Director of Digital Product

About the role

Insomnia Cookies is looking for a Director of Digital Product to lead the vision behind everything our guests tap, order, and earn points on — and everything our Cookie Crew uses behind the scenes to keep the ovens running and the app in sync. You’ll own the full product lifecycle — strategy, roadmap, execution — across digital ordering, loyalty, our mobile app, delivery, and the internal tools that keep our bakeries humming.

Consider yourself the advocate-in-chief for two very important audiences: the guest craving a warm cookie at 2am, and the Crew member making sure it gets to them.

Responsibilities

• Product strategy & vision: Work closely with stakeholders to set the vision for both our guest-facing platforms and our internal tools and systems. Ensure every roadmap ladders up to our Always Warm strategy. Translate that vision into a strategy your team, peers, and executive leadership can rally behind.
• Roadmap management: Own a single, unified roadmap spanning digital ordering, loyalty, mobile app, and delivery integrations — plus the internal tools that support store operations, People activities, and our support center. Prioritize ruthlessly and know exactly why each item is on the roadmap and its placement.
• Engineering partnership: Partner closely with Engineering Directors to turn roadmap priorities into buildable plans.
• AI & emerging tech: Spot and champion opportunities to apply AI/ML to guest-facing and in-store experiences — personalization, ordering intelligence, tools that make the Crew's shift easier — and partner with Engineering to design and build them.
• Delivery partnerships: Lead the evolution of our delivery integrations and manage commercial relationships with third-party delivery platforms, balancing guest experience, unit economics, and operational reality.
• Guest & Crew insight: Get close to the people who use what you build. Spend time in bakeries, ride along on deliveries, sit in on guest research, and build a feedback pipeline from guests and employees to shape future development.
• Marketing partnership: Collaborate with Marketing to understand their goals and brainstorm how to bring the brand — and its campaigns — to life through digital products. Ensure every guest touchpoint feels cohesive and on-brand.
• Team leadership: Build and mentor Insomnia's product management function. Hire, develop, and grow a hybrid team as the function scales.
• Performance & reporting: Approach work with a quantitative eye, defining success metrics (engagement, conversion, retention, order frequency, internal adoption) with clear goals. Lead experimentation (A/B tests, funnel analysis) and report progress to leadership regularly.

Requirements

• 8+ years in product management, including 3+ years managing a roadmap end-to-end; bachelor's degree in a related field or equivalent experience.
• QSR, retail, or multi-unit restaurant experience strongly preferred.
• Comfort with Agile/Scrum and tools like Jira, Figma, or Lucid.
• Track record of shipping features that aligned with organizational strategy and drove significant impact.
• Experience managing and developing product managers.
• Familiarity applying AI/ML in consumer product experiences (personalization, recommendation systems, LLM-powered tools).
• Ability to align Marketing, Operations, Engineering, People, and Franchise leadership, even when priorities differ.
• Zero fear of a blank page — you’ll be doing a lot of building.
• Excellent communication skills, equally comfortable in a one-pager or presenting to executive leadership.
• Willingness to travel occasionally to bakeries and support center locations to stay close to the guest and Crew experience.

Benefits

• Hybrid work environment.
• Opportunity to shape Insomnia Cookies’ next chapter of growth.
• Competitive compensation package including base, bonus, and equity.
• Comprehensive benefits: health, dental, vision, and 401(k).
• Fun, entrepreneurial, and cookie-filled culture.
• Free cookies, branded swag, and more.