# VP of Engineering > Screencastify · Chicago, United States (Hybrid) · Full-time · Posted 2026-11-04 **Workplace:** hybrid **Department:** Engineering ## Description ### 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 ownership end-to-end. We love a challenge, a good problem, and teammates who bring both creativity and follow-through. Rule #1: Be a good person. **Compensation** The expected annual base salary for this role is anticipated to start at $200,000 with an annual performance bonus. Final compensation may vary based on experience and qualifications. ## Benefits - **Competitive Compensation.** We take a data-driven approach to our compensation strategy so all employees are paid competitively and fairly. - **401(k) & Annual Performance Bonus Opportunity.** We want to invest in present you and future you, which is why we offer a 401(k) match + Annual Performance Bonus opportunity. - **Flexible Time Off (FTO) Policy.** We recognize that time off to rest and recharge is important. The Flexible Time Off Policy (FTO) is designed for our employees to do just that -- balance work and life while maintaining well-being. - **Parental Leave.** Generous paid time off for parents to bond with the newest addition to their family! - **Medical, Dental, & Vision Insurance.** We offer comprehensive health benefits, including medical, dental, and vision insurance. Plus, all employees receive a free One Medical membership. - **Divvy Bike Membership.** If you’re in Chicago, take advantage of an annual Divvy membership -- on us. At Castify, we foster an inclusive, supportive, fun, and challenging team environment. We value having a team that is made up of a diverse set of backgrounds and respect the healthy expression of diverse opinions. We embrace experimentation and the examination of all kinds of ideas through reasoning and testing. Come join us as we continue to change the world through video. Castify is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender, sexual orientation, national origin, age, genetic information, gender identity, disability, Veteran status or any other characteristic protected by federal, state or local law. ## Apply [Apply at Screencastify](https://apply.workable.com/screencastify/j/35A8686204/apply) --- Powered by [Workable](https://www.workable.com)