Well, hello there 👋
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!
About this role
We are evolving from a widely-used screen recorder into an AI-first learning and collaboration platform, and we’re looking for a hands-on VP of Engineering to join our leadership team and help shape what’s next. As we expand into new markets and invest in product-led growth, you'll lead a small high-performing engineering team, set technical direction, drive AI initiatives, and partner closely with Product to deliver our vision. This is an opportunity for an experienced SaaS engineering leader who thrives in a fast-moving startup environment, combines strategic thinking with hands-on technical leadership, and knows how to leverage a lean team and AI to drive business growth.
What you'll do:
Lead a small high-performing Engineering team across multiple product areas and platforms.
Set technical direction and partner closely with Product leadership to define roadmaps, prioritize initiatives, and deliver on business goals.
Champion AI-powered engineering tools and workflows to accelerate team velocity and output quality.
Shape 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.
Oversee the architecture, development, testing, deployment, and reliability of our products and infrastructure.
Drive engineering excellence through scalable systems, development standards, and operational best practices.
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.
Requirements
You're perfect for this role if you:
Bring 12+ years of software engineering experience leading teams in high-growth SaaS or product-led technology companies.
Have worked in early-stage or growth-stage startups (fewer than 50 people) and thrive in environments that require ownership and an entrepreneurial mindset.
Are a hands-on technical leader who stays close to the work and can dive into architecture and code level discussions to guide decisions.
Bring firsthand experience with AI coding tools and have driven adoption of AI-assisted engineering workflows.
Have a strong technical foundation across distributed systems, scalable architectures, and end-to-end systems (frontend, backend, platform, infrastructure, and DevOps).
Are proficient in modern web technologies and cloud infrastructure, including TypeScript, React, Node.js, and GCP.
Possess a 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 with engineers and executives, balancing technical depth with clear, outcome-oriented messaging.
Thrive in ambiguity, moving quickly and decisively without sacrificing engineering quality.
This role is based out of Screencastify’s Fulton Market office in Chicago and follows a hybrid schedule with 3 days a week in the office.
Working at Castify
We are results-focused, fast-moving, and here to change how the world communicates and learns through video. We value accountability, speed, and people who take…