Senior Red Team Engineer

At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection. 

Job Description

As a Senior Red Team Engineer, you will plan and lead stealthy, objective‑based adversary emulation across enterprise and cloud environments to validate our defenses against real‑world threats. You will shape the red team’s strategy and roadmap, partner closely with detection engineering/IR (purple teaming), mentor operators, and translate technical risk into clear, actionable recommendations for senior leadership.

What You’ll Do 

• Lead full-scope red team operations, from scoping to exfil.  Including stealthy, multi-stage attack simulations across enterprise environments while staying within rules of engagement. 

• Design advanced adversary emulation scenarios based on threat intelligence and MITRE ATT&CK techniques. 

• Operate in complex enterprise stacks and conduct exploitation of systems, networks, Active Directory, and cloud infrastructure, focusing on realistic threat behavior. 

• Identify gaps in detection, prevention, and response mechanisms, and collaborate with security engineering and detection teams to address them. 

• Build custom tooling and payloads to evade controls and simulate advanced threat capabilities. 

• Manage infrastructure necessary to conduct red team operations. 

• Mentor other red teamers and contribute to internal training, tool development, and process improvement. 

• Develop detailed reports and present findings to both technical and executive stakeholders, translating risk into actionable recommendations. 

What You’ll Bring (Minimum Qualifications) 

• 6+ years of hands-on experience in offensive security, with at least 2 years leading or co-leading objective-based red team operations. 

• Deep understanding of enterprise environments (Windows, Linux, AD, Azure/AWS/GCP), including common misconfigurations and attack paths. 

• Advanced proficiency with offensive tools and frameworks (e.g., Cobalt Strike, Mythic, BloodHound, SharpHound, Mimikatz, PowerShell Empire) and ability to write or modify tooling for OPSEC and EDR evasion. 

• Strong ability to develop or customize attack tooling (Python, PowerShell, C#, Bash). 

• Understanding of modern security controls (EDR, MFA, network segmentation, logging). 

• Expert use of the MITRE ATT&CK framework for planning, execution, and reporting. 

• Excellent communication skills, including the ability to write clear, concise, and technically deep reports and exec-level narratives that drive decisions and remediation. 

 

Preferred Qualifications 

• Contributions to the security community (research, tools, talks, blogs). 

• Relevant certifications (e.g., OSEP, OSCP, CRTO, OSCE, GXPN) are valued but not required.