Director Of Digital Operations Jobs (NOW HIRING)

Insomnia Cookies was founded in a college dorm room by then-student, Seth Berkowitz. Fast forward 20 years and so... many....cookies... later, our innovative bakery + delivery concept has become a cult brand known for its rabidfollowing ofcookie lovers who crave Insomnia's warm, delicious delivery all day and late into the night. With an expanding footprint of over 350 stores globally, an experiential, "sweet-easy" flagship concept, and large scaleoperations and delivery capabilities ... Insomnia Cookies is revolutionizing the cookie game by truly "Imagining What's Possible"!

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. 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.

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.

• Product strategy & vision. Work closely with stakeholders to set the vision for both our guest-facing platforms and our internal tools and systems. Make sure every roadmap ladders up to our Always Warm strategy. Translate that vision into a strategy your team, your peers, and our executive leadership can all 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, our People activities, and our support center. Prioritize ruthlessly and know exactly why each item is on the roadmap and why it's where it is. Sequencing against engineering capacity in collaboration with our engineering leadership.


• Engineering partnership. Partner closely with our 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. Take a lead role in evolving our delivery integrations, and in managing and improving our commercial relationships with third-party delivery platforms — balancing guest experience, unit economics, and operational reality.


• Guest & Crew insight. Get close to the people who actually use what you build. Spend time in bakeries, ride along on deliveries, sit in on guest research, and build a steady pipeline of feedback from guests and employees that shapes what gets built next.


• Marketing partnership. Partner with Marketing to deeply understand what they're trying to accomplish, then brainstorm together on how to bring the brand — and the specific brand moments and campaigns behind it — to life through our digital products. Be the connective tissue that makes a campaign in someone's inbox actually match what they see when they open the app, and every guest touchpoint feels like one 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 the work with a quantitative eye and a deep understanding of the metrics that underpin our digital success. Define what good looks like (engagement, conversion, retention, order frequency, internal adoption) with clear, pass/fail goals and named owners. Lead experimentation and optimization efforts — A/B tests, funnel analysis, and continuous iteration — to turn those metrics into momentum, and report progress up to leadership on a regular cadence.

• 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 the tools that go with it (Jira, Figma, Lucid, or similar)


• A track record of shipping features — guest-facing or behind-the-scenes — that aligned with organizational strategy and helped drive significant impact.


• Experience managing and developing product managers


• Familiarity applying AI/ML in consumer product experiences (personalization, recommendation systems, LLM-powered tools) — you don't need to build the model, but you need to know what's possible and how to scope it


• The instincts to get Marketing, Operations, Engineering, People, and Franchise leadership rowing in the same direction, even when they don't naturally agree


• Zero fear of a blank page — you'll be doing a lot of building!


• Excellent communication skills, equally comfortable in a one-pager or in front of executive leadership


• Willingness to travel occasionally to bakeries and support center locations to stay close to the guest and Crew experience

• Hybrid Work Environment


• Opportunity to be a major part of Insomnia Cookies’ next chapter of growth.


• Competitive compensation package including base, bonus, and equity.


• Comprehensive benefits including health, dental, vision, and 401(k).


• A fun, entrepreneurial, and cookie-filled culture.


• Free cookies, branded swag and so much more!

$150,000 - $180,000 a year