VP of Engineering

Screencastify•Chicago, IL

1d•Hybrid

About The Position

Castify, the creators of Screencastify, is seeking a hands-on VP of Engineering to join its leadership team as the company evolves from a widely used screen recorder into an AI-first learning and collaboration platform. The VP of Engineering will lead a small, high-performing team, set technical direction, drive AI initiatives, and partner closely with Product to support expansion into new markets and product-led growth. The role calls for an experienced SaaS engineering leader who combines strategic thinking with hands-on technical leadership and can use a lean team and AI to drive business growth. This position is based at Screencastify’s Fulton Market office in Chicago and follows a hybrid schedule with three days per week in the office.

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 an ownership-oriented, 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 across distributed systems, scalable architectures, and end-to-end systems, including frontend, backend, platform, infrastructure, and DevOps.
Proficiency in modern web technologies and cloud infrastructure, including TypeScript, React, Node.js, and GCP.
A 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 increase team velocity and output quality.
Shape the AI-first product strategy by enabling experimentation, rapid iteration, and scalable implementation.
Guide technical decisions 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 work with business outcomes.
Foster an engineering culture grounded in ownership, accountability, and continuous improvement.