Senior Red Team Security Engineer - Offensive & Cloud

WellSky Corporation; United States; On-site; USD 150,000 - 210,000; Full time

Benefits offered by this job

Excellent benefits package

401(k) with match

Generous paid time off

Educational assistance

Job summary

WellSky seeks a Sr Security Engineer to own red team engagements across enterprise systems, cloud environments, and applications, partnering with detection engineering to close the gaps those exercises expose.

You will lead offensive assessments, implement secure coding practices, advise development and IT teams, and leverage AI tools to accelerate research, tooling development, and reporting.

Qualifications

• Bachelor's degree in a related field or equivalent work experience.
• 4 - 6 years related work experience.
• At least 2 years in an offensive security role: penetration testing, red teaming, adversary emulation, or purple team.
• Hands-on experience executing the full attack lifecycle against enterprise networks, cloud environments, and web applications.
• Working knowledge of MITRE ATT&CK framework for planning engagements and mapping findings to detection coverage.
• Proficiency with offensive tooling such as Burp Suite, Nmap, Metasploit, BloodHound, and Impacket, and with at least one C2 framework (Cobalt Strike, Sliver, Mythic).
• Cloud attack and defense experience in AWS, Azure, or GCP, including IAM abuse paths and cloud-native logging and controls.
• Ability to communicate findings to engineers and executives with risk, exploitability, and remediation guidance.
• Experience using AI assistants for research, tooling, log analysis, and reporting.
• Prompt engineering skills for large language models and AI safety considerations.
• Knowledge of AI risk, PHI handling, and responsible-use policies.

Responsibilities

• Design, scope, and execute red team engagements and adversary emulation against WellSky systems, cloud environments, and applications.
• Lead the implementation and enhancement of security measures across systems and software development processes, including hardening and incident response.
• Develop and enforce security controls in colocation and cloud environments aligned with WellSky policies.
• Analyze requirements and provide solutions aligned with industry standards and regulatory compliance.
• Provide technical guidance to development and IT teams for secure design and deployment.
• Participate in security incident response and escalation as needed.
• Serve as SME for security tools and optimize configurations and workflows.
• Leverage AI tools to enhance decision-making and reporting.

Skills

Red Team engagements/ adversary emul

MITRE ATT&CK

Offensive tooling

Cloud security

AI tools & prompts

Communication to execs

Security tooling (SIEM, EDR, SAST)

Education

Bachelor's degree or equivalent

Tools

Burp Suite

Nmap

Metasploit

BloodHound

Impacket

Cobalt Strike/ Sliver/ Mythic

Job description

WellSky seeks a Sr Security Engineer to own red team engagements across enterprise systems, cloud environments, and applications, partnering with detection engineering to close the gaps those exercises expose.

You will lead offensive assessments, implement secure coding practices, advise development and IT teams, and leverage AI tools to accelerate research, tooling development, and reporting.