Remote Regional Operations Manager Jobs in Naperville, IL

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.
WHAT YOU'LL DO:
OWN & GROW THE BUSINESS

• Deliver the region's business plan, with accountability for achieving sales, profitability, labor, COGS, operating income, EBITDA, guest experience, and operational performance targets across 70+ bakeries.

• Know your business inside and out-using P&Ls, performance data, guest insights, and what you see in the field to understand what's driving results and where opportunities exist.

• Set clear regional priorities and translate company goals into focused plans that District Managers can execute with their teams.

• Identify opportunities to grow sales, improve productivity, manage costs, and strengthen profitability without compromising the guest or Insomniac experience.

• Recognize what's working and scale it across the region, always looking ahead to anticipate risks, opportunities, and what the business will need next.

• Quickly diagnose underperformance, address root causes, and hold leaders accountable for sustained improvement.

BUILD LEADERS WHO BUILD LEADERS

• Lead, coach, and develop a high-performing team of District Managers who own their businesses and their results.

• Build leaders who can read their business, diagnose problems, make sound decisions, develop their teams, and take action with confidence.

• Make coaching part of how you lead-observe, ask great questions, give candid feedback, recognize great performance, and hold leaders accountable for both what they deliver and how they lead.

• Create a strong culture of training and development where leaders know what great looks like and have the capability to deliver it.

• Hold every leader accountable for building the next leader, creating a deep bench and strong succession pipeline across the region.

• Partner with the People team to identify and develop high-potential talent, strengthen retention, and create opportunities for great Insomniacs to grow their careers.

DELIVER EXCEPTIONAL OPERATIONS & AN ALWAYS WARM EXPERIENCE

• Set a high bar for operational excellence across product quality, food safety, cleanliness, speed of service, hospitality, and brand standards.

• Ensure every bakery delivers an Always Warm experience for our guests, recognizing that how we deliver results matters as much as the results themselves.

• Stay close to the business through purposeful bakery and market visits-observing operations, coaching leaders, talking with guests and Insomniacs, and identifying opportunities to improve.

• Know when to coach and when to jump in. When the business needs you, roll up your sleeves and work alongside the team to stabilize the operation and understand the root cause.

• Use those moments to build capability-solving what needs to be solved today while developing leaders who can solve it themselves tomorrow.

MOVE THE BUSINESS FORWARD

• Turn company strategy into great field execution, ensuring leaders understand what we're doing, why it matters, and what great looks like.

• Lead change with speed, clarity, and confidence while challenging your team to continually find better and simpler ways to operate.

• Partner across Marketing, Finance, Digital, Supply Chain, People, Development, and other teams to successfully bring new products, programs, technology, bakery openings, and company initiatives to life.

• Be a strong voice for the field, bringing real operating and performance data into company decisions and candidly sharing what is, and isn't working.

• Remove barriers and unnecessary complexity that get in the way of our leaders running great businesses, developing their teams, and serving our guests.

Qualifications
QUALIFICATIONS:

• 10+ years of progressive multi-unit restaurant, retail, or hospitality operations experience, including 5+ years leading multi-unit field leaders such as Regional Director/District Managers or equivalent. Restaurant/QSR or high-volume food service experience strongly preferred.

• Proven success leading a large, geographically dispersed business with full P&L accountability across multiple markets; experience overseeing 50+ locations strongly preferred.

• Experience operating within small to mid-sized, high-growth companies comfortable with the pace, ambiguity, and hands on problem solving that comes with scaling a business, not just running within an already mature system.

• Strong business and financial acumen across sales, EBITDA, labor, COGS, budgeting, forecasting, and expense management with a track record of delivering results to plan.

• A proven leader of leaders who sets clear expectations, coaches with purpose, builds accountability, and develops leaders who can confidently own their businesses.

• Demonstrated success building strong teams, developing high-potential talent, strengthening succession pipelines, and promoting from within.

• A strong operator who can use data to diagnose performance, identify root causes, and turn insights into action while staying close enough to the field to know what the numbers don't tell you.

• A hands on leadership style. You know how to lead through others, but when the business needs you, you're willing to roll up your sleeves and jump in.

• Experience leading through growth and change, with the ability to turn strategy and innovation into consistent field execution.

• Strong communication, relationship-building, and influencing skills across field teams, senior leadership, and cross-functional partners.

EDUCATION & OTHER REQUIREMENTS

• Bachelor's degree preferred; equivalent relevant leadership experience will be considered.

• Ability to travel approximately 50-70%, including regular overnight travel.

• Ability to work a flexible schedule based on business needs, including evenings, late nights, weekends, and holidays.

• Ability to perform the essential functions of the role with or without reasonable accommodation.

$140,000 - $150,000 a year
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.