VP of Engineering

Screencastify; Chicago (IL); On-site; USD 180,000 - 220,000; Full time

Benefits offered by this job

401(k) match

Annual Performance Bonus

Flexible Time Off

Parental Leave

Medical, Dental, & Vision Insurance

Divvy Bike Membership

Job summary

Castify, based in Chicago, is seeking a VP of Engineering to lead and scale its engineering organization across multiple product areas. This executive will partner with Product and GTM to define the technical vision, drive architectural excellence, and govern AI-powered platforms used by millions.

The role requires 12+ years of leadership experience in SaaS, a hands-on approach, and strong communication across all levels, with a focus on delivery and reliability.

Qualifications

• 12+ years of software engineering leadership in high-growth SaaS or product-led tech companies.
• Experience in early-stage or growth-stage startups with ownership mindset.
• Hands-on leader comfortable with architecture and code-level discussions.
• Fluent in AI-driven software engineering practices and tooling.
• Strong foundation in modern web tech, cloud infrastructure, distributed systems, and scalable architectures.

Responsibilities

• Lead a high-performing Engineering organization across multiple product areas.
• Champion AI-powered tools and workflows to accelerate velocity and quality.
• Partner with Product to define technical strategy, roadmaps, and execution.
• Establish scalable systems, development standards, and operational best practices.
• Oversee architecture, development, testing, deployment, and reliability of products.
• Shape our AI-first product strategy with experimentation and scalable implementation.
• Guide technical decisions across frontend, backend, infrastructure, data, and platform initiatives.
• Remove blockers and align engineering efforts to business outcomes.
• Foster ownership, accountability, and continuous improvement in the engineering culture.

Skills

Leadership

Hands-on engineering

AI tooling adoption

System design

Communication

Cloud infrastructure

Web technologies

Architectural decisions

Tools

TypeScript

React

Node.js

GCP

Job 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

What started as the simplest and most reliable screen recorder in the world, with millions of users, is now a multi-product, AI-first platform. Our near future is full of ambitious new goals, features, and products that will enable us to further improve how we provide service to our users and accelerate growth.

We prioritize fast iteration without compromising quality while maintaining attention to detail that creates the kind of seamless, high-quality experiences we’re known for. We’re looking for an experienced, strategic VP of Engineering to lead and scale our engineering organization as we continue building innovative products that impact millions of users worldwide.

This role will partner with Product and GTM teams to define and execute our technical vision, strengthen engineering operations, and help shape the future of video communication and AI-powered learning experiences.

What you’ll do:

• Lead a high-performing Engineering organization across multiple product areas and platforms.
• Champion the adoption of AI-powered engineering tools and workflows to accelerate team velocity and output quality.
• Partner with Product leadership to define technical strategy, roadmap priorities, and execution plans.
• Drive engineering excellence by establishing scalable systems, development standards, and operational best practices.
• Oversee the architecture, development, testing, deployment, and reliability of our products and infrastructure.
• Shape and evolve 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.
• 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.

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, comfortable diving into architecture and code‑level discussions to guide decisions and solve technical problems.
• Are fluent in how AI is changing the software engineering craft — you've personally used AI coding tools and have driven adoption of AI‑assisted workflows across a team
• Have a strong foundation across modern web technologies, cloud infrastructure, distributed systems, and scalable architectures, with experience in end-to-end systems (frontend, backend, platform, infrastructure, and DevOps) using tools like 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 across all levels from engineers to executives balancing technical depth with clear, outcome‑oriented storytelling.
• Excel in ambiguity, moving quickly and decisively without sacrificing engineering quality.

This is a Chicago‑based position 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.

• 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.