Senior Cyber Security Engineer

Direct Supply, Inc.; Milwaukee (WI); On-site; USD 120,000 - 160,000; Full time

Job summary

Direct Supply, Inc. is seeking a Senior Cyber Security Engineer to own vulnerability management and lead penetration testing across its technology environments. You will collaborate with engineering, operations and security teams to drive remediation, improve processes and strengthen security controls.

The role reports to the Director of Information Security and requires hands-on technical expertise with a focus on reducing exposure and delivering measurable improvements in security posture.

Qualifications

• 6+ years of progressive experience in information security or security engineering.

Responsibilities

• Own vulnerability management operations across infrastructure, cloud and applications.
• Analyze and prioritize security vulnerabilities by validating findings and assessing exploitability and business impact.
• Drive remediation by coordinating actions with engineering and operations teams.
• Automate scanning, ticketing and reporting workflows to improve efficiency.
• Plan and execute internal and external penetration testing and validate findings.
• Coordinate external penetration testing services and ensure coverage and quality.
• Retest fixes to confirm vulnerabilities are addressed.
• Analyze root causes and recommend practical security improvements.

Skills

Vulnerability management

Penetration testing

Security scanning platforms

Risk-based prioritization

Automation of security workflows

Security metrics reporting

Cloud and on-prem infrastructure

Education

Bachelor's degree in Computer Science or related field

Tools

Security platforms

Vulnerability scanning tools

Penetration testing tools

Job description

Senior Cyber Security Engineer Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. The Senior Cyber Security Engineer plays a critical role in identifying, assessing and reducing cybersecurity risks across Direct Supply’s technology environments. This role provides hands-on technical expertise and operational ownership of vulnerability management and penetration testing to strengthen security controls, reduce exposure and protect business systems and information. Reporting to the Director of Information Security, you’ll work independently and collaborate with engineering, operations and security teams to drive effective remediation, improve security processes and deliver measurable improvements in Direct Supply’s security posture.

What You’ll Do and Impact:

• Own vulnerability management operations by establishing effective processes, maintaining security scanning tools and ensuring reliable coverage across infrastructure, cloud and application environments to identify and reduce security exposure.
• Analyze and prioritize security vulnerabilities by validating findings and assessing exploitability, asset criticality and business impact to focus remediation efforts on the highest risks.
• Drive vulnerability remediation by partnering with engineering and operations teams to coordinate corrective actions, monitor progress, verify fixes and escalation unresolved risks.
• Improve security processes by automating scanning, ticketing and reporting workflows to increase efficiency, strengthen consistency and reduce manual effort.
• Monitor and report security performance through metrics on scanning coverage, remediation progress, overdue vulnerabilities and recurring risks to improve visibility and support informed decisions.
• Plan and execute internal and external penetration testing by defining assessment scope, conducting security testing and identifying exploitable weaknesses to strengthen security defenses.
• Validate security weaknesses and potential attack paths through automated discovery, manual testing and controlled exploitation to assess business impact and deliver actionable findings.
• Coordinate external penetration testing services by managing testing scope, schedules, access and deliverables while monitoring provider performance to ensure effective testing coverage and quality.
• Drive resolution of penetration testing findings by validating results, providing remediation guidance, coordinating corrective actions and retesting fixes to confirm vulnerabilities have been addressed.
• Strengthen security practices by analyzing root causes, recommending improvements to system designs and configurations, and sharing technical knowledge to prevent recurring vulnerabilities.

What You'll Bring:

• Bachelor's degree in Computer Science, Engineering, Information Security or a related field.
• 6+ years of progressive experience in information security or security engineering, including hands-on experience in vulnerability management and penetration testing.
• Demonstrated expertise in vulnerability assessment, security scanning platforms, asset coverage, finding validation and risk-based prioritization to identify and reduce security exposure.
• Hands-on experience conducting internal and external penetration testing, including manual validation, controlled exploitation, security risk assessment and technical reporting.
• Experience operating, configuring and troubleshooting security platforms and automating security workflows to improve operational efficiency and testing effectiveness.
• Experience assessing vulnerabilities and security risks across infrastructure, cloud and application environments, including complex cloud environments.
• Ability to independently investigate complex security issues, identify root causes and recommend practical corrective actions that reduce recurring risks.
• Experience coordinating external security testing providers and communicating technical findings, remediation priorities and security risks to technical stakeholders and leadership.
• OSCP, GPEN, GWAPT or relevant vulnerability management certifications; scripting and API integration experience; and experience testing web applications, APIs and cloud environments preferred.

Job to be performed in the location listed.

Generous benefit package available.

© 2013 to 2026 Direct Supply, Inc. All rights reserved.

Direct Supply delivers solution-driven platforms, products and services to help solve the toughest challenges facing Senior Living and Healthcare.

For more than 35 years, we’ve grown consistently while expanding our offering of innovative solutions for virtually every critical area of senior health across the continuum of care.

If you asked our 1,200+ Partners what separates Direct Supply from other applied technology companies, it’s that we are 100% employee owned and driven to work with a purpose.

Every day, we strive to honor our mission of enhancing the lives of millions of seniors and healthcare professionals in a results-oriented agile environment that gives our Partners the necessary tools and flexibility to truly bring what’s next to Healthcare.

Ready to make a difference?