VP of Engineering

Screencastify

Location: Chicago, Illinois, United States · published
Type: Full-time
Department: Engineering
Seniority: VP
Source: Workable

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.

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.