Job Information
Walgreens Sr. Security Specialist II-Offensive Security & Adversary Simulation in DEERFIELD, Illinois
Job Description:
Job Summary
Are you a skilled offensive security professional with a passion for ethical hacking and adversary simulation? We’re looking for a Red Team Specialist to execute advanced penetration tests, threat emulation exercises, and real-world attack simulations across our large-scale eCommerce platform. In this role, you’ll work alongside a team of security experts to uncover vulnerabilities in web applications, cloud environments, and critical business systems, helping to strengthen our defenses against sophisticated cyber threats. Your work will directly contribute to protecting sensitive customer data, including regulated health information, in a fast-paced, high-impact environment.
As a key member of the Red Team, you will collaborate with threat intelligence, blue teams, and security engineers to test and challenge our security controls. You’ll leverage your expertise in penetration testing, cloud security, and offensive security tooling to identify gaps and provide actionable insights that enhance our overall security posture. If you enjoy thinking like an attacker, solving complex security challenges, and working with cutting-edge offensive security techniques, we’d love to have you on our team!
Leads threat detection by identifying threats at the first phase of an attack or compromise. Detects threat actor activity including exploitation and risk to critical systems.
Monitors specific cyber threat actors to understand their tactics and techniques.
Utilizes data analysis, threat intelligence and cutting-edge security technologies to find unusual behavior and malicious activity.
Leads the hunt for hidden and unidentified threats to the organization’s cyber environment.
Tracks down the malicious agents who are already in a network and removes them from the environment once discovered.
Works with security monitoring tools such as firewalls, data loss prevention, network intrusion detection and antivirus software.
Uses a hypothesis-driven approach and behavioral analysis to uncover connections and correlations between potential cyber threats.
Reviews audit logs to identify unusual behavior in the network and endpoint devices. Documents findings and incident investigations. Provides feedback and training to improve security controls.
Leads in assessing network vulnerabilities and identifying critical security flaws by testing and validating the security of the network and/or testing the network to understand where vulnerabilities exist and where corrections are needed
About Walgreens
Founded in 1901, Walgreens (www.walgreens.com) has a storied heritage of caring for communities for generations, and proudly serves nearly 9 million customers and patients each day across its approximately 8,500 stores throughout the U.S. and Puerto Rico, and leading omni-channel platforms. Walgreens has approximately 220,000 team members, including nearly 90,000 healthcare service providers, and is committed to being the first choice for retail pharmacy and health services, building trusted relationships that create healthier futures for customers, patients, team members and communities.
Walgreens is the flagship U.S. brand of Walgreens Boots Alliance, Inc. (Nasdaq: WBA), an integrated healthcare, pharmacy and retail leader. Its retail locations are a critical point of access and convenience in thousands of communities, with Walgreens pharmacists playing a greater role as part of the healthcare system and patients’ care teams than ever before. Walgreens Specialty Pharmacy provides critical care and pharmacy services to millions of patients with rare disease states and complex, chronic conditions.
The actual salary an employee can expect to receive, plus bonus pursuant to the terms of any bonus plan if applicable, will depend on experience, seniority, geographic location, and other factors permitted by law. To review benefits, please visit jobs.walgreens.com/benefits More Company information is available at www.walgreensbootsalliance.com
Job ID: 1577649BR
Title: Sr. Security Specialist II-Offensive Security & Adversary Simulation
Company Indicator: Walgreens
Employment Type:
Job Function: Information Technology
Full Store Address: 108 WILMOT RD,DEERFIELD,IL 60015
Full District Office Address: 108 WILMOT RD,DEERFIELD,IL,60015-05145-01108-2
External Basic Qualifications:
Bachelor’s degree and at least 5 years of Information/Cyber Security experience OR a High School Diploma/GED and at least 7 years of Information/Cyber Security experience
Experience presenting to and interacting with the Executive level.
At least 4 years of Cyber Security experience in at least three of the following: Active threat hunting (open source or commercial tooling), Intrusion analysis, Managed or enterprise information security services, Incident response, Endpoint forensics (Windows, MAC, or Linux), Malware analysis, Penetration testing, Network defense, Threat hunting, Information security consulting
Experience establishing & maintaining relationships with individuals at all levels of the organization, in the business community & with vendors.
Experience analyzing and reporting data in order to identify issues, trends, or exceptions to drive improvement of results and find solutions.
At least 2 years of experience contributing to financial decisions in the workplace.
At least 2 years of direct leadership, indirect leadership and/or cross-functional team leadership.
Willing to travel up to/at least 10% of the time for business purposes (within state and out of state).
Preferred Qualifications:
Penetration Testing Experience – Strong background in network, web application, and cloud penetration testing, with a focus on identifying and exploiting vulnerabilities.
Red Team & Adversary Simulation – Hands-on experience executing threat emulation and real-world attack scenarios using tools like Cobalt Strike, Sliver, Metasploit, and BloodHound.
Cloud Security Knowledge – Experience testing cloud environments (AWS, Azure, GCP), including IAM abuse, misconfigurations, and privilege escalation techniques.
Custom Exploit Development – Ability to develop and modify exploits, scripts, and payloads for penetration testing and red teaming engagements.
Malware & Evasion Tactics – Knowledge of custom payloads, C2 frameworks, obfuscation, and AV/EDR evasion techniques.
Secure Coding & Web App Testing – Familiarity with OWASP Top 10, API security, and application-layer attacks to assess software security.
Active Directory & Privilege Escalation – Understanding of Windows and Linux attack vectors, including Kerberoasting, LLMNR poisoning, and credential theft techniques.
Threat Intelligence Integration – Ability to use MITRE ATT&CK and other frameworks to align offensive testing with real-world attack methodologies.Report Writing & Communication – Strong skills in documenting findings and presenting technical risks to security teams and business stakeholders.
Experience in Regulated Environments – Understanding of compliance requirements related to PCI-DSS, HIPAA, and data privacy regulations in offensive security testing.
Collaboration with Blue Teams & Engineers – Experience working with SOC teams, DFIR analysts, and security engineers to validate findings and improve detection capabilities.
Automation & Scripting – Proficiency in Python, PowerShell, or Bash for automating security testing tasks.
Bachelor’s degree and at least 5 years of Information/Cyber Security experience OR a High School Diploma/GED and at least 7 years of Information/Cyber Security experience
Experience presenting to and interacting with the Executive level.
At least 4 years of Cyber Security experience in at least three of the following: Active threat hunting (open source or commercial tooling), Intrusion analysis, Managed or enterprise information security services, Incident response, Endpoint forensics (Windows, MAC, or Linux), Malware analysis, Penetration testing, Network defense, Threat hunting, Information security consulting
Experience establishing & maintaining relationships with individuals at all levels of the organization, in the business community & with vendors.
Experience analyzing and reporting data in order to identify issues, trends, or exceptions to drive improvement of results and find solutions.
We will consider employment of qualified applicants with arrest and conviction records.
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