Regional Director of Operations: Lead 70+ Bakeries

Insomnia Cookies, LLC; Chicago (IL); On-site; USD 140,000 - 150,000; Full time

Job summary

Insomnia Cookies seeks a Regional Director of Operations to own the performance of 70+ bakeries, driving sales, profitability, guest experience and people results across the region. You will coach District and Area Managers, translating company goals into actionable regional plans and fostering a culture of learning and accountability.

You’ll be in the field with leaders and guests, using data to diagnose issues, seize opportunities, and build a bench of capable leaders who own their businesses.

Qualifications

• 10+ years of progressive multi-unit restaurant, retail, or hospitality operations experience.
• 5+ years leading multi-unit field leaders such as Regional Director/District Managers or equivalent.
• Experience operating with full P&L accountability across multiple markets.
• Bachelor’s degree preferred; equivalent leadership experience will be considered.

Responsibilities

• Deliver the region’s business plan with accountability for sales, profitability, labor, COGS, operating income, EBITDA, guest experience, and operational performance targets across 70+ bakeries.
• Lead, coach, and develop District Managers who own their businesses and their results.
• Set 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, anticipating risks and opportunities while staying close to field data.

Skills

Multi-unit leadership

P&L ownership

Data-driven

Travel-heavy

Education

Bachelor’s degree

Job description

ABOUTINSOMNIA:

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, andlarge scaleoperations 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'llown the performance of 70+ Insomnia bakeries, with accountability for delivering strong sales, profitability, operational excellence, guest experience, andpeopleresults across your region.You'llrun 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 judgmentto acton what you find. Youwon'twait for something tobreak,you'llbe looking for the next win as hard asyou'rewatching for the next problem.

You'lldeliver those results by building exceptional leaders.You'llcoach, teach, and develop District Managers and Area Managers tooperatelike 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'llset 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, andyou'llbe expected to move with it.You'llstay curious, challenge the status quo, embracenew 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.

Andyou'llstay close to the action.You'llspend meaningful time in our bakeries with our leaders andguests, becausethe data tells youwhatis happening, but time in the field tells youwhy.

Success means a region thatdelivers,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 understandwhat’sdriving results and where opportunities exist.

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

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

• Recognizewhat’sworking and scale it across the region, always looking ahead toanticipaterisks, 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 canreadtheir 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, recognizegreat 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 toidentifyand 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—observingoperations, coaching leaders, talking with guests and Insomniacs, andidentifyingopportunities 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 whatwe’redoing, 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 tooperate.

• 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 operatingand performance data into company decisions and candidlysharingwhat is, andisn’tworking.

• 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 asRegionalDirector/District Managers or equivalent.Restaurant/QSR or high-volume food service experiencestronglypreferred.

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

• Experienceoperatingwithinsmall tomid-sized, high-growth companiescomfortable 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 managementwitha track recordof delivering results to plan.

• A proven leader of leaders whosetsclear 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,identifyroot causes, and turn insights into actionwhile staying close enough to the field to know what the numbersdon’ttell you.

• Ahandsonleadership style. You know how to lead through others, but when the business needs you,you’rewilling 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 travelapproximately 50–70%, including regular overnight travel.

• Ability toworka 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 Cookiesisan 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 requirea reasonableaccommodation 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’sbuilding the leadership engine that helps Insomnia grow.

You’lldevelop the leaders who develop our teams.You’llshape the experience thousands of Insomniacs create for our guests every day. Andyou’llhelp ensure that as we grow, every bakery still feels unmistakably Insomnia.

Ifyou’reready to lead with warmth, coach with purpose, stay curious, move fast, and build teams that deliver incredible results,we’dlove 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"!