Red Team - Sr Security Engineer

Location: Shawnee Mission

The Red Team – SrSecurity Engineer is responsible for enterprise information security systems and infrastructure platforms for Well Sky. The scope of this job includes information system security administration and maintenance, vulnerability management, and configuration of other security software and solutions.

Key Responsibilities:

Design, scope, and execute red team engagements and adversary emulation exercises against Well Sky systems, cloud environments, and applications, and partner with detection engineering to close the gaps those exercises expose.

Lead the implementation and enhancement of security measures across systems and software development processes, system hardening, monitoring, vulnerability assessment and remediation, incident response, disaster recovery by enforcing secure software development lifecycle practices and considering emerging cybersecurity threats.

Develop and enforce security controls in colocation and cloud environments in strategic alignment with Well Sky policies.

Analyze technical requirements and recommend solutions or enhancements to provide actionable guidance for the business that align with industry standards and regulatory compliance.

Provide technical guidance to development and IT teams by fostering secure software design and deployment.

Participate in the security incident response process by aiding in detection, notification, containment, resolution, and escalation of incidents as needed.

Serve as a subject matter expert for security tools (e.g., SIEM, DLP, EDR, SAST, SCA), optimize configurations and workflows, and provide guidance to other information security teammates and assign tasks as needed.

Leverage AI tools and platforms as an integral part of daily responsibilities to enhance decision-making, streamline workflows, and drive data-informed outcomes.

Perform other job duties as assigned.

Required Qualifications:

 Bachelor's degree in a related field or equivalent work experience 4 - 6 years related work experience At least 2 years of the above experience in an offensive security role: penetration testing, red teaming, adversary emulation, or purple team Hands-on experience executing the full attack lifecycle - reconnaissance, initial access, privilege escalation, lateral movement, persistence, and exfiltration - against enterprise networks, cloud environments, and web applications

Working knowledge of the MITRE ATT&CK framework for planning engagements and mapping findings to detection coverage

Proficiency with offensive tooling such as Burp Suite, Nmap, Metasploit, Blood Hound, and Impacket, and with at least one command-and-control framework such as Cobalt Strike, Sliver, or Mythic Cloud attack and defense experience in AWS, Azure, or GCP, including IAM abuse paths, misconfiguration exploitation, and cloud-native logging and controls

Demonstrated ability to communicate findings to both engineering teams and executives, including business risk, exploitability, and prioritized remediation guidance

Demonstrated daily use of AI assistants and agentic coding tools such as Claude Code, Git Hub Copilot, or Cursor to accelerate research, tooling development, log analysis, and reporting

Practical prompt engineering skill, including decomposing security tasks for large language models and critically validating AI-generated output before acting on it Understanding of the security and privacy risks introduced by AI tooling, including safe handling of PHI and other sensitive data in prompts and adherence to responsible-use policies

Preferred Qualifications:

    Offensive depth

Detection engineering and purple team collaboration, including writing or tuning SIEM detections based on emulated adversary behavior

Malware analysis, reverse engineering, or custom…