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Insomnia Cookies

Late-night delivery of cookies to students

Regional Director of Operations

Full-TimeUpdated on 10/23/2026
$140k - $150k/yr
Expert
Bachelor's
Detroit, MI, USA
RemoteApproximately 50–70% travel, including regular overnight travel.
Business & Strategy

About the job

Requirements
  • At least 10 years of progressive multi-unit restaurant, retail, or hospitality operations experience, including 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 operating within small- to mid-sized, high-growth companies and comfort with the pace, ambiguity, and hands-on problem solving involved in scaling a business.
  • Strong business and financial acumen across sales, EBITDA, labor, cost of goods sold, budgeting, forecasting, and expense management, with a track record of delivering results to plan.
  • Ability to set clear expectations, coach with purpose, build accountability, and develop leaders who can own their businesses.
  • Demonstrated success building strong 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 staying connected to field operations.
  • Hands-on leadership style, including willingness to work alongside teams when the business needs it.
  • Experience leading through growth and change and turning strategy and innovation into consistent field execution.
  • Ability to communicate, build relationships, and influence 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.
Responsibilities
  • Deliver the region’s business plan and achieve sales, profitability, labor, cost of goods sold, operating income, EBITDA, guest experience, and operational performance targets across more than 70 bakeries.
  • Use profit and loss statements, 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 to execute with their teams.
  • Identify opportunities to grow sales, improve productivity, manage costs, and strengthen profitability while maintaining the guest experience.
  • Scale successful practices across the region and anticipate business risks, opportunities, and future needs.
  • Diagnose underperformance, address root causes, and hold leaders accountable for sustained improvement.
  • Lead, coach, and develop a high-performing team of District Managers who own their businesses and results.
  • Build leaders’ capability to interpret business performance, diagnose problems, make decisions, develop teams, and take action.
  • Observe leaders, ask questions, provide candid feedback, recognize performance, and hold leaders accountable for results and leadership practices.
  • Create a culture of training and development with clear expectations for performance.
  • Hold leaders accountable for developing future leaders and building a succession pipeline across the region.
  • Partner with the People team to identify and develop high-potential talent, strengthen retention, and create career-growth opportunities.
  • Set operational standards across product quality, food safety, cleanliness, speed of service, hospitality, and brand standards.
  • Ensure every bakery delivers the company’s Always Warm guest experience.
  • Visit bakeries and markets to observe operations, coach leaders, speak with guests and employees, and identify improvement opportunities.
  • Work alongside bakery teams when needed to stabilize operations and identify root causes.
  • Use operational challenges to build leaders’ capability to solve future problems independently.
  • Translate company strategy into field execution and ensure leaders understand priorities and performance expectations.
  • Lead change and encourage teams to find better and simpler ways to operate.
  • Partner with Marketing, Finance, Digital, Supply Chain, People, Development, and other teams to launch products, programs, technology, bakery openings, and company initiatives.
  • Represent field perspectives in company decisions using operating and performance data, and communicate candidly about what is and is not working.
  • Remove barriers and unnecessary complexity that hinder leaders from running businesses, developing teams, and serving guests.
Desired Qualifications
  • Restaurant, quick-service restaurant, or high-volume food service experience is strongly preferred.
  • Experience overseeing 50 or more locations is strongly preferred.
  • A bachelor’s degree is preferred; equivalent relevant leadership experience will be considered.

About the company

Insomnia Cookies delivers warm, freshly baked cookies late at night, mainly to college students, through a mix of company-owned bakeries and franchised locations. Cookies are baked on-site and delivered or available for pickup, focusing on a late-night window to ensure warm, fresh treats. The company differentiates itself with a dedicated late-night delivery niche and a scalable franchise program that provides standardized systems, training, and marketing support. Its goal is to grow both company locations and franchisees to expand its footprint and revenue as the top choice for late-night, warm cookies.

Company Size

1,001-5,000

Company Stage

Acquired

Total Funding

$4.4M

Headquarters

East Norriton Township, Pennsylvania

Founded

2003

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Simplify Jobs

Simplify's Take

What believers are saying

  • Insomnia opened Red Bank on September 1, 2026, extending New Jersey coverage.
  • Management targeted more than 75 new locations in 2026, accelerating a 370-store base.
  • August 11, 2026 free-cookie giveaway for 30,000 freshmen deepens campus loyalty and trials.

What critics are saying

  • July 27, 2026 wage litigation hit delivery-driver claims; labor costs stay under attack.
  • Delayed Staten Island openings show permitting and execution problems can slow expansion.
  • If delivery-unit economics deteriorate, the 1,800-store plan becomes an existential overreach.

What makes Insomnia Cookies unique

  • Late-night warm-cookie delivery still defines Insomnia Cookies, unlike daytime dessert chains.
  • University-adjacent stores capture college students at midnight, when pizza and sandwich chains compete.
  • 2026 collaborations with Hostess and Supergirl create collectible, app-driven demand spikes.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Pet Insurance
  • 401(k) Company Match
  • Paid Vacation
  • Unlimited Paid Time Off
  • Hybrid Work Options

Growth & Insights and Company News

6 month growth

0%

1 year growth

0%

2 year growth

15%
Daily Voice
Sep 2nd, 2026
Insomnia Cookies opens in Red Bank.

Insomnia Cookies opens in Red Bank. The Jersey Shore just got a little bit sweeter. 09/02/2026 11:24 a.m. Insomnia Cookies opened a location in Red Bank on Tuesday, Sept. 1 at 74 Broad St. The bakery expands Insomnia's footprint in the Garden State and promises to offer signature warm cookies and decadent desserts. The Red Bank bakery will celebrate its grand opening later this month with giveaways and special offers. Those interested in working as part-time cookie crew members, delivery drivers and shift leaders can apply here.

App.com
Sep 1st, 2026
Midnight craving? Insomnia Cookies now open in Red Bank.

Midnight craving? Insomnia Cookies now open in Red Bank. Asbury Park Press Sept. 1, 2026, 3:00 p.m. ET * Insomnia Cookies just opened its new bakery on Broad Street in Red Bank. * It's the chain's first location in Monmouth County, and eighth in New Jersey. * The bakery is in its soft opening, with a grand opening scheduled later this month. RED BANK - Midnight cookie craving? No problem. Insomnia Cookies just opened its new bakery on Broad Street in Red Bank. It's the chain's first location in Monmouth County, and eighth in New Jersey. Insomnia is known for serving warm freshly-baked treats until the early-morning hours, including late-night delivery. The downtown Red Bank opening, at 4 p.m. on Tuesday, Sept. 1, is a soft opening, with a grand opening celebration planned for later this month with giveaways and special offers, the company says. The store announced plans for its arrival in February. "Here to satisfy sweet cravings day and night, Insomnia Cookies offers in-store ordering, pickup and local delivery, with a menu featuring warm, fresh-baked cookies, Cookies IN Ice Cream, brownies, blondies, brookies, cookie cakes, vegan options and a rotating lineup of limited-time flavors," according to a news release. Customers can download the Insomnia Cookies app to place orders for pickup or delivery, track their order, save favorites and access exclusive offers. Insomina Cookies in Red Bank also is hiring part-time Cookie Crew members, delivery drivers and shift leaders. Interested applicants should visit Careers.InsomniaCookies.com. Insomnia Cookies is located at 74 Broad St., Red Bank. Hours are noon to 1 a.m. Sundays; 11 a.m. to 1 a.m. Mondays to Wednesdays; 11 a.m. to 3 a.m. Thursdays and Fridays and noon to 3 a.m. Saturdays. Visit insomniacookies.com/store/red for more information. Ilana Keller is an award-winning journalist and lifelong New Jersey resident who loves Broadway and really bad puns. Reach out: [email protected].

Sweets & Snacks World
Jun 18th, 2026
Insomnia Cookies releases Supergirl themed limited-edition cookies.

Insomnia Cookies releases Supergirl themed limited-edition cookies. Posted 18 June, 2026 pic: Insomnia Cookies In celebration of DC Studios' highly anticipated new film, releasing in cinemas on 26 June 2026, Insomnia Cookies is launching two limited-edition cookies inspired by memorable elements from the film. Available beginning 16 June at participating bakeries, the partnership introduces: * Red Velvet Revenge - A red velvet cookie filled with a hidden blue sugar cookie dough centre, topped with red velvet crumble. Inspired by the signature blue slushie from Supergirl's galactic rest stop. * Lemon Solar Punch - A lemon cookie filled with fresh strawberry jam and finished with a toasted honey crumble. Inspired by the powerful yellow suns that ignite Supergirl's super-abilities, this cookie offers a sweet, citrus-forward flavour experience. Both cookies will be available for a limited time, while supplies last.

93.3 WMMR Philadelphia
May 29th, 2026
Insomnia Cookies to open 19th Greater Philadelphia store.

Insomnia Cookies to open 19th Greater Philadelphia store. Insomnia Cookies, the Philadelphia-based late-night cookie brand founded in 2003, is expanding with its 19th store in the Greater Philadelphia area. The new location at 2329 Cottman Ave., near Holy... Published May 29, 2026 10:14 AM EDT Insomnia Cookies, the Philadelphia-based late-night cookie brand founded in 2003, is expanding with its 19th store in the Greater Philadelphia area. The new location at 2329 Cottman Ave., near Holy Family University, will continue its warm-cookie concept, offering ice cream, brownies, blondies, and vegan options. According to What Now Philadelphia, Insomnia Cookies is the brand's 26th store in Pennsylvania and its 362nd nationwide, maintaining the late-night bakery model with in-store pickup and late-night delivery, and rotating limited-time flavors. The new store will host an opening day celebration on Saturday, May 30, from noon until 3 a.m. Insomnia Rewards members will be eligible to receive one free classic cookie during the opening event, with no purchase required. To celebrate the new location, free delivery will be offered through June 15 using the code "COTTMAN." Delivery hours will extend late into the night, from 1 a.m. Sunday through Wednesday, and 3 a.m. Thursday through Saturday. It will open at noon on Saturdays and Sundays and at 11 a.m. on weekdays.

Bake Magazine
May 20th, 2026
Insomnia Cookies launches ice cream-inspired cookies for summer.

Insomnia Cookies launches ice cream-inspired cookies for summer. 05.20.2026 Insomnia Cookies is providing a nostalgic spin on summer treats with its new limited-time cookie flavors, inspired by the classic ice cream truck treats BakeMag all grew up chasing down the street. Available starting now at bakeries nationwide, the lineup includes: * Double Dip Crunch Classic: The classic warm weather treats reimagined, featuring a brown sugar cookie dough, loaded with milk chocolate chunks, crispy waffle cone pieces, roasted peanuts and peanut butter chips * Éclair the Day Off Classic: A soft brown sugar cookie dough surrounds a rich chocolate cream filling, finished with a chocolate crumb on top * Summer Strawberry Classic: Features a buttery sugar cookie dough filled with sweet strawberry filling, topped with golden strawberry crumb Customers can enjoy their favorite summer snack with a $7 deal on all Classic Cookie'wiches, now through May 31. The offer is available in-store, through delivery and online orders at all Insomnia Cookies nationwide. Get better retail baking industry search results. Adding BakeMag tells Google to prioritize bake stories.