Senior Director, Offensive Security

Walgreens
Deerfield, IL
Job Summary

Leads a team of security professionals responsible for simulating attacks to identify and exploit vulnerabilities within WBA’s systems, networks and applications. Leads the design and execution of comprehensive attack scenarios, conducting penetration testing, routine vulnerability scanning, and
assessing the effectiveness of existing security measures. Partners with other information security and IT teams to ensure a holistic approach to security, as well as preparing detailed reports and recommendations to leaders to mitigate risks and strengthen defenses.

Job Responsibilities
  • Leads the Offensive Security (Red Team) in conducting simulated attacks of WBA’s systems, networks and applications.
  • Develops and maintains a clear roadmap to ensure progress against strategic and tactical initiatives and priorities . Provides regular and reoccurring updates to GCISO and CIO as required and or requested.
  • Stays updated on the latest cyber threats, attack techniques, and defense strategies, providing strategic insights to enhance WBA’s security posture.
  • Works closely with other members of the Information Security team, ITGRC and Privacy and supports the GCISO as part of the WBA Data Security Event Process (DSEP).
  • Develops, maintains and executes against an overall global Offensive Security strategy
  • Develop inclusive teams in which people are empowered to succeed and partnership is encouraged. Supports a high performance culture, ensure appropriate training for engineeringstaff, provide regular communications to your team and external partners, represent the firm to outside agencies and partner companies as required
  • Stay abreast of technology trends and cutting edge ideas to ensure an eye to the future. Network and maintain relationships with known industry experts and leaders
  • Leverages and maintains vendor relationships strategically to compliment offensive security capabilities. Oversees the management of Service Level Agreement (SLA) and relationship with all global entities providing these services
  • Develops comprehensive, accurate reports and presentations for both technical and executive level audiences.
  • Leverages automation, continuously developing and maintaining a mature offensive security program. Oversees the collection, analysis, assessment, and dissemination information around the latest attack techniques and associated defensive strategies.
  • Sets financial, operational and quality objectives for the unit and develops master operational plans. Plans, develops and manages departmental expense and capital budgets.
  • Develops short- and long-range product and service strategies and plans. Oversees the execution of operating plans for specified area of responsibility.
  • Performs as an idea generator, working with others as a thought leader and subject- matter expert to help brainstorm new processes and solutions. Shares highly complex information related to areas of expertise.
  • Interacts with senior management to keep abreast of objectives. Transfers knowledge and collaborates across functional lines and/or across departments. Interacts with direct reports and peers in management / customers / vendors to interpret information and improve cross-functional processes and programs. Builds and enhances key internal and external contacts.
  • Gains the respect and trust of highly technical staff. Directs through directors and managers who mentor, coach and evaluate their responsive teams and develop employees through on-boarding, open communication, training and development opportunities and performance management processes; builds and maintains employee morale and motivation; ensures the team is appropriately staffed with required competencies; fosters a diverse and inclusive workplace.
About Walgreens
Founded in 1901, Walgreens ( proudly serves nearly 9 million customers and patients each day across its approximately 8,500 stores throughout the U.S. and Puerto Rico. Walgreens has approximately 220,000 team members, including nearly 90,000 healthcare service providers, and is committed to being the first choice for pharmacy, retail and health services, building trusted relationships that create healthier futures for customers, patients, team members and communities.

Basic Qualifications
  • Bachelor’s degree or the equivalent with at least 8 years of experience in IT security.
  • At least 5 years of experience developing and implementing strategic roadmaps, goals and/or objectives.
  • Experience establishing & maintaining relationships with individuals at all levels of the organization, in the business community & with vendors.
  • Experience diagnosing, isolating, and resolving complex issues and recommending and implementing strategies to resolve problems.
  • Experience interacting at the executive level.
  • Experience developing strategic technology initiatives which align with business goals and budget.
  • Experience of driving large scale, enterprise-wide transformation, including the culture and mindset of a group to embrace new and improved ways of using technology.
  • At least 5 years of experience contributing to financial decisions in the workplace.
  • At least 5 years of direct leadership, indirect leadership and/or cross- functional team leadership.
  • Willing to travel up to 20% of the time for business purposes (within state and out of state

Preferred Qualifications
  • Bachelor’s degree in computer science, Engineering, Cybersecurity or related field
  • Certifications in at least one of the following - CISSP, CISM, CISA, CRISC, GPEN, CEH
We will consider employment of qualified applicants with arrest and conviction records.

The Salary below is being provided to promote pay transparency and equal employment opportunities at Walgreens. The actual hourly salary within this range that you will be offered will depend on a variety of factors including geography, skills and abilities, education, experience and other relevant factors. This role will remain open until filled. To review benefits, please click here jobs.walgreens.com/benefits. If you are applying on a job board or unable to click on the link, please copy and paste this URL into your browser jobs.walgreens.com/benefits

Salary Range: $186500 - $320000 / Salaried
Posted 2026-04-30

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