Head of Annotation Operations

About the Role

Obvio’s enforcement system depends on accurate, consistent, and auditable human review. We are hiring a Head of Annotation Operations to own our annotation and review function end-to-end as we scale.

This role will lead a team that will substantially grow over the next year. You will design and operate the workflows, quality systems, training programs, and performance management needed to run a high‑throughput, safety‑ and compliance‑critical operation.

What You’ll Do

Annotation Operations & Workflow Ownership

• Own execution and continuous improvement of Obvio’s annotation and review workflows for automated traffic enforcement.
• Translate enforcement requirements and edge cases into clear reviewer guidelines, task specs, and escalation paths.
• Balance throughput, accuracy, and consistency in a high-stakes operational environment.

Scaling the Organization

• Design the operating model for a rapidly scaling review organization, including team structure, lead roles, and QA functions.
• Lead hiring, onboarding, and ramp programs to ensure reviewers reach proficiency quickly.
• Build and run performance management systems including coaching, feedback, and accountability.

Quality, Auditability & Risk Management

• Define and maintain rubrics, golden datasets, calibration packs, and edge‑case decision trees.
• Implement QA systems such as sampling, double review, adjudication, and calibration sessions.
• Reduce quality escapes and build preventative controls for high-risk review categories.
• Ensure documentation, version control, and audit readiness across all annotation workflows.

Metrics, Capacity & SLAs

• Own forecasting, staffing models, and capacity planning tied to volume growth and city deployments.
• Build dashboards and operating reviews covering accuracy, agreement, throughput, backlog, rework, cost, and SLA adherence.
• Identify bottlenecks and execute improvements across people, process, and tooling.

Tooling & Cross‑Functional Partnership

• Partner closely with Product, Engineering, and ML to improve reviewer tooling, automation, and queueing logic.
• Establish human‑in‑the‑loop feedback loops that improve model performance and reduce reviewer burden over time.
• Ensure secure and auditable operational workflows.

Stakeholder Communication

• Serve as the primary owner for annotation operations with leadership and cross‑functional partners.
• Provide clear, regular updates on status, quality trends, risks, and mitigation plans.
• Build scalable playbooks and documentation as the organization grows.

Who You Are

Required Experience

• 7+ years in operations leadership, program management, or process‑heavy environments (e.g., trust & safety, compliance ops, fraud, payments, BPO, customer support ops, or data labeling).
• 3+ years managing people, including building lead or manager layers.
• Proven experience scaling teams and workflows while improving quality and reliability.
• Strong process design skills with the ability to turn ambiguity into clear SOPs and measurable outcomes.
• Excellent written communication skills, especially for guidelines and edge‑case documentation.
• Data‑driven operator comfortable using metrics and dashboards to run the business.

Operating Mindset

• High ownership mentality with accountability for outcomes.
• Calm and structured in high‑stakes, fast‑moving environments.
• Collaborative and effective across operations, engineering, and leadership.
• Bias toward action and continuous improvement.

Nice to Have

• Experience in regulated or compliance‑sensitive review workflows requiring auditability.
• Familiarity with inter‑annotator agreement, calibration design, and statistical QA methods.
• Experience with annotation or review tooling (commercial or custom).
• Background in enforcement‑adjacent, public sector, or safety‑critical operations.
• Startup experience building systems from first principles.