Regional Director of Operations

Insomnia Cookies•Chicago, IL

6d•$140,000 - $150,000

About The Position

The Regional Director of Operations owns the performance of more than 70 Insomnia Cookies bakeries, with accountability for regional sales, profitability, operational excellence, guest experience, and people results. The role runs the region as a business, using P&Ls, performance data, guest insights, and field observations to identify opportunities and risks, set priorities, and deliver sustained improvement. The director leads, coaches, and develops District Managers and other field leaders, building a culture of accountability, learning, and leadership development. The role translates company strategy and innovation into consistent field execution, stays close to bakery operations through regular visits, and partners with cross-functional teams to advance products, programs, technology, openings, and company initiatives. The position requires approximately 50–70% travel, including regular overnight travel, and a flexible schedule that may include evenings, late nights, weekends, and holidays. The posted annual salary range is $140,000–$150,000.

Requirements

10 or more years of progressive multi-unit restaurant, retail, or hospitality operations experience.
At least 5 years leading multi-unit field leaders, such as Regional Directors or District Managers, or equivalent.
Proven success leading a large, geographically dispersed business with full P&L accountability across multiple markets.
Experience in small to mid-sized, high-growth companies, including comfort with the pace, ambiguity, and hands-on problem solving involved in scaling a business.
Strong financial and business acumen across sales, EBITDA, labor, COGS, budgeting, forecasting, and expense management, with a record of delivering results to plan.
Ability to set clear expectations, coach with purpose, build accountability, and develop leaders who can own their businesses.
Success building teams, developing high-potential talent, strengthening succession pipelines, and promoting from within.
Ability to use data to diagnose performance, identify root causes, and turn insights into action while remaining connected to field operations.
Hands-on leadership style and willingness to work alongside teams when needed.
Experience leading through growth and change and translating strategy and innovation into field execution.
Strong communication, relationship-building, and influencing skills across field teams, senior leadership, and cross-functional partners.
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.

Nice To Haves

Restaurant/QSR or high-volume food service experience.
Experience overseeing 50 or more locations.
Bachelor’s degree; equivalent relevant leadership experience will be considered.

Responsibilities

Deliver the region’s business plan and achieve sales, profitability, labor, COGS, operating income, EBITDA, guest experience, and operational performance targets across more than 70 bakeries.
Use P&Ls, performance data, guest insights, and field observations to understand business results and identify opportunities.
Set regional priorities and translate company goals into focused plans for District Managers and their teams.
Identify ways to grow sales, improve productivity, manage costs, and strengthen profitability without compromising the guest or Insomniac experience.
Scale successful practices across the region and anticipate business risks and opportunities.
Diagnose underperformance, address root causes, and hold leaders accountable for sustained improvement.
Lead, coach, and develop District Managers and other field leaders to own their businesses and results.
Provide observation, questioning, candid feedback, recognition, and accountability through regular coaching.
Build a culture of training and development and ensure leaders develop future leaders and succession candidates.
Partner with the People team to identify and develop talent, strengthen retention, and support employee career growth.
Maintain high standards for product quality, food safety, cleanliness, speed of service, hospitality, and brand standards.
Ensure bakeries deliver an Always Warm guest experience.
Visit bakeries and markets to observe operations, coach leaders, engage with guests and employees, and identify improvement opportunities.
Work alongside teams when needed to stabilize operations, resolve root causes, and build leaders’ capability.
Translate company strategy into effective field execution and lead change with speed, clarity, and confidence.
Partner with Marketing, Finance, Digital, Supply Chain, People, Development, and other teams on products, programs, technology, bakery openings, and company initiatives.
Represent field perspectives in company decisions using operating and performance data, and communicate what is and is not working.
Remove barriers and unnecessary complexity that impede leaders’ ability to run their businesses, develop teams, and serve guests.