Digital Product & Development

At Insomnia Cookies, our mission is to fuel life's moments with warm, delicious cookies delivered straight to your door—late-night and beyond. Behind every sweet experience is a powerhouse tech team redefining the boundaries of digital convenience, indulgence, and joy. We're now looking for a Vice President of Digital Product & Development to lead our next evolution in ecommerce and in-store technology, driving a best-in-class customer experience and scaling our internal systems to support a rapidly growing brand.

As the VP of Digital Product & Development, you will be a key technology and business leader responsible for shaping our digital ecosystem. This includes ownership of our ecommerce platform, customer-facing web and mobile apps, and internal tools that power our bakeries and operations. You will directly manage leaders across product management, engineering, and business analysis—building a high-performing, cross-functional team with a relentless focus on customer value, technical excellence, and business impact.

This role blends strategic thinking, cross-functional leadership, technical fluency, and a deep understanding of product lifecycle management. You’ll partner closely with executive leadership and stakeholders across marketing, operations, customer experience, and creative to prioritize, plan, and launch innovative solutions that move the brand forward.

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:

• Strategic Leadership & Vision

•Define and evangelize a multi-year digital product and platform strategy that aligns with Insomnia’s growth goals

•Translate company objectives into a scalable product and technical roadmap, grounded in data, insights, and innovation

•Be the internal champion for digital transformation and experience excellence across customer, bakery, and corporate touchpoints

Product & Experience Management

•Oversee the full product lifecycle: from discovery and concepting to delivery and optimization

•Ensure our ecommerce, loyalty, and mobile platforms deliver seamless, engaging, and high-converting customer experiences

•Lead usability, experimentation, and feedback loops to continuously improve the end-user journey

Engineering & Development Oversight

•Partner with the Director of Engineering to set development standards, architecture direction, and quality benchmarks

•Advocate for efficient, modern engineering practices, including CI/CD, automated testing, and cloud infrastructure

•Collaborate to balance tech debt reduction with forward-looking platform enhancements

Team Leadership & Culture

•Manage and mentor a growing team including a Product Manager, Business Analyst, and Director of Engineering

•Foster a collaborative, inclusive, high-accountability environment rooted in curiosity and results

•Recruit, develop, and retain top-tier digital talent

Cross-Functional Collaboration & Stakeholder Management

•Serve as the connective tissue between technology and business units, communicating priorities, progress, and pivots

•Partner with Marketing, Brand, and Growth to drive traffic and conversion through digital channels

•Work with Operations and Customer Experience to identify friction points and create tools that drive efficiency and satisfaction

Measurement & Optimization

•Set and track KPIs for all digital products and technical initiatives (e.g. conversion, uptime, page speed, app store ratings)

•Leverage analytics, user research, and testing to guide roadmap and feature prioritization

•Own budget planning and vendor/partner management for digital products

Desired Skills & Qualifications:

• 10+ years of progressive experience in digital product and technology leadership
• Proven success leading ecommerce or consumer-facing digital platforms (DTC or QSR experience preferred)
• Strong technical acumen and experience working directly with engineering and QA teams
• Deep understanding of agile methodologies, design thinking, and iterative product development
• Experience managing high-performing cross-functional teams in product, engineering, and analytics
• Strategic thinker who can zoom out to set vision but is also comfortable rolling up sleeves
• Excellent communication skills and comfort presenting to executive stakeholders and board-level leaders
• Data-driven mindset with strong knowledge of analytics platforms, A/B testing, and BI tools
• BA/BS in Computer Science, Engineering, or related field (MBA a plus)