Regional Director of Operations

Insomnia Cookies; Chicago (IL); On-site; USD 140,000 - 190,000; Full time

Job summary

Insomnia Cookies is seeking a Regional Director of Operations to own the performance of 70+ bakeries, driving sales, profitability, guest experience, and people results across the region. You’ll coach District and Area Managers, read the business, and translate data into action.

You’ll stay close to the action in stores, ensuring the leadership engine delivers consistent growth and operational excellence. This role demands strategic thinking, hands-on leadership, and a relentless focus on

Qualifications

• Leads large multi-unit operations across 70+ bakeries.
• Coaches and develops District and Area Managers to own their business results.
• Uses data and field insights to identify opportunities and risks.

Responsibilities

• Own region performance across sales, profitability, and guest experience.
• Coach leaders and build a high-performing leadership bench.
• Translate strategy into action in a fast-moving environment.
• Stay close to bakery operations to ensure consistent execution.

Skills

Leadership

People management

Data-driven

Budgeting

Operations management

Strategic planning

Job description

ABOUT INSOMNIA

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 350 stores globally, an experiential, "sweet-easy" flagship concept, and large scale operations and delivery capabilities ... Insomnia Cookies is revolutionizing the cookie game by truly "Imagining What's Possible"!

ABOUT THE ROLE

As a Regional Director of Operations, you'll own the performance of 70+ Insomnia bakeries, with accountability for delivering strong sales, profitability, operational excellence, guest experience, and people results across your region. You'll run your region like a business you own, not just a set of bakeries you oversee. That means knowing your numbers cold, using data and field insights to spot where the real opportunities and risks are before they show up in a monthly report, and having the operating judgment to act on what you find. You won't wait for something to break, you'll be looking for the next win as hard as you're watching for the next problem.

You'll deliver those results by building exceptional leaders. You'll coach, teach, and develop District Managers and Area Managers to operate like owners themselves, reading their own business, making sound calls with incomplete information, building strong teams, and taking accountability for results without waiting to be told. You'll set a high bar for performance while creating a culture of learning, coaching, and accountability, where leaders know what great looks like and are constantly building the next generation of Insomnia leaders behind them.

This is a big, fast-moving business, and you'll be expected to move with it. You'll stay curious, challenge the status quo, embrace new ideas, and turn innovation into consistent execution across 70+ bakeries. You'll connect strategy to what actually happens in our bakeries, and you'll bring the same data-driven, business-first thinking to that translation, not just passing down direction, but making sure it's grounded in what your numbers and your field time are actually telling you.

And you'll stay close to the action. You'll spend meaningful time in our bakeries with our leaders and guests, because the data tells you what is happening, but time in the field tells you why.

Success means a region that delivers, strong business results, exceptional operations, an Always Warm experience for our Insomniacs, and a deep bench of capable leaders who know how to own their businesses.

EQUAL EMPLOYMENT OPPORTUNITY

Insomnia Cookies is an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace where everyone feels welcome. We consider all qualified applicants for employment without regard to race, color, religion, sex (including pregnancy, sexual orientation, or gender identity), national origin, age, disability, genetic information, veteran status, or any other protected characteristic under applicable federal, state, or local law.

REASONABLE ACCOMMODATION

If you require a reasonable accommodation during any part of the application or hiring process, please let us know. We are committed to providing reasonable accommodations to qualified individuals with disabilities.

READY TO IMAGINE WHAT'S POSSIBLE?

This is more than running a region. It's building the leadership engine that helps Insomnia grow.

You'll develop the leaders who develop our teams. You'll shape the experience thousands of Insomniacs create for our guests every day. And you'll help ensure that as we grow, every bakery still feels unmistakably Insomnia.

If you're ready to lead with warmth, coach with purpose, stay curious, move fast, and build teams that deliver incredible results, we'd love to meet you.

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"!

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.