VP of Engineering

Screencastify•Chicago, IL

1d•Hybrid

About The Position

Castify is seeking a hands-on VP of Engineering to join its leadership team as the company evolves Screencastify from a widely used screen recorder into an AI-first learning and collaboration platform. The VP will lead a small, high-performing engineering team, set technical direction, drive AI initiatives, and partner closely with Product to support expansion into new markets and product-led growth. The role combines strategic leadership with direct technical involvement in a fast-moving startup environment. The position is based out of Screencastify’s Fulton Market office in Chicago and follows a hybrid schedule with three days a week in the office. The expected annual base salary starts at $200,000, with an annual performance bonus opportunity. Final compensation may vary based on experience and qualifications.

Requirements

12+ years of software engineering experience leading teams in high-growth SaaS or product-led technology companies.
Experience working in early-stage or growth-stage startups with fewer than 50 people, and ability to thrive with ownership and an entrepreneurial mindset.
Hands-on technical leadership, including the ability to engage in architecture and code-level discussions.
Firsthand experience with AI coding tools and driving adoption of AI-assisted engineering workflows.
Strong technical foundation in distributed systems, scalable architectures, and end-to-end systems across frontend, backend, platform, infrastructure, and DevOps.
Proficiency in modern web technologies and cloud infrastructure, including TypeScript, React, Node.js, and GCP.
Track record of building and scaling products used by millions of users, with expertise in system design, reliability, scalability, and security.
Ability to translate company strategy into clear technical direction and drive execution in a fast-moving, high-accountability environment.
Effective communication with engineers and executives, balancing technical depth with clear, outcome-oriented messaging.
Ability to thrive in ambiguity and move quickly and decisively without sacrificing engineering quality.

Responsibilities

Lead a small, high-performing Engineering team across multiple product areas and platforms.
Set technical direction and partner with Product leadership to define roadmaps, prioritize initiatives, and deliver business goals.
Champion AI-powered engineering tools and workflows to accelerate team velocity and output quality.
Shape the 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 product and infrastructure architecture, development, testing, deployment, and reliability.
Drive engineering excellence through scalable systems, development standards, and operational best practices.
Remove blockers, clarify priorities, and align engineering efforts with business outcomes.
Foster an engineering culture grounded in ownership, accountability, and continuous improvement.