4w
Save
Mark Applied
Hide
Lead, Offensive Security
Louisville or New York City or Dallas or Charlotte or Tampa or Miami or Washington or Chicago or Boston or Atlanta or Nashville
$142k-$196k/yr RemoteFull Time
6+ YOE6+ Mgmt6+ years in red team/penetration testing with leadership experience; production Python engineering; built or operated agentic AI/LLM applications; experience attacking AI/ML systems; production cloud experience (AWS, GCP, or Azure).
Python, PyRIT, Garak, MITRE ATLAS, OWASP Top 10 for LLM Applications, NIST AI Risk Management Framework, AWS, GCP, Azure, Hack The Box Pro Labs
1mo
Save
Mark Applied
Hide
WebApp Offensive Security Engineer
United States or Chicago
$196k-$242k/yr RemoteFull Time
Extensive hands-on web application penetration testing experience, ability to reproduce and validate edge-case exploits, strong communication, proxy tool experience (Burp Suite), scripting (Python), and history of security research or bug bounty contributions.
NodeZero, Burp Suite, Python, Nuclei, sqlmap, LangChain, LangFlow, Postgres, Neo4j, Jira, Model Context Protocol (MCP)
3w
Save
Mark Applied
Hide
X-Day Offensive Research (XOR) Vulnerability Researcher
Jersey City or Washington or Chicago or Plano or Houston or Tampa or Atlanta or Wilmington or McLean or Columbus
$152k-$260k/yr OnsiteFull Time
5+ YOE5+ years cybersecurity experience with vulnerability research, reverse engineering, exploit development, and assessments; strong OS internals and analysis skills; proven CVE track record; excellent communication.
IDA Pro, Ghidra, Binary Ninja, WinDbg, GDB, RR, LibFuzzer, LibAFL, AFL++, OSS-Fuzz, Syzkaller, LLVM, Angr, KLEE, Intel Pin, DynamoRIO, Frida, C/C++, Java, .NET, Open Worldwide Application Security Project (OWASP) Top Ten, National Institute of Standards and Technology (NIST) Cybersecurity Framework
2w
Save
Mark Applied
Hide
Senior Penetration Testing Engineer
Chicago, Illinois, United States
$93k-$144k/yr HybridFull Time
3+ YOEBachelor's in CS/related or 6 years' equivalent; minimum 3 years penetration testing/offensive security; preferred offensive security certifications; strong communication and reporting skills.
3w
Save
Mark Applied
Hide
Senior Red Team Operator
Minneapolis or Atlanta or Cincinnati or Cupertino or Portland or New York or Chicago or Englewood or Charlotte or Irving
$133k-$157k/yr HybridFull Time
8+ YOEBachelor's degree or equivalent, 8+ years in information security with offensive security/Red Team experience; expertise in exploit development, offensive tooling, and scripting; strong communication and leadership.
Cobalt Strike, Metasploit, Mythic, Sliver, Python, PowerShell, C/C++, C#, Go, Shell, EDR, XDR, Infrastructure as Code (IaC)
3w
Save
Mark Applied
Hide
Lead Penetration Test Engineer
Boston or Chicago or Dallas or Houston or Englewood or Raleigh or Princeton or New York or Southfield or Washington or Toronto or Calgary or Boulder
$135k-$200k/yr HybridFull Time
8+ YOEBachelor's degree or equivalent, minimum 8 years information security experience focused on penetration testing, expertise with offensive techniques, cloud/app security, scripting, and at least one offensive security certification.
Burp Suite, Nessus, Metasploit, Nmap, DAST, SAST, SCA, CI/CD, Bash, Python, Go, PowerShell, JavaScript, MITRE ATT&CK, OWASP Top 10, CVE, CVSS, CWE
1d
Save
Mark Applied
Hide
CDL Class A Dedicated
Ann Arbor or Detroit or Fort Wayne or Gary or Indianapolis or Kalamazoo or Lafayette or New Augusta or Traders Point or Michigan or Ohio or Indiana or Illinois or Missouri or Kansas
$1k-$2k/wk FieldFull Time
1+ YOE12 months recent tractor-trailer experience, limits on accidents/tickets and job changes, no serious offenses; CDL Class A required.
2mo
Save
Mark Applied
Hide
Security Engineer
Chicago, Illinois, United States
$145k-$195k/yr OnsiteFull Time
4+ YOE4+ years in security engineering or DevSecOps; hands-on offensive and defensive security; SIEM; code experience in TS/Node; vulnerability management; AI-native tooling.
Datadog, Splunk, Elastic, Panther, TypeScript, Node.js, Rust, Go, Python, Claude Security, Claude Code, SAST, DAST, CI/CD
1w
Save
Mark Applied
Hide
CDL A OTR Owner Operator Truck Driver
Austin or Centerville or Chicago or Dallas or Dessau or Houston or Jacksonville or Orlando or San Antonio or Tallahassee or Waco or Canada
$75k-$90k/yr FieldContract
1+ YOECDL A driver with ≥1 year tractor‑trailer experience, ≤3 moving violations in 5 years, no DOT‑defined accidents or serious offenses in 5 years.
1w
Save
Mark Applied
Hide
CDL A Owner Operator - Home Daily
Channahon or Chicago
$4k-$5k/wk FieldContract
1+ YOEClass A CDL, 1 year tractor-trailer experience, ≤1 preventable accident in 3 years, no serious offenses in 5 years; hazmat endorsement reimbursed.
3mo
Save
Mark Applied
Hide
Sr. Info Security Specialist
Chicago, Illinois, United States
$122k-$157k/yr OnsiteFull Time
5+ YOE5+ years red teaming or offensive security; bachelor’s degree or equivalent; strong attacker tradecraft; hands-on in endpoint, identity, cloud; knowledge of EDR, SIEM; purple team; communications.
Python, PowerShell, Bash, EDR, SIEM, Cloud security tools, Threat modeling tools
3w
Save
Mark Applied
Hide
Lead Penetration Test Engineer
Princeton or Boston or Chicago or Dallas or Houston or Englewood or Raleigh or New York or Southfield or Washington or Toronto or Calgary
$135k-$200k/yr HybridFull Time
8+ YOEBachelor's or equivalent, 8+ years in information security with penetration testing focus; hands-on with Burp Suite, Nessus, Metasploit, Nmap; scripting (Bash, Python, Go, PowerShell, JavaScript); offensive cert (OSCP or similar).
Burp Suite, Nessus, Metasploit, Nmap, MITRE ATT&CK, OWASP Top 10, DAST, SAST, SCA, CVE, CVSS, CWE, Bash, Python, Go, PowerShell, JavaScript, CI/CD
1w
Save
Mark Applied
Hide
CDL-A OTR Dry Van Truck Driver
Charlotte or Chicago or Dallas or Des Moines or Jersey City
$88k-$104k/yr FieldFull Time
2+ YOEMust be 23+, hold a current Class A CDL, have 2 years verifiable semi-truck experience, meet DOT physical/drug screen, have limited moving violations and no recent major offenses.
ELD
3w
Save
Mark Applied
Hide
Forward deployed engineer Chicago
Chicago, Illinois, United States
FieldFull Time
Strong infrastructure and networking fundamentals (Docker, DNS, TLS), Linux debugging, ability to read Go/TypeScript/Python, familiarity with enterprise networks, basic offensive security knowledge, strong communication; must live in Chicago.
Docker, Postgres, Go, TypeScript, Python, Linux, AWS, Azure, GCP, SSO, IdP, PKI, DNS, TLS
1mo
Save
Mark Applied
Hide
Principal Red Team Operator
Johnston or Boston or Iselin or Pittsburgh or Cleveland or Chicago or Philadelphia or Manchester
$120k-$210k/yr HybridFull Time
4+ YOE4+ years hands-on offensive security experience with red/purple team operations, adversary emulation, campaign-based testing; Bachelor's preferred or equivalent experience; OSCP/OSEP/CRTO/CRTP or similar; AI security exposure; strong communication.
3w
Save
Mark Applied
Hide
Associate Principal, Adversarial Red Team
Chicago, Illinois, United States
$122k-$197k/yr HybridFull Time
5+ YOE5+ years in cybersecurity with 3+ years penetration testing; strong offensive security skills (OSINT, red team, C2, evasion), programming/scripting, cloud testing (AWS/Azure), EM/EDR familiarity, excellent communication, and security certifications preferred.
AI/LLM, Model Context Protocol (MCP), AWS, Azure, Crowdstrike, Carbon Black, Kali, Armitage, Metasploit, Cobalt Strike, Nighthawk, Nmap, Qualys, Nessus, Burp Suite, Wireshark, Recon-NG, Ettercap, Bettercap, Hashcat, Bloodhound, Ida Pro, Ghidra, Sublist3r, Rubeus, Mimikatz, CrackMapExec, Exploitdb, Yersinia, Impacket, MSSQL, DB2, MySQL, Microsoft Word, Microsoft Excel, Microsoft PowerPoint, Microsoft Visio, Microsoft SharePoint, ServiceNow, DMS, PolicyTech
1mo
Save
Mark Applied
Hide
Cyber Purple Team Operator
Chicago or Tempe
$100k-$169k/yr HybridFull Time
3+ YOE3+ years in cybersecurity with purple/red/blue teaming experience; strong MITRE ATT&CK knowledge; coding/scripting (Python/PowerShell/Bash); SIEM/EDR; cloud security; offensive security tools; AI automation; cloud environments; AD/EntraID; OSI/networking concepts; EDR evasion payloads; relevant certifications.
Cobalt Strike, Metasploit, Caldera, Mythic, Breach and Attack Simulation, Python, PowerShell, Bash, Azure, AWS, EntraID, Active Directory, EDR, SIEM
Explore Jobs
Expand Your Job Search
Top Cities Near Chicago for Offensive
- Offensive jobs in Aurora, IL
- Offensive jobs in Joliet, IL
- Offensive jobs in Naperville, IL
- Offensive jobs in Elgin, IL
- Offensive jobs in Waukegan, IL
- Offensive jobs in Cicero, IL
- Offensive jobs in Hammond, IN
- Offensive jobs in Gary, IN
- Offensive jobs in Arlington Heights, IL
- Offensive jobs in Evanston, IL
- Offensive jobs in Schaumburg, IL
- Offensive jobs in Bolingbrook, IL
- Offensive jobs in Palatine, IL
- Offensive jobs in Skokie, IL
- Offensive jobs in Des Plaines, IL
- Offensive jobs in Orland Park, IL
- Offensive jobs in Tinley Park, IL
- Offensive jobs in Oak Lawn, IL
- Offensive jobs in Berwyn, IL
- Offensive jobs in Mount Prospect, IL