Head of AI-First Engineering & Platform Scaling

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

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.