Red Team - Sr Security Engineer

The Red Team – SrSecurity Engineer is responsible for enterprise information security systems and infrastructure platforms for WellSky. 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 WellSky 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 WellSky 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 teamHands-on experience executing the full attack lifecycle - reconnaissance, initial access, privilege escalation, lateral movement, persistence, and exfiltration - against enterprise networks, cloud environments, and web applicationsWorking knowledge of the MITRE ATT&CK framework for planning engagements and mapping findings to detection coverageProficiency with offensive tooling such as Burp Suite, Nmap, Metasploit, BloodHound, and Impacket, and with at least one command-and-control framework such as Cobalt Strike, Sliver, or MythicCloud attack and defense experience in AWS, Azure, or GCP, including IAM abuse paths, misconfiguration exploitation, and cloud-native logging and controlsDemonstrated ability to communicate findings to both engineering teams and executives, including business risk, exploitability, and prioritized remediation guidanceDemonstrated daily use of AI assistants and agentic coding tools such as Claude Code, GitHub Copilot, or Cursor to accelerate research, tooling development, log analysis, and reportingPractical prompt engineering skill, including decomposing security tasks for large language models and critically validating AI-generated output before acting on itUnderstanding 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 policiesPreferred Qualifications:    Offensive depthDetection engineering and purple team collaboration, including writing or tuning SIEM detections based on emulated adversary behaviorMalware analysis, reverse engineering, or custom payload development and EDR evasion in an authorized testing contextActive Directory and Microsoft Entra ID attack path analysis and hardeningContainer and Kubernetes security testing, and CI/CD pipeline or software supply chain attack techniquesApplication security depth, including SAST, DAST, and SCA triage, secure code review, and threat modelingContributions to the security community such as open-source tooling, CVE research, CTF placement, conference talks, or published researchScripting and automation ability in Python, PowerShell, Bash, or Go to build tooling and automate repetitive testingAI and machine learning securityExperience testing AI and LLM-enabled applications for prompt injection, jailbreaks, insecure output handling, data leakage, and agent or tool-abuse pathsFamiliarity with the OWASP Top 10 for LLM Applications, MITRE ATLAS, and the NIST AI Risk Management FrameworkExperience building AI-assisted security automation, such as agents or scripts for alert triage, recon enrichment, log correlation, or evidence collectionUnderstanding of how to secure AI infrastructure, including model endpoints, MCP servers and tool integrations, RAG data stores, and API key management for AI servicesExperience evaluating third-party AI tools for enterprise risk and defining safe-use guardrailsCertifications, any of the followingOffensive security: OSCP, OSEP, OSWE, CRTO, GPEN, GXPN, or PNPTCloud: AWS, Azure, or GCP security specialty certificationGeneral: CISSP, GCIH, or GCIAHealthcare and complianceHealthcare industry experienceWorking knowledge of the HIPAA Security Rule, HITRUST CSF, SOC 2, and NIST 800-53 or the NIST Cybersecurity Framework, and how they constrain offensive testing scope and evidence handlingExperience conducting authorized testing in regulated environments under formal rules of engagement and change-control processesJob Expectations:Willing to work additional or irregular hours as neededMust work in accordance with applicable security policies and procedures to safeguard company and client informationMust be able to sit and view a computer screen for extended periods of time#LI-TC1#LI-OnsiteWellSky is where independent thinking and collaboration come together to create an authentic culture. We thrive on innovation, inclusiveness, and cohesive perspectives. At WellSky you can make a difference.Here are some of the exciting benefits full-time teammates are eligible to receive at WellSky:Excellent medical with Rx, dental, and vision benefitsMental Health support through EAPGenerous paid time off, plus 13 paid holidays100% vested 401(K) retirement plansEducational assistance up to $2500 per yearWellSky provides equal employment opportunities to all people without regard to race, color, national origin, ancestry, citizenship, age, religion, gender, sex, sexual orientation, gender identity, gender expression, marital status, pregnancy, physical or mental disability, protected medical condition, genetic information, military service, veteran status, or any other status or characteristic protected by law. WellSky is proud to be a drug-free workplace.Applicants for U.S.-based positions with WellSky must be legally authorized to work in the United States. Verification of employment eligibility will be required at the time of hire. Certain client-facing positions may be required to comply with applicable requirements, such as immunizations and occupational health mandates.Data Privacy Notice for Job Applicants and TeammatesSummaryLocation: Overland Park, KSType: Full time