Regional Director of Operations

Insomnia Cookies•Chicago, IL

7d•Hybrid

About The Position

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. This means knowing your numbers cold, using data and field insights to spot opportunities and risks, and having the operating judgment to act on what you find. You'll deliver results by building exceptional leaders, coaching and developing District Managers and Area Managers to operate like owners themselves. You'll set a high bar for performance while creating a culture of learning, coaching, and accountability. This role requires staying curious, challenging the status quo, embracing new ideas, and turning innovation into consistent execution across 70+ bakeries. You'll connect strategy to field execution, using a data-driven, business-first approach. Meaningful time will be spent in bakeries to understand the 'why' behind the data. Success means a region that delivers strong business results, exceptional operations, an Always Warm experience, and a deep bench of capable leaders.

Requirements

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.
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.
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; willing to roll up your sleeves and jump in when the business needs you.
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.
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.

Nice To Haves

Restaurant/QSR or high-volume food service experience
Experience overseeing 50+ locations

Responsibilities

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 field observations to understand drivers and opportunities.
Set clear regional priorities and translate company goals into focused plans for District Managers.
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 future business needs.
Quickly diagnose underperformance, address root causes, and hold leaders accountable for sustained improvement.
Lead, coach, and develop a high-performing team of District Managers.
Build leaders who can read their business, diagnose problems, make sound decisions, develop their teams, and take action with confidence.
Make coaching part of your leadership style—observe, ask questions, give feedback, recognize performance, and hold leaders accountable for results and leadership.
Create a strong culture of training and development.
Hold every leader accountable for building the next leader, creating a deep bench and strong succession pipeline.
Partner with the People team to identify and develop high-potential talent, strengthen retention, and create career growth opportunities.
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.
Stay close to the business through purposeful bakery and market visits—observing operations, coaching leaders, talking with guests and Insomniacs, and identifying improvement opportunities.
Roll up your sleeves and work alongside the team when needed to stabilize operations and understand root causes, using these moments to build capability.
Turn company strategy into great field execution, ensuring leaders understand goals and expectations.
Lead change with speed, clarity, and confidence, challenging the team to find better ways to operate.
Partner across Marketing, Finance, Digital, Supply Chain, People, Development, and other teams to execute new products, programs, technology, openings, and initiatives.
Be a strong voice for the field, bringing operating and performance data into company decisions.
Remove barriers and unnecessary complexity that hinder leaders from running great businesses, developing teams, and serving guests.