Remote Observability Jobs in Boca Raton, FL (NOW HIRING)

NationsBenefits is recognized as one of the fastest-growing companies in America and a Healthcare Fintech provider of supplemental benefits, flex cards, and member engagement solutions. We partner with managed care organizations to provide innovative healthcare solutions that drive growth, improve outcomes, reduce costs, and bring value to their members.Through our comprehensive suite of innovative supplemental benefits, fintech payment platforms, and member engagement solutions, we help health plans deliver high-quality benefits to their members that address the social determinants of health and improve member health outcomes and satisfaction.Our compliance-focused infrastructure, proprietary technology systems, and premier service delivery model allow our health plan partners to deliver high-quality, value-based care to millions of members.We offer a fulfilling work environment that attracts top talent and encourages all associates to contribute to delivering premier service to internal and external customers alike. Our goal is to transform the healthcare industry for the better! We provide career advancement opportunities from within the organization across multiple locations in the US, South America, and India.
Location: Remote (US-based candidates only)
Manager, Site Reliability Engineering (SRE)Position Overview

We are seeking a Manager, Site Reliability Engineering (SRE) to lead our US-based SRE team and drive operational excellence across our production platforms.

This is a player-coach leadership role that combines people management with hands-on technical leadership. You will mentor and grow a team of Site Reliability Engineers while actively participating in major incident response, reliability initiatives, and operational reviews. The role is a key part of our global follow-the-sun support model and requires close collaboration with SRE leadership in India.

Key ResponsibilitiesTeam Leadership & Development

• Lead, mentor, and develop a US-based team of Site Reliability Engineers.
• Conduct regular 1:1s, performance reviews, and career development discussions.
• Own hiring, onboarding, and retention efforts as the team scales.
• Foster a culture of ownership, blameless postmortems, and continuous improvement.

Operational Excellence & Incident Management

• Lead day-to-day production operations and ensure timely incident triage, resolution, and escalation.
• Serve as an escalation point and incident commander for major production incidents.
• Drive problem management and root cause analysis processes.
• Carry PagerDuty on-call escalation responsibilities for critical issues.
• Track and report operational KPIs, SLAs, and SLOs, including availability, MTTR, and incident trends.

Reliability & Automation

• Improve system reliability, observability, and resilience using Datadog and related tooling.
• Drive automation, self-healing capabilities, and runbook maturity.
• Partner with Development, DevOps, DevSecOps, and Engineering teams to embed reliability into the SDLC.
• Contribute hands-on to tooling, automation, and technical reviews as needed.

Collaboration & Global Alignment

• Coordinate closely with SRE leadership in India to ensure seamless follow-the-sun coverage.
• Represent the US SRE organization in cross-functional planning and operational reviews.
• Communicate effectively with both technical and non-technical stakeholders.

Documentation & Compliance

• Maintain high-quality documentation for incidents, postmortems, runbooks, and operational procedures.
• Ensure adherence to healthcare and fintech compliance standards, including HIPAA, PCI DSS, SOC 2, ISO 27001, and HITRUST.

Required Qualifications

• 58 years of experience in Site Reliability Engineering, DevOps, Production Support, or Platform Engineering.
• 12+ years of experience leading, mentoring, or managing engineers.
• Demonstrated success operating in a player-coach leadership model.
• Strong hands-on experience with production incident management and escalation processes.
• Proficiency with Datadog or similar observability platforms.
• Hands-on experience with Kubernetes and Docker in production environments.
• Strong scripting or programming skills in PowerShell, Bash, Python, Java, or C#.
• Experience with Helm, CI/CD pipelines, and deployment automation.
• Working knowledge of ITIL processes and Agile methodologies.
• Experience working with SQL, MySQL, or NoSQL databases.
• Excellent communication and stakeholder management skills.
• Willingness to participate in PagerDuty on-call escalation and work within a global follow-the-sun operating model.

Preferred Qualifications

• Experience with cloud platforms such as AWS, Azure, or GCP.
• Experience building or scaling SRE teams and on-call programs.
• Experience defining and managing SLOs, SLIs, and error budgets.
• Prior experience in the healthcare or fintech industry.
• Knowledge of security and compliance frameworks relevant to regulated environments.

Why Join NationsBenefits?

• Competitive compensation and comprehensive benefits.
• Unlimited PTO.
• Fully remote work environment (US-based).
• Opportunity to lead and grow a high-impact SRE organization.
• Exposure to modern cloud-native technologies and large-scale reliability challenges.
• Collaborative culture focused on innovation, learning, and continuous improvement.
• Meaningful work that directly impacts healthcare technology and millions of members.

Ideal Candidate

We are looking for a technically strong SRE leader who enjoys building teams, improving operational maturity, and remaining hands-on during critical production events. The ideal candidate combines leadership, systems thinking, and automation expertise to help scale reliability practices across a fast-growing Healthcare FinTech organization.
NationsBenefits is an Equal Opportunity Employer.