Join Rightway as the first Senior Security Systems Administrator, where you will play a critical role in designing and implementing innovative security and IT controls and strategies. Your work will have high visibility and impact at a rapidly growing organization, and you will wear many hats in furtherance of Security, IT, and broader organizational objectives. We deeply believe in mentorship and learning from each other, so you can expect to both guide and be guided on your journey with us!


  • Spearhead the expansion of our Identity and Access Management (IAM) platform (Okta) implementing role-based access control (RBAC), and cutting-edge authentication mechanisms (e.g., YubiKey, PassKeys), from inception to successful adoption. 
  • Create, tune, investigate, triage, and remediate security alerts from multiple sources including Next Generation Antivirus (Crowdstrike), Mobile Device Manager (JAMF), Google, Okta, DLP (Nightfall), and the Security Operations Center.
  • Develop and execute Data Loss Prevention (DLP) and Zero Trust strategies, covering endpoints, SaaS applications, and Cloud.
  • Scan, monitor, risk assess, and treat vulnerabilities at the endpoint and in our proprietary SaaS application (i.e., OWASP attack vectors, open source libraries).
  • Administer and monitor, public key infrastructure, certificate issuance, and authentication across Wifi (Cisco Meraki, SecureW2), endpoints, and cloud infrastructure (AWS).
  • Oversee the coordination, execution, and remediation of penetration tests at the network and application level.  
  • Bolster security of third party SaaS applications and MacOS endpoints.  
  • Enhance security operational efficiency through creation and optimization of JIRA workflows in furtherance of IT, Security, and Compliance objectives.


  • 5-10 years of related work experience in a dedicated security role with IT system administration background and/or understanding.
  • Maintains a security certification such as CISSP, SSCP, Security+, etc. 
  • Passionate about security and understands defense in depth strategies across endpoints, cloud networks, SaaS solutions, proprietary applications, and data.  
  • Ability to identify security risks then suggest and drive remediations to completion. 
  • Positive, collaborative, and proactive attitude comfortable working independently in a fast-paced environment.
  • Detailed knowledge of Zero Trust platforms and strategies (e.g., ZScaler, Twingate).
  • Deep understanding of SAML 2.0 SSO and SCIM, and SSO at protocol and implementation levels, both generally and in OKTA environments.  
  • Substantial experience with vulnerability management at the endpoint and SaaS application (OWASP) level.
  • Track record of implementing Role Based Access Control (RBAC) with Okta and HRIS.
  • Operated in one or more regulated environments (e.g., healthcare, finance, education) 
  • Possesses a thorough understanding of network fundamentals.


  • AWS Certifications such as AWS CCP, SSA. 
  • Experience producing evidence for SOC2 or HITRUST audits. 
  • Experience with Auth0, FushionAuth, or similar providers.

BASE SALARY: $125,000 – $175,000


In response to ongoing and industry-wide fraudulent recruitment activities (i.e., job scams), Rightway wants to inform potential candidates that we will only contact them from the @rightwayhealthcare.com email domain. We will never ask for bank details or deposits of any kind as a condition of employment. If you have any questions about a suspicious interaction with Rightway, please feel free to reach out to us at hr@rightwayhealthcare.com.


Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient’s care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them.

Since its founding in 2017, Rightway has raised over $130mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global at a valuation of $1 billion. We’re headquartered in New York City, with a satellite office in Denver. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.


We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members who will:

  • We are human first

Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding. 

  • We redefine what is possible 

We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems.

  • We debate then commit 

We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a “yes, and” mentality, and assume positive intent. Once a decision is made, we align and champion it as one team.

  • We cultivate grit 

Changing healthcare doesn’t happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity.

  • We seek to delight

Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members’ care and take that responsibility seriously. When faced with an obstacle, we are kind, respectful, and solution-oriented in our approach. We hold ourselves accountable to our clients and our members’ success. 

Rightway is a healthcare company looking to improve healthcare outcomes for everyone, everywhere. With that in mind, we have to consider what is good for the health of our team, the company, and the communities we operate in. As such, Rightway has determined a mandatory COVID-19 vaccination policy for all employees, in combination with other safety precautions, is the best way forward.

Rightway is PROUDLY an Equal Opportunity Employer that believes in strength in the diversity of thought processes, beliefs, background and education and fosters an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis covered by appropriate law. All employment is decided on the consideration of merit, qualifications, need and performance.

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