams.
• Evolve the processes, practices, and accountability systems that enable consistent execution at scale, including CI/CD adoption and a shift-left approach to quality ownership.
• Drive the organization’s shift toward modern, cross-functional product teams; partner closely with product leadership to build iterative, collaborative ways of working with rapid feedback loops.
• Own the 6–24 month technology roadmap: define where we want to be, make the tradeoffs explicit, and work backwards to a credible plan.
• Provide architectural vision and oversight across the organization; ensure engineering investments align with long-term business goals.
• Partner closely on infrastructure and security strategy, ensuring the long-term sustainability and resilience of our systems.
• Make ongoing sound investment decisions around technical debt, platform modernization, and operational resilience.
• Lead development of AI-powered products in partnership with product and data teams.
• Provide strategic oversight and direction for the data team — helping the team set the vision for the data platform and capabilities the product and AI agenda require.
• Assess, develop, and grow the engineering organization; build the management layer and career paths that will scale the team through the next phase.
• Serve as a core member of the technology leadership team, contributing to the strategic direction of the overall technology organization.
• Build strong working relationships with product, content, and business stakeholders.

Benefits

• Competitive salary which commensurates with experience and skills.
• US Pay Range: $220,000 - $250,000 USD.