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Director of Engineering

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At Insomnia Cookies, we believe warm cookies and tech go hand in hand. As we continue to expand our late-night empire, our digital platforms are key to delivering exceptional guest experiences—from craveable online ordering to smooth in-store systems. We're seeking a Director of Engineering to lead the talented team behind our web and mobile applications and scale our architecture for the next chapter of growth.

The Director of Engineering is a hands-on leader who will shape the future of Insomnia’s digital experience. You’ll lead the engineering teams behind our ecommerce, loyalty, and store technologies, setting a high bar for both team performance and technical quality. You’ll operate as a force multiplier—removing roadblocks, coaching talent, guiding architectural decisions, and pushing the boundaries of modern engineering practices, including AI-augmented development.

Reporting to the VP of Digital Product & Development, the Director will manage a team of three Full Stack Engineering Leads, and indirectly oversee engineers across multiple scrum teams. This is a hands-on leadership role where technical excellence, people development, and executional clarity are key. You’ll help set and uphold best practices, modern development standards, and ensure delivery of high-quality, scalable, and secure software.

Sweet Position Perks:

• 4 day work week!! (yupp, we get every Friday off)

• A competitive base salary plus annual bonus compensation package

• A relocation package to assist in moving to the Greater Philadelphia area

• Eligibility for our Long-Term Incentive Program

• Excellent comprehensive benefits coverage that includes medical, dental, vision & pet insurance plans

• 401K with contribution match

• 3 weeks paid vacation plus 2 paid Insomnia personal wellness days

• Relaxed, fun, come as you are office culture

• Free cookies, branded swag and so much more!

Job Responsibilities:

Leadership & Team Management

•Lead, coach, and grow a team of engineering leads and their direct reports, creating an environment of accountability, collaboration, and continuous learning

•Cultivate an engineering culture focused on innovation, speed, and quality—balancing long-term architecture with near-term delivery

•Own the technical rhythm of the team: rituals, code quality, reviews, standups, and release cadence

•Encourage experimentation and exploration of emerging technologies, including AI tooling, to improve developer velocity and product performance

•Establish and maintain engineering best practices, code quality standards, and architectural consistency across teams

•Partner with the VP of Digital Product & Development to ensure seamless execution of the product roadmap and sprint planning

•Champion agile methodologies, promote cross-functional collaboration, and streamline development operations

Engineering Oversight

•Lead development across the full stack (ReactJS, PHP/Laravel, MySQL) with deep involvement in architecture, performance optimization, and scaling

•Evaluate and implement modern tooling, patterns, and frameworks to keep our platform cutting-edge, including cloud infrastructure improvements, system integrations, and CI/CD enhancements

•Drive adoption of developer productivity tools and testing automation to reduce friction and improve release confidence

•Oversee code reviews, release cycles, testing coverage, and post-release monitoring to uphold high quality and reliability

Strategic Planning & Execution

•Contribute to the technology strategy and participate in long-term planning with product, design, and data teams

•Identify areas for innovation and optimization across frontend, backend, APIs, and infrastructure

•Actively collaborate on platform modernization and refactoring initiatives that improve performance and reduce technical debt

•Stay ahead of trends in software engineering and propose new methods to boost reliability, speed, and team effectiveness

Mentorship & Culture

•Build a healthy engineering culture grounded in transparency, innovation, and ownership

•Provide career development support and mentorship to engineers and leads

•Champion inclusivity and diversity within the engineering team

Tech Stack You’ll Be Working With:

Frontend: ReactJS, HTML5, CSS, JavaScript
Backend: PHP/Laravel, RESTful APIs, GraphQL (plus!)
Database: MySQL (bonus if experience with Postgres)
Tooling: Git, CI/CD pipelines, Agile project management tools (JIRA, Azure Boards, etc.)
Testing: Unit and integration testing frameworks
Other: ORM frameworks (Eloquent, Django, Active Record), experience with cloud infrastructure and DevOps pipelines preferred
Open to exploring new stacks and tools where they provide meaningful business or developer productivity gains

Desired Skills & Qualifications:

7+ years in full-stack development with increasing levels of responsibility; 2+ years in people leadership, ideally in fast-paced or high-growth environments
Comfortable rolling up your sleeves while mentoring others and setting standards for technical excellence
Strong proficiency in full-stack web development, especially with ReactJS and PHP/Laravel
Proven experience managing, mentoring, and scaling engineering teams
Deep understanding of modern engineering principles, including object-oriented programming, testing strategies, and agile development
Familiarity with tools or approaches that enhance developer efficiency—whether through AI copilots, DevOps automation, or architectural simplification
Excellent communication skills and ability to translate technical concepts for non-technical stakeholders
Track record of launching and scaling digital products, especially in ecommerce or omnichannel consumer brands
Bachelor's degree in Computer Science, Engineering, or a related technical field (or equivalent work experience)

Insomnia Cookies Glassdoor Company Review

3.2

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CEO of Insomnia Cookies

Seth Berkowitz

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What You Should Know About Director of Engineering, Insomnia Cookies

At Insomnia Cookies, we believe that there's nothing better than combining warm, delicious cookies with cutting-edge technology. As we continue to expand our late-night cookie empire, we're on the lookout for a passionate and talented Director of Engineering to join our team in Center City, Philadelphia. In this dynamic role, you'll lead our engineering team responsible for web and mobile applications that enhance the guest experience—from seamless online ordering to efficient in-store systems. As a hands-on leader, you'll take charge of guiding our engineering initiatives across various projects, including e-commerce and loyalty platforms. You'll set high standards for team performance and technical quality, while eliminating roadblocks and fostering a culture of continuous learning and innovation. Working closely with the VP of Digital Product & Development, you'll play a pivotal role in shaping our technical strategy and ensuring that we uphold best practices in software development. With perks like a four-day work week, competitive salary, relocation assistance, and a fun, relaxed workplace culture, this is not just another job—it's an opportunity to be part of something extraordinary. Join us, and let's create the future of digital experiences in the cookie world together!

Frequently Asked Questions (FAQs) for Director of Engineering Role at Insomnia Cookies

What are the key responsibilities of a Director of Engineering at Insomnia Cookies?

The Director of Engineering at Insomnia Cookies is responsible for leading a team of engineering leads, overseeing the development of web and mobile applications, and ensuring best practices in software development. You'll manage project timelines, guide architectural decisions, and foster a culture of innovation, collaboration, and high performance.