Head of Annotation Operations

Head Of Annotation Operations

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.

Why Obvio

• Your work will help save lives and improve road safety
• Series A of $22M led by Bain Capital
• Fast-moving startup environment with meaningful ownership
• Competitive compensation and early-stage equity

Obvio is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Obvio considers qualified applicants with criminal histories, consistent with applicable federal, state, and local law. Obvio is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please let your recruiter know.