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Weekend Offensive Security Engineer Jobs in Illinois

AWAE, OSCP, OSCE, OSEE offensive security certifications * Significant development and engineering backgrounds * Cloud Service penetration testing tradecraft and methodologies across multiple service ...

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Security Crowd Manager Part-time / Evening and weekends availability required   Multiple venue ... piercings, and facial or offensive tattoos are not allowed Additional information:   ...

Security Crowd Manager Part-time / Evening and weekends availability required   Multiple venue ... piercings, and facial or offensive tattoos are not allowed Additional information:   ...

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Weekend Offensive Security Engineer information

What is the difference between Weekend Offensive Security Engineer vs Penetration Tester?

AspectWeekend Offensive Security EngineerPenetration Tester
CertificationsOSCP, CEH, GPENOSCP, CEH, GPEN
Work EnvironmentPart-time, project-based, often remoteFull-time, consulting or in-house roles
Industry UsageSecurity firms, tech companies, freelanceSecurity firms, consulting, internal security teams

The Weekend Offensive Security Engineer and Penetration Tester roles share similar certifications and skills, focusing on identifying vulnerabilities. However, the Weekend Offensive Security Engineer typically works part-time or on a flexible schedule, often remotely, while Penetration Testers usually hold full-time positions. Both roles are vital in cybersecurity, but the engineer role emphasizes a flexible, project-based approach, whereas Penetration Testers often work within organizations or consulting firms on scheduled assessments.

What are the most commonly searched types of Offensive Security Engineer jobs in Illinois? The most popular types of Offensive Security Engineer jobs in Illinois are:
What job categories do people searching Weekend Offensive Security Engineer jobs in Illinois look for? The top searched job categories for Weekend Offensive Security Engineer jobs in Illinois are:
What cities in Illinois are hiring for Weekend Offensive Security Engineer jobs? Cities in Illinois with the most Weekend Offensive Security Engineer job openings:
Infographic showing various Weekend Offensive Security Engineer job openings in Illinois as of August 2026, with employment types broken down into 84% Full Time, 13% Part Time, and 3% Contract. Highlights an 92% Physical, 3% Hybrid, and 5% Remote job distribution.

Senior Consultant, AI Application Security

Medium

Chicago, IL • On-site

$85.56 - $176.38/hr

Other

Posted 3 days ago

New


Job description

About Coalfire

Coalfire is on a mission to make the world a safer place by solving our clients’ hardest cybersecurity challenges. We work at the cutting edge of technology to advise, assess, automate, and ultimately help companies navigate the ever-changing cybersecurity landscape. We are headquartered in Chicago, Illinois with offices across the U.S. and U.K., and we support clients around the world.

But that’s not who we are – that’s just what we do.

We are thought leaders, consultants, and cybersecurity experts, but above all else, we are a team of passionate problem‑solvers who are hungry to learn, grow, and make a difference.

Position Summary

The Senior Consultant works closely with Project Managers, Delivery Directors, and other Delivery team members to lead engagements, assessing the security of various types of client applications and supporting infrastructure against security best practices. The Senior Consultant is a technical leader with broad technical skills, meeting the objectives of their engagements, collaborating with clients, mentoring teammates, and providing subject matter expertise across one or more technical domains. The Senior Consultant is a trusted advisor to clients, and through objective testing and results reporting, supports the client in making well‑informed, risk‑based decisions to improve overall security posture.

What You’ll Do
  • Working independently and collaboratively with a team to both lead and support
  • Perform penetration testing on applications with complex technology stacks from both a:
    • Blackbox perspective
    • Whitebox perspective
  • Dynamically flex your skills when assessing emerging or custom technologies.
  • Contextualize vulnerabilities and assess realistic impact to a client accounting for mitigating and aggravating factors.
  • Manage priorities and tasks to achieve utilization targets.
  • Operate with professionalism both internally and with clients.
  • Ensure quality reports and services are delivered efficiently and on time.
  • Maintains strong depth of knowledge in the practice area.
  • Collaborate with project managers, quality management, sales and other delivery team members to drive customer satisfaction and meet project deliverables.
What You’ll Bring
  • Application penetration testing and assessment tradecraft and methodologies (including browser‑based, API, and AI Penetration testing)
  • Working knowledge of at least two programming or scripting languages
  • Strong understanding of security principles and industry best practices.
  • Minimum of 4 years’ experience in a consulting/professional services role
  • Minimum of 4 years’ experience in Application Security and/or Software Development
  • Strong consulting skills including:
    • Time management, performing adjacent tasks while ensuring on‑time delivery, escalating issues as needed
    • Verbal communication, leading client calls for project kickoffs and debrief
    • Written communication
    • Report writing, for both executive audiences and technical staff
  • Required proficiency in:
    • Web Application Penetration Testing
    • AI Penetration Testing
  • Strong overall technical skills, with additional strong expertise in at least one of the following preferred:
    • Mobile Application Penetration Testing
    • Thick Application Penetration Testing
    • Hardware Penetration Testing
    • Secure Code Review
    • Container Penetration Testing
    • Cloud Penetration Testing
    • Network Active Directory Penetration Testing
Bonus Points
  • UK CREST Certification and eligibility to be approved for and maintain UK SC level Clearance
  • Strongly preferred CREST Certifications
  • CREST Practitioner Security Analyst (CPSA)
  • CREST Practitioner Threat Intelligence Analyst (CPTIA)
    • AWAE, OSCP, OSCE, OSEE offensive security certifications
    • Significant development and engineering backgrounds
    • Cloud Service penetration testing tradecraft and methodologies across multiple service providers (e.g. AWS, GCP, etc.).
    • Mobile platform and application penetration testing tradecraft and methodologies across both iOS and Android.
    • Red/Purple Team tradecraft and methodologies.
    • Social engineering in all its forms.
  • AWS Certified Solutions Architect – Professional, AWS Certified Security, AWS Certified Advanced Networking, AWS Certified SysOps Administrator
  • Network, Database, System administration experience and certifications
Compensation

£65,000 - £134,000 a year

The salary range listed is a reasonable estimate of the compensation range for this role based on national salary averages. The actual salary offer to the successful candidate will be based on job‑related education, geographic location, training, licensure and certifications and other factors. You may also be eligible to participate in annual incentive, commission, and/or recognition programs.

Why You’ll Want to Join Us

At Coalfire, you’ll find the support you need to thrive personally and professionally. In many cases, we provide a flexible work model that empowers you to choose when and where you’ll work most effectively – whether you’re at home or an office.

Regardless of location, you’ll experience a company that prioritizes connection and wellbeing and be part of a team where people care about each other and our communities. You’ll have opportunities to join employee resource groups, participate in in‑person and virtual events, and more. And you’ll enjoy competitive perks and benefits to support you and your family, like paid parental leave, flexible time off, certification and training reimbursement, digital mental health and wellbeing support membership, and comprehensive insurance options.

At Coalfire, equal opportunity and pay equity is integral to the way we do business. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. Coalfire is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. To request reasonable accommodation to participate in the job application or interview process, our Human Resources team at HumanResourcesMB@coalfire.com.

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