ABOUT THE ROLE:
We're hiring a Senior Manager, Infrastructure to lead the team that builds and runs the platform underneath every Rightway product. Our platform runs on AWS and Amazon EKS, defined in Terraform and Helm, deployed through Bitbucket Pipelines and Argo CD, and it handles protected health information for employers, health plans, and their members.
This is a player coach role. You will manage a small team of infrastructure engineers, own their backlog and delivery commitments, and work with security, compliance, data, and product engineering leaders to set priorities. You will also be one of the strongest engineers on the team, writing infrastructure code and owning the platform end to end.
We're an AI-native engineering team that uses AI tooling daily in our development workflow, and we expect our leaders to model that, establish best practices, and help their teams get better at working with these tools.
WHAT YOU’LL DO:
- Manage, coach, and grow a team of infrastructure engineers
- Own the infrastructure backlog: intake, prioritization, sequencing, and delivery commitments
- Partner with security, compliance, data, and product engineering to set priorities and make tradeoffs visible
- Own our AWS environment, EKS clusters, and GitOps deployment with Argo CD
- Write and review Terraform, Helm, and pipeline code, especially on the highest risk work
- Own the CI/CD platform that builds, tests, and promotes every service to production
- Own the managed data tier with the teams who use it, including Postgres, Redis, Kafka, and our warehouse infrastructure
- Build security and compliance controls into the platform, and support HITRUST, SOC, and enterprise client security reviews
- Own backup, disaster recovery, and observability for the platform
- Run the on call rotation for the platform, with the team handling initial incident response
WHO YOU ARE:
- 8+ years of experience in infrastructure, platform, DevOps, or SRE roles
- 2+ years managing engineers, or leading a team with real responsibility for people and delivery
- Deep, current, hands on experience with AWS, including multi account environments, networking, and IAM
- Strong production Kubernetes experience, ideally EKS
- Strong Terraform, including reusable modules and safe state management
- Experience building and owning CI/CD across many services
- Comfortable writing code in at least one of TypeScript, Python, or Go
- Experience in a regulated environment such as HIPAA, HITRUST, SOC 1 or SOC 2, or PCI
- Strong at running a backlog and explaining tradeoffs to stakeholders
- Clear written communicator
EXTRA CREDIT:
- Experience with Argo CD, Kafka on MSK, or Redshift and dbt infrastructure
- Cloud cost management and FinOps
- Multi region architecture on AWS
- Disaster recovery design and testing
- Familiarity with healthcare systems or handling sensitive data
- Startup or fast paced product experience
- Experience leading AI-assisted infrastructure workflows and establishing team standards around AI tooling
COMPENSATION: $160,000 - $220,000 annually, in addition to bonus and equity
Compensation offered will be determined by geographic location, experience, and qualifications.
CYBERSECURITY AWARENESS NOTICE
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.
ABOUT RIGHTWAY:
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 $300mm from investors including Khosla Ventures, Thrive Capital, Francisco Partners, and Tiger Global. We’re headquartered in New York City, with satellite offices in Denver and Dallas. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.
HOW WE LIVE OUR VALUES TO OUR TEAMMATES:
We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our core values:
1) 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.
2) 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.
3) 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.
4) 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.
5) 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 proud to be an Equal Opportunity Employer that believes in the strength of diverse thought, beliefs, backgrounds, and education. We foster an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis protected by applicable law. All employment decisions are based on merit, qualifications, need, and performance.
Skills Required
- 8+ years of experience in infrastructure, platform, DevOps, or SRE roles
- 2+ years managing engineers or leading a team with responsibility for people and delivery
- Deep, current hands-on experience with AWS, including multi-account environments, networking, and IAM
- Strong production Kubernetes experience, ideally Amazon EKS
- Strong Terraform experience, including reusable modules and safe state management
- Experience building and owning CI/CD across many services
- Ability to write code in at least one of TypeScript, Python, or Go
- Experience in a regulated environment such as HIPAA, HITRUST, SOC 1, SOC 2, or PCI
- Ability to manage a backlog and explain tradeoffs to stakeholders
- Clear written communication skills
- Experience with Argo CD, Kafka on MSK, or Redshift and dbt infrastructure
- Cloud cost management and FinOps experience
- Experience with multi-region AWS architecture
- Disaster recovery design and testing experience
- Familiarity with healthcare systems or sensitive data
- Startup or fast-paced product experience
- Experience leading AI-assisted infrastructure workflows and establishing team standards around AI tooling
Rightway Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Rightway and has not been reviewed or approved by Rightway.
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Healthcare Strength — Core coverage includes full medical, dental, and vision insurance with an HSA option, alongside additional health and wellness resources. These offerings present a comprehensive baseline of healthcare support.
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Leave & Time Off Breadth — Time off is positioned as ample, with PTO, paid sick days, holidays, and parental leave noted across employer materials. This breadth supports rest, recovery, and family needs.
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Wellbeing & Lifestyle Benefits — Perks span hybrid work, commuter benefits, in-office meals/snacks, wellness initiatives, ERGs, home-office stipends, and learning/development programs. These elements enhance everyday experience beyond core pay and insurance.
Rightway Insights
What We Do
Our care navigation and pharmacy benefits management solutions are delivered through a consumer-centric app that pairs every member with a live, clinician-led care team. By combining expert, human guidance with intuitive technology, Rightway drives members towards the best care and medication at the best price while eliminating wasteful and preventable spend.
Why Work With Us
Rightway is a company of real humans helping real humans. Join a team that's creating a better healthcare experience for all. Nothing is more important to us than the health and happiness of our members — and our employees.
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