At Insomnia Cookies, we believe that every bite should bring joy—and that starts with our team. We're a fast-paced, growth-driven company passionate about innovation, community, and delivering warm, delicious cookies to our customers day and night. As we continue to scale, we’re investing in the development of our people to fuel personal growth and organizational success.

We’re seeking a dynamic, strategic, and hands-on Director of Learning & Development to lead our enterprise learning strategy and help us build a culture of continuous learning. This role will drive innovative learning solutions and implement impactful development programs across both our IWP Center (Insomnia’s corporate HQ) and our nationwide bakery teams.

While the current focus of this role is on North American operations, we are growing globally, and this leader will play an integral role in expanding our learning strategy to international markets as our business scales.

The ideal candidate is passionate about building scalable programs, loves creating engaging content, and excels at collaborating across business functions to drive real results.

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:

Create a Culture of Continuous Learning: Embed a growth mindset throughout our organization by promoting learning and development as a core value across all teams—both in bakeries and at the IWP Center
Lead Learning Strategy & Needs Assessment: Conduct in-depth assessments to identify enterprise-wide learning needs. Reimagine, design, and implement comprehensive L&D programs, resources, and frameworks tailored to all employee levels. Own the full lifecycle of program development—from ideation through delivery and iteration
Deliver Scalable, Engaging Learning Experiences: Develop and deliver high-quality, accessible, and inclusive learning content that speaks to diverse learners. Facilitate interactive sessions (live and virtual) and introduce creative ways to engage team members in their own development journey, using modern, hands-on learning approaches
Implement & Evolve Learning Systems: Select, manage, and continuously improve cutting-edge learning platforms and tools that support our training infrastructure and learner experience. Leverage data and analytics to assess impact, track engagement, and report ROI to key stakeholders
Build and Lead Field Training Teams: Collaborate with Operations to develop and lead a team that is responsible for onboarding new Store Managers and delivering Train-the-Trainer programs across the field. Clarify expectations for direct versus matrixed management. Support field facilitators by providing coaching, resources, and program updates
Support New Store Openings & Operational Excellence: Partner with Cookievation (R&D), Food Safety & Quality Assurance, and Operations teams to develop training materials for new store openings, product rollouts, and operational standards
Develop Leadership & High-Potential Programs: Work with executive leadership to design, facilitate, and manage a Leadership Development Program. Identify and nurture emerging talent through targeted growth paths and experiential learning opportunities. Build programs that include succession planning and performance coaching strategies
Drive Organizational Development: Collaborate with the People team to build career-pathing frameworks, performance development tools, and organizational design strategies that support employee growth and engagement. Lead the delivery of related workshops and training sessions to embed best practices across the business

Desired Skills & Experience:

8+ years of progressive experience in L&D, talent development, or organizational development, including experience in field-based and corporate environments
Proven track record designing, launching, and scaling enterprise-wide learning strategies
Experience delivering and facilitating engaging training in both live and virtual environments
Strong leadership and team development skills, with experience managing training teams across dispersed locations
Data-driven mindset with experience using analytics to measure program effectiveness, track engagement, and drive continuous improvement
Excellent facilitation and presentation skills with audiences of all sizes
Ability to thrive in a fast-paced, high-growth company with evolving priorities
Experience with learning management systems (LMS) and modern eLearning platforms
Passion for food, retail, hospitality, or fast-casual service industries is a plus

Ready to help us develop the next generation of Insomniacs? Apply now and bring your passion for learning to the sweetest place to work.

About us:

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 rabid following of cookie lovers who crave Insomnia’s warm, delicious delivery all day and late into the night. With an expanding footprint of over 300 stores globally, an experiential, “sweet-easy” concept as the brand’s flagship in Philadelphia, Pa. (where Insomnia Cookies is headquartered), and a rapidly-growing nationwide shipping and gifting portfolio... Insomnia Cookies is revolutionizing the cookie game by truly "Imagining What’s Possible"!

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Learning & Development Director