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At R1, we’re transforming how healthcare works by combining nearly two decades of revenue cycle expertise with advanced technology, including analytics, AI, intelligent automation and workflow orchestration. We pair that technology with the irreplaceable expertise of our people to help hospitals, health systems and medical groups improve financial performance, simplify administrative complexity and create better experiences for patients and providers.
All Together Better defines our culture and the way we work. We’re a diverse, global team united by a shared mission to make healthcare work better for all. Across technology, operations and support functions, our people bring deep expertise, empathy and ingenuity to the work we do. Here, collaboration fuels progress, adaptability sparks innovation and every voice can help shape what’s next for R1 and the future of healthcare.
About the Role
The Offensive Security team is hiring a Senior IT Security Engineer to strengthen how we find and fix vulnerabilities before attackers do. You'll run hands-on penetration tests across infrastructure, networks, and applications, work across multiple cloud environments, and help mature testing methodology and tooling for a healthcare technology company operating at real scale. This is an individual contributor role with room to shape process, not just execute against a checklist.
Responsibilities
Plan and execute penetration tests across internal and external infrastructure, networks, and web and mobile applications.
Perform application security testing — manual and tool-assisted — integrated into the SDLC, including source-code-assisted ("gray box") testing where applicable.
Test across multiple cloud environments (AWS, Azure, and/or GCP), including cloud configuration, IAM, and workload-level exposures.
Simulate real-world adversary techniques against production and pre-production systems, in coordination with engineering and infrastructure owners.
Build, maintain, and extend a toolkit spanning both open-source and commercial tooling; write custom scripts and tools to close gaps in existing coverage.
Document findings with clear risk ratings, reproduction steps, and remediation guidance, for both engineering teams and executive stakeholders.
Partner with engineering, infrastructure, and product teams to validate fixes and reduce time-to-remediation.
Support testing tied to compliance obligations, including HIPAA, SOC 2, and PCI DSS assessments and audits.
Track emerging attack techniques, exploits, and threat intelligence relevant to healthcare and revenue cycle technology environments.
Contribute to tabletop exercises, purple-team collaboration, and internal security training as needed.
Minimum Qualifications
5+ years of hands-on experience in penetration testing or offensive security, spanning both infrastructure/network and application security testing.
At least one recognized offensive security certification — e.g., OSCP, GPEN, GWAPT, GXPN, CEH, or equivalent demonstrated hands-on skill — with a track record of pursuing further certification.
Practical experience testing in multiple cloud environments (AWS, Azure, and/or GCP), not just on-prem infrastructure.
Working knowledge of established methodologies and frameworks: MITRE ATT&CK, the OWASP Testing Guide, and PTES.
Fluency with both open-source and commercial security tooling (e.g., Burp Suite, Zap, Nmap, Metasploit, BloodHound, Nuclei, OWASP ZAP) and the judgment to pick the right tool for the job.
Scripting or automation ability (Python, PowerShell, or Bash) to build custom tooling and speed up repeatable testing.
Experience operating in environments subject to HIPAA, SOC 2, and/or PCI DSS.
Strong written and verbal communication — you can explain a finding's real-world impact to an engineer and to a non-technical stakeholder in the same afternoon.
Comfort operating independently inside a large, fast-paced, matrixed organization.
Preferred Qualifications
Advanced certifications: OSWE, OSCE/OSEE, GXPN, CISSP, or CCSP.
Experience testing containerized environments and Kubernetes.
API security testing experience (REST/GraphQL), beyond standard web app testing.
Familiarity with CI/CD pipeline security and secure SDLC integration.
Experience contributing to or maintaining open-source security tools.
Healthcare, healthcare IT, or financial services industry experience.
Experience with AI models, harnesses, and exploiting AI services.
For this US-based position, the base pay range is $50,640.00 - $137,481.25 per year . Individual pay is determined by role, level, location, job-related skills, experience, and relevant education or training.This job is eligible to participate in our annual bonus plan at a target of 10.00% The healthcare system is always evolving — and it’s up to us to use our shared expertise to find new solutions that can keep up. On our growing team you’ll find the opportunity to constantly learn, collaborate across groups and explore new paths for your career.
Our associates are given the chance to contribute, think boldly and create meaningful work that makes a difference in the communities we serve around the world. We go beyond expectations in everything we do. Not only does that drive customer success and improve patient care, but that same enthusiasm is applied to giving back to the community and taking care of our team — including offering a competitive benefits package.
R1 RCM Inc. (“the Company”) is dedicated to the fundamentals of equal employment opportunity. The Company’s employment practices , including those regarding recruitment, hiring, assignment, promotion, compensation, benefits, training, discipline, and termination shall not be based on any person’s age, color, national origin, citizenship status, physical or mental disability, medical condition, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status or any other characteristic protected by federal, state or local law. Furthermore, the Company is dedicated to providing a workplace free from harassment based on any of the foregoing protected categories.
If you have a disability and require a reasonable accommodation to complete any part of the job application process, please contact us at 312-496-7709 for assistance.
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