Senior Director of Site Reliability and Software Engineering, Jellyvision

• You’re a strategic yet hands on leader, with deep technical expertise and a track record of running mission critical HR and Benefits technology platforms
• You understand how to scale an SRE organization to be obsessively focused on customer reliability and experience
• You have a proven track record of taking good engineering teams and making them great, while balancing the competing demands of feature delivery, system reliability, and cost optimization
• You thrive in complex, regulated environments where uptime isn't just a metric—it's essential to helping people access their healthcare and benefits when they need them most
• Strategic and hands-on. You move seamlessly between big-picture thinking and in-the-weeds execution. You’re comfortable getting into the details to drive decisions and improvement
• A strong people leader. You build high-performing, motivated teams. You coach, develop, and inspire others to do their best work and grow with the company
• Executive savvy, team-first. You can influence at the highest levels while staying grounded in the needs of your team. You advocate for your people and keep alignment clear across all layers of the org
• Comfortable with ambiguity. You thrive in fast-moving environments with legacy complexity and new greenfield opportunities. You know how to push forward even when the data’s incomplete
• Curious and driven. You’re energized by learning, solving real problems, and making things better—for users, customers, and the business. You bring grit, heart, and momentum to everything you lead
• 12+ years of software engineering experience with 6+ years in SRE, DevOps, or infrastructure leadership roles
• Bachelor's degree in Computer Science, Engineering, or related field (Master's preferred)
• 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 ability to make data-driven decisions on technology investments
• Excellent written and verbal communication skills with 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

Desirable

• We’re on a mission to simplify benefits and empower employers, brokers, and employees with smarter, more human technology
• We are seeking an exceptional Senior Director of Site Reliability Engineering & Software Engineering to lead our mission-critical infrastructure and engineering excellence initiatives
• This strategic leadership role combines hands-on technical expertise with executive-level decision making to build world-class SRE capabilities while driving core product delivery and technology optimization
• As a key member of our engineering leadership team, you'll be responsible for elevating our SRE organization, establishing industry-leading practices, and driving strategic technology decisions that simplify our platforms and improve performance
• 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
• Own and execute 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
• Partner with Product and Engineering leadership to ensure reliable, scalable delivery of customer-facing features
• 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
• 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
• We are growing and scaling at a fast pace and this role is critical to client satisfaction and business growth. As a key member of the technology leadership team you have the opportunity to drive the future direction of our platforms