Full-Time

Loss Prevention Specialist

Sunnyside

Sunnyside

Retailer of medical and adult-use cannabis

Compensation Overview

$30 - $38/hr

No H1B Sponsorship

Chicago, IL, USA

In Person

Category
Security & Protective Services
Required Skills
Risk Management
Data Analysis
Requirements
  • Associate’s degree/Bachelor’s Degree
  • 1-3 years of relevant work experience in loss prevention
  • 1+ years exception-based reporting, guard management, remote video monitoring systems
  • Experience in a high growth and complex industry or company and must have the ability to adapt to face-paced, highly dynamic business environments.
  • Highly motivated, self-directive, innovative, and able to work independently or among teams with resourcefulness.
  • Acts with a clear sense of integrity, ownership and accountability, ensuring stakeholders are clear on the role risk management will play in support of their goals.
  • Strong business acumen including data analytics, attention to detail, excellent communication and interpersonal skills as well as end-to-end project management.
  • Must be 21 years of age or older to apply
  • Must comply with all legal or company regulations for working in the industry
  • The company does not offer employment-based visa sponsorship for this role or any other position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without the need for current or future sponsorship at any time.
  • Genuine interest in and passion for the cannabis industry is required.
Responsibilities
  • Review and investigate incident reports involving theft, customer issues, safety, and policy violations
  • Conduct detailed CCTV and camera footage reviews to support investigations and compliance verification
  • Fulfill and manage video request tickets from internal and external teams
  • Manage contracted security vendors ensuring coverage where required and supplemental coverages for overnight projects
  • Analyze exception-based reporting (EBR) to identify transaction anomalies, fraud, and internal risk indicators
  • Cross-reference EBR data with video footage and incident reports to build complete case findings
  • Review and document all refusal-to-serve incidents to ensure compliance with state cannabis regulations and company policies
  • Identify trends and patterns in incidents, refusals, and reporting data to proactively mitigate risk
  • Conduct internal investigations related to employee misconduct, cash handling issues, and policy violations
  • Maintain accurate, detailed, and audit-ready case documentation and investigation reports
  • Escalate significant findings and compliance risks to Risk leadership and cross-functional partners
  • Partner with Operations, Compliance, and HR to resolve investigations and improve adherence to procedures
  • Monitor camera system effectiveness and report gaps, blind spots, or technical issues
  • Support regulatory and internal audits by providing documentation, video evidence, and case summaries
  • Recommend process improvements to reduce shrink, enhance compliance, and strengthen internal controls
Desired Qualifications
  • LPQ/LPC/CFI/CPP certifications are preferred

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 Labs' vertical integration ensures reliable house brand inventory supply.
  • Strategic high-traffic locations attract new and existing recreational consumers.
  • Online platform sunnyside.shop drives convenient pickup and delivery sales.

What critics are saying

  • Trulieve's 300+ stores undercut Sunnyside's pricing in Florida and Pennsylvania.
  • Illinois wholesale prices dropped 40% from 2021-2024, eroding margins.
  • New York's illicit shops capture 60% market, stalling Sunnyside expansion.

What makes Sunnyside unique

  • Sunnyside normalizes cannabis shopping with bright, welcoming dispensaries since Philadelphia 2019.
  • Wellness advisors educate customers on products like Cresco's Mindy's and High Supply.
  • Over 70 stores in seven states offer online ordering and in-store pickup.

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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

The 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.