Manager, Site Reliability Engineering

Jellyvision•Chicago, IL

1d•$160,000 - $170,000•Remote

About The Position

Jellyvision ALEX® , is on a mission to improve lives by helping people choose and use their benefits. We are raising the bar—for benefits and the employee experience (for our employees and those of the customers we serve) – by scaling personalization, compassion and an earnest intent to be helpful in all that we do. Jellyvision people are a group of creative problem solvers who use good judgment, give each other honest feedback, engage in real debate, and snack frequently. We are curious, hungry, and humble—because we know this is how we’ll continue to make an impact. We’re kind, biased towards action, and sweat the details to create great experiences for those we serve. We are an inclusive, human-first workplace. Respect and trust for each other are foundational, and our equitable total rewards offerings support the lives and holistic well-being of our unique people. At Jellyvision, expect career experiences that challenge you, empower you to have a direct impact on our mission, and enable you to learn, try, and do while having fun along the way. We’re on a mission to simplify benefits and empower employers, brokers, and employees with smarter, more human technology. We are seeking an exceptional Manager of Site Reliability Engineering to lead our mission-critical infrastructure and engineering excellence initiatives. This strategic leadership role combines hands-on technical expertise with manager-level decision-making to build world-class SRE capabilities while driving core product delivery and technology optimization. Reporting to the VP of Information and Security, you will be a key member of our engineering team, responsible for elevating our SRE organization, establishing industry-leading practices, and driving strategic technology decisions that simplify our platforms and improve performance.

Requirements

6+ years of software engineering experience with 2+ years in SRE, DevOps, or infrastructure leadership roles
Proven experience building and scaling SRE teams at high-growth technology companies
Deep expertise in cloud platforms (AWS, GCP, Azure), containerization (Kubernetes, Docker), and Infrastructure as Code
Strong background in distributed systems, microservices architecture, and database technologies
Experience with monitoring and observability tools (Dynatrace, DataDog, New Relic, etc.)
Experience with AI automation and Workflow optimization tools
Demonstrated success leading engineering teams composed of FTEs and offshore contractors
Track record of driving significant cost reductions through technology optimization and consolidation
Experience managing complex technical roadmaps with competing priorities and resource constraints
Strong analytical skills with the ability to make data-driven decisions on technology investments
Excellent written and verbal communication skills with the ability to present to executive audiences
Experience translating technical concepts into business impact and ROI metrics
Proven ability to influence cross-functional teams and drive consensus on technical decisions

Nice To Haves

Experience in benefits administration, healthcare technology, or highly regulated industries
Bachelor's degree in Computer Science, Engineering, or related field (Master's preferred)
Background with HRIS integrations, API management, and enterprise software platforms
Knowledge of compliance frameworks and security best practices in cloud environments
Previous experience with technology cost optimization initiatives with tangible savings

Responsibilities

SRE Leadership and Team Development
Directly manage a team of onshore and offshore software engineers
Lead and elevate our existing SRE team to world-class performance standards, advancing career development and technical excellence
Optimize and mature our established SRE practices, enhancing SLO/SLI frameworks, error budget management, and incident response effectiveness
Strengthen our culture of reliability and observability, driving higher standards for continuous improvement across all engineering teams
Refine existing on-call processes, escalation procedures, and post-incident reviews to accelerate learning and prevent recurring issues
Drive an AI-first agenda, leveraging AI tooling to address key pain points and improve speed to market
Strategic Technology Leadership
Partner with Product and Engineering leadership to help deliver the core product technology roadmap, balancing feature delivery with reliability and scalability requirements
Drive strategic decisions on technology consolidation and simplification to reduce operational overhead and costs
Lead technology platform evaluations and migrations that align with business objectives and cost optimization goals
Operational Excellence
Implement comprehensive monitoring, alerting, and observability solutions across all systems
Establish reliability engineering practices, load testing, and capacity planning
Drive automation initiatives that reduce manual toil and improve system reliability
Create and maintain disaster recovery and business continuity plans
Cross-functional Collaboration
Work closely with Platform & Infrastructure, Product Development, and Security teams to ensure aligned priorities
Collaborate with Finance and Operations teams on cost optimization and resource planning initiatives
Present technical strategies and progress to executive leadership