Head of Technical Operations – Advocate

About Advocate

Advocate is redefining how people access and manage benefits. We combine compassionate claimant representation with advanced technology to simplify and accelerate the SSDI and SSI process — and our long-term vision is to build the benefits infrastructure that supports individuals across multiple federal and state programs.

The Role

We’re seeking a Head of Technical Operations to serve as the connective tissue between our technology platform and our operations teams. You’ll ensure that our systems, automations, and data infrastructure power a seamless user experience — for both claimants and our internal teams. You’ll partner closely with the Head of Operations, aligning technology with business strategy, ensuring systems scale efficiently, and supporting operational success through smart, reliable, and automated processes. You’ll also work directly with the CTO to define and execute the roadmap that connects our product and service layers. This role blends strategic thinking with hands-on execution. You should enjoy diving into details, troubleshooting issues, and building systematic, scalable solutions that reduce complexity and make every part of our operations smoother.

• Bridge Technology and Operations
• Serve as the technical counterpart to the Head of Operations, translating operational goals into technical systems and data workflows.
• Collaborate across teams to ensure Salesforce, our internal platform, and other tools operate cohesively and transparently.
• Develop business rules and process logic that create clean, traceable workflows between humans and AI systems.

• Drive Automation and User Experience
• Oversee the technical aspect of communications platforms and automations that ensure every claimant interaction feels seamless, timely, and human.
• Partner with Operations to map and automate core workflows, improving speed, accuracy, and user satisfaction.
• Help build systems that enable proactive communication, follow-up, and escalation handling across channels (email, text, chat).

• Ensure Data Integrity and Insight
• Maintain a disciplined data model and ensure all data flows through well-defined, auditable interfaces.
• Implement dashboards and monitoring tools to track performance, identify bottlenecks, and support decision-making.
• Enable data-driven insights for the operations team through clear metrics, alerts, and reporting infrastructure.

• Troubleshoot and Systematize
• Roll up your sleeves to diagnose and resolve technical and operational issues as they arise.
• Develop systematic fixes and document playbooks to prevent recurrence and promote consistent execution.
• Partner with engineering to prioritize and deliver sustainable, elegant solutions rather than one-off patches.

• Design for the Future
• Collaborate with leadership to envision and implement an end-to-end automated operations system that’s robust, simple, and scalable.
• Continuously look for ways to improve efficiency and reduce manual work through thoughtful design and automation.
• Ensure all systems reflect a deep understanding of Advocate’s operational model, data dependencies, and user journey.

• You have a strong background in engineering, technical program management, and operations systems design.
• You understand how to make technology serve the business, not the other way around.
• You’re comfortable integrating systems like Salesforce, AI-driven tools, and workflow automation platforms.
• You’re equally happy writing specs, mapping data flows, or jumping in to troubleshoot an issue in real time.
• You take a long-term view — aiming for elegant, maintainable systems that scale with growth.
• You’re collaborative, curious, and committed to improving how people access the benefits they deserve.

• Event-driven architectures (Kafka/Kinesis/EventBridge)
• Multi-tier data platforms (Aurora, DynamoDB, OpenSearch, S3)
• Orchestration (Temporal, Step Functions, custom engines)
• Real-time processing (Flink/Kinesis Analytics)
• Container orchestration (ECS/EKS)
• Infrastructure as Code (CDK/Terraform)
• AI/ML pipelines throughout
• Salesforce configuration and development, Salesforce Apex Programming
• Vendor technology setup, operations / configuration: ZenDesk, Ring Central, Customer IO

This is a hybrid role requiring travel about six times a year for in-person working sessions, primarily on the West Coast (with flexibility as needed).