VP of Engineering

Screencastify • Chicago, IL

2d • Hybrid

About The Position

Castify (Creators of Screencastify) is a leading technology company dedicated to improving communication and learning outcomes with video. We have established ourselves as a leader in the K-12 education sector in the United States and we are critical in helping scale a teacher and improve student outcomes. We are also actively expanding into new and exciting markets outside of K-12 including bringing our tested solution into companies and organizations. Castify is used by over 15M people today and is seeking a VP of Engineering to join our Squad!

What started as the simplest and most reliable screen recorder in the world, with millions of users, is now a multi-product, AI-first platform. Our near future is full of ambitious new goals, features, and products that will enable us to further improve how we provide service to our users and accelerate growth.

We prioritize fast iteration without compromising quality while maintaining attention to detail that creates the kind of seamless, high-quality experiences we’re known for. We’re looking for an experienced, strategic VP of Engineering to lead and scale our engineering organization as we continue building innovative products that impact millions of users worldwide.

This role will partner with Product and GTM teams to define and execute our technical vision, strengthen engineering operations, and help shape the future of video communication and AI-powered learning experiences.

Requirements

• 12+ years of software engineering experience leading teams in high-growth SaaS or product-led technology companies.
• Worked in early-stage or growth-stage startups (fewer than 50 people) and thrive in environments that require ownership and an entrepreneurial mindset.
• Hands-on technical leader who stays close to the work, comfortable diving into architecture and code-level discussions to guide decisions and solve technical problems.
• Fluent in how AI is changing the software engineering craft — personally used AI coding tools and driven adoption of AI-assisted workflows across a team.
• Strong foundation across modern web technologies, cloud infrastructure, distributed systems, and scalable architectures, with experience in end-to-end systems (frontend, backend, platform, infrastructure, and DevOps) using tools like TypeScript, React, Node.js, and GCP.
• Track record of building and scaling products used by millions of users, with deep expertise in system design, reliability, scalability, and security.
• Can translate company strategy into clear technical direction and drive strong execution in a fast-moving, high-accountability environment.
• Communicate effectively across all levels from engineers to executives balancing technical depth with clear, outcome-oriented storytelling.
• Excel in ambiguity, moving quickly and decisively without sacrificing engineering quality.

Responsibilities

• Lead a high-performing Engineering organization across multiple product areas and platforms.
• Champion the adoption of AI-powered engineering tools and workflows to accelerate team velocity and output quality.
• Partner with Product leadership to define technical strategy, roadmap priorities, and execution plans.
• Drive engineering excellence by establishing scalable systems, development standards, and operational best practices.
• Oversee the architecture, development, testing, deployment, and reliability of our products and infrastructure.
• Shape and evolve our AI-first product strategy by enabling experimentation, rapid iteration, and scalable implementation.
• Guide technical decision-making across frontend, backend, infrastructure, data, and platform initiatives.
• Ensure strong execution across teams by removing blockers, clarifying priorities, and aligning engineering efforts to business outcomes.
• Foster a strong engineering culture grounded in ownership, accountability, and continuous improvement.

Benefits

• Annual performance bonus
• 401(k) match
• Flexible Time Off (FTO) Policy
• Generous paid time off for parents to bond with the newest addition to their family
• Comprehensive health benefits, including medical, dental, and vision insurance
• Free One Medical membership
• Annual Divvy membership

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed