Senior Cyber Security Engineer

Direct Supply; Wisconsin; On-site; USD 120,000 - 170,000; Full time

Benefits offered by this job

Generous benefit package

Job summary

Direct Supply is seeking a Senior Cyber Security Engineer to own vulnerability management and penetration testing across infrastructure, cloud, and applications. You will drive remediation with engineering and operations teams, automate workflows, and monitor security performance to improve posture.

The role requires 6+ years in information security, hands-on testing experience, and the ability to coordinate external testers while communicating risks to leadership.

Qualifications

• Bachelor's degree in CS, Engineering, Information Security or related field.
• 6+ years of progressive information security or security engineering experience.
• Experience in vulnerability assessment and risk-based prioritization.
• Hands-on internal and external penetration testing experience.
• Experience automating security workflows and operating security platforms.
• Experience assessing vulnerabilities across infrastructure, cloud and apps.
• Ability to investigate complex security issues and propose corrective actions.
• Experience coordinating external security testers and communicating findings.
• Certifications such as OSCP, GPEN, GWAPT preferred; scripting & API integration experience.

Responsibilities

• Own vulnerability management operations across infra, cloud and apps.
• Analyze and prioritize vulnerabilities based on risk.
• Drive remediation with engineering and operations teams.
• Automate scanning, ticketing and reporting workflows.
• Monitor and report security performance with metrics.
• Plan and execute internal and external penetration testing.
• Validate weaknesses and attack paths; deliver actionable findings.
• Coordinate external testing services and ensure coverage.
• Drive resolution of findings and retest fixes.
• Share knowledge to strengthen security practices.

Skills

Vulnerability management

Penetration testing

Security assessment

Security automation

Cloud security

Root cause analysis

Documentation & reporting

External testing coordination

Scripting & API integration

Web apps testing

Education

Bachelor's degree in Computer Science or related field

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 esc? Wait keep: "escalate 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.

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