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Sunnyside

Retailer of medical and adult-use cannabis

Retail Store Supervisor

Full-Time
$23 - $25+ Annual discretionary bonus + Stock options
Mid
Pittsburgh, PA, USA
In Person
RetailRetail Store Management
No H1B Sponsorship

About the job

Requirements
  • High school diploma or equivalent.
  • Three to five years of customer service experience.
  • At least one year of experience leading or mentoring a team.
  • Strong customer service skills.
  • Ability to learn and apply technical and product-related information in a professional consultative manner.
  • Strong communication, interpersonal, and persuasive skills.
  • Must be at least 21 years old.
  • Must comply with all legal and company regulations for working in the industry.
  • Must be legally authorized to work in the United States permanently without current or future employment-based visa sponsorship.
Responsibilities
  • Support the day-to-day operations of the dispensary in accordance with state law and company standards.
  • Direct staff workflow and regularly perform store opening and closing procedures.
  • Manage escalated customer concerns and serve as an ambassador of the company's mission.
  • Perform store opening and closing procedures during non-peak periods, including register preparation, morning and closing inventory, inventory reconciliation, and inventory reporting.
  • Facilitate training and onboarding of Lead Wellness Advisors and Wellness Advisors, including coaching on selling and cross-selling techniques.
  • Respond to employee questions, concerns, and suggestions, and communicate team resource requirements to management.
  • Provide real-time coaching and feedback regarding performance concerns, and document and escalate employee relations issues to management in a timely manner.
  • Direct team workflow by creating morning rosters and break sheets and delegating daily responsibilities.
  • Ensure the team complies with company policies and procedures and state and local laws.
  • Manage escalated customer concerns and respond to complex or nonstandard product questions.
  • Investigate cash, point-of-sale, or product discrepancies and record or escalate them appropriately.
  • Troubleshoot technical issues or glitches in the point-of-sale system.
  • Verify inventory counts and cash deposit totals, and reconcile discrepancies.
  • Maintain inventory of marketing assets, including fliers, merchandise, and promotional materials.
  • Maintain a clean and safe environment for employees and customers.
  • Lift, carry, and balance up to 50 pounds, or up to 100 pounds with assistance, and walk or stand for extended periods.
Desired Qualifications
  • Cannabis experience is preferred.

About the company

Sunnyside is a national cannabis dispensary brand under Cresco Labs that sells medical and recreational cannabis through a network of stores across multiple states. The company operates both in-person retail and online ordering for in-store pickup, with some markets offering home delivery. Stores emphasize a bright, wellness-focused shopping environment designed to be approachable for first-time and experienced cannabis users, and they employ trained wellness advisors to help customers choose products. Sunnyside carries a wide range of products, including flower, vapes, edibles, concentrates, and topicals, featuring many Cresco-backed brands (such as Cresco, High Supply, FloraCal, Mindy’s Edibles, Good News, Wonder, and Remedi) alongside products from other operators and local producers. The goal is to normalize cannabis shopping, educate customers, and provide easy access to cannabis products as the brand expands across the U.S.

Company Size

N/A

Company Stage

N/A

Total Funding

N/A

Headquarters

Leicester, United Kingdom

Founded

2018

Simplify Jobs

Simplify's Take

What believers are saying

  • Cresco reported $173 million Q2 2026 revenue and $40 million adjusted EBITDA.
  • Sunnyside expanded to 74 stores nationwide after Aberdeen opened on May 5, 2026.
  • New Ohio stores lifted Cresco to number two retail share in the state.

What critics are saying

  • Ohio sued Cresco on February 6, 2026 over shelf-space collusion across MSOs.
  • Cresco carried $573.8 million debt on March 31, 2026, constraining expansion and pricing.
  • Federal illegality blocks a senior U.S. exchange listing, keeping capital costs elevated.

What makes Sunnyside unique

  • Sunnyside pairs Cresco’s brands with retail, controlling shelf space and customer experience.
  • Its bright, wellness-focused stores normalize cannabis shopping for first-time and repeat consumers.
  • Ohio and Florida openings in 2026 show disciplined site selection in high-traffic corridors.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • 401(k) Retirement Plan
  • 401(k) Company Match
  • Paid Holidays
  • Paid Time Off
  • Stock Options

Company News

WOWK-TV
Oct 17th, 2026
Sunnyside Dispensary opens in Prestonsburg, expanding medical cannabis access in Eastern Kentucky.

Sunnyside Dispensary opens in Prestonsburg, expanding medical cannabis access in Eastern Kentucky. Posted: Oct 16, 2026 / 08:54 PM EDT Updated: Oct 16, 2026 / 09:14 PM EDT PRESTONSBURG, Ky. (WOWK) - A new medical cannabis dispensary is now serving patients in Floyd County, becoming the first operating dispensary in Kentucky's Mountain licensing region. Sunnyside Dispensary officially opened its doors Monday, Oct. 12, after receiving approval from the Kentucky Office of Medical Cannabis on Oct. 9. With the Prestonsburg location operating, state officials say medical cannabis dispensaries are now open in all 11 licensing regions across the Commonwealth. Kentucky now has 26 operating dispensary facilities. The dispensary is located at 81 Glynview Plaza, Suite 147, in Prestonsburg and is open seven days a week. For some patients, the new location means having medical cannabis available closer to home. Scottie Gross told 13 News he began experiencing seizures more than 20 years ago and was prescribed several medications, but said he continued having seizures. "Well, I started having seizures. They had me on every kind of medication, and I mean handfuls every day. I still had them," Gross said. "Finally, my wife and I were talking one day, and she did it on her own, actually. I quit taking all of the seizure medicine and started smoking a little weed just in the morning. Haven't had one since then. That's been 20-some years now." Gross said he believes cannabis has also helped him manage pain and nerve problems and described his experience with it as life-changing. His experience is personal and should not be interpreted as medical advice. Kentucky's medical cannabis program requires patients to obtain a written certification from an authorized medical cannabis practitioner before applying for a medical cannabis card. State guidance says practitioners are required to discuss possible risks, side effects and drug interactions with patients. Kentucky legalized medical cannabis through Senate Bill 47, which took effect on Jan. 1, 2025. Recreational cannabis remains illegal in the Commonwealth. According to Governor Andy Beshear's office, more than 28,000 Kentuckians have been approved for medical cannabis cards, and more than 500 medical cannabis practitioners have registered with the state program. Sunnyside's grand opening in Prestonsburg is scheduled for Friday, Oct. 23.

Associated Press
Apr 10th, 2026
Cresco Labs opens seventh Ohio cannabis dispensary in Bridgeport

Cresco Labs has opened its seventh Ohio dispensary, Sunnyside Bridgeport, located at 435 Main Street in Bridgeport. The new location marks the company's 73rd dispensary nationwide. The store is situated in downtown Bridgeport near the Ohio River, close to I-70 and U.S. Route 40. It offers cannabis products from Cresco Labs' brand portfolio, including Cresco, Supply, Good News, Mindy's and Wonder, along with accessories. Customers aged 21 and older can shop in-store or order online for pickup. The dispensary operates daily from 9 a.m. to 9 p.m. CEO Charlie Bachtell said the opening brings the company's "education-first approach" to more consumers across Belmont County and the Ohio Valley region.