Online Team Leader

About Chubb

Chubb is the world's largest publicly traded property and casualty insurance company. With operations in 54 countries and territories, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance and life insurance to a diverse group of clients. As an underwriting company, we assess, assume and manage risk with insight and discipline. We service and pay our claims fairly and promptly. The company is also defined by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength and local operations globally. Parent company Chubb Limited is listed on the New York Stock Exchange (NYSE: CB) and is a component of the S&P 500 index. Chubb maintains executive offices in Zurich, New York, London, Paris and other locations, and employs approximately 33,000 people worldwide. Additional information can be found at:

Interested applicants need to submit both a CV and a cover letter for this role.

About the Role

The way insurance operations are led is changing — and this role puts you at the frontier of that transformation.

As Digital Team Leader within Chubb’s Operations Hub for Continental Europe, based in Madrid, you will lead a team of Underwriting Operations Technicians across our Online and Submissions functions — professionals who work every day at the intersection of AI automation and expert human judgment. Your team does not simply process transactions; they govern the AI‑assisted workflows that handle Chubb’s European portfolio, stepping in with expertise where automation reaches its limits.

This role demands more than traditional people management. You will oversee autonomous decision‑making, monitor agent performance, and ensure that the combined output of human and machine meets the highest standards of quality, compliance, and client service. You will be a multiplier: developing your team’s ability to exercise sound judgment precisely because routine work is handled by automation.

Key Responsibilities

Team Leadership & AI-Augmented Workforce Development

• Lead, coach, and develop a team of Underwriting Operations Technicians (Online and Submissions), fostering a culture where human expertise and AI capability reinforce each other.
• Manage work allocation across automated and human‑handled queues, ensuring the right balance between straight‑through processing (STP) throughput and human exception quality.
• Conduct regular performance reviews and one‑to‑ones with a focus on developing human‑in‑the‑loop (HITL) judgment — the ability to make sound, auditable decisions on cases that AI cannot resolve.
• Actively preserve institutional knowledge: as routine work shifts to automation, ensure your team deepens rather than loses the expertise that makes their exception decisions trustworthy.
• Support team members in building AI literacy — not as technologists, but as confident, critical users who understand what the system can and cannot do.
• Manage escalation paths, ensuring complex cases reach the right people — underwriters, specialist teams, or the Operations Manager — with full context captured.
• Perform additional duties as assigned by the Head of Digital Operations, including cross‑functional project support.
• Monitor AI decision patterns across submission scoring, exception routing, and STP processing — identifying signals of model drift, rules‑engine gaps, or systematic errors before they affect portfolio quality.
• Set, review, and adjust STP confidence thresholds and variance limits in collaboration with operations and technology stakeholders, balancing automation throughput against the risk of error.
• Review and sign off on daily SOX and AI governance reports, maintaining the audit trail that regulators and internal controls require.
• Collect structured operational feedback from your team and channel it into model improvement cycles — frontline experience is the most valuable input to continuous AI learning.
• Participate in testing and validating AI workflow changes before production deployment, acting as the operational voice that bridges technical design and day‑to‑day operational reality.
• Ensure control processes are executed and reported accurately, including premium reconciliation, peer review auditing, and Contract Certainty obligations.
• Monitor SLA performance across all work streams — automated, retained, and outsourced — and take corrective action when delivery standards are at risk.
• Conduct audits and quality control checks on AI‑assisted and manually processed work, ensuring outputs meet Chubb’s standards of accuracy and compliance regardless of how they were produced.
• Support user acceptance testing (UAT) of system and AI workflow changes, representing operational requirements in the testing process.
• Regularly review team processes for efficiency, identifying non‑value steps and opportunities to extend automation safely.

Operational Excellence & Service Delivery

• Collaborate with the Head of Digital Operations to align team goals with broader digital transformation objectives, and support the implementation of strategic automation initiatives.
• Produce and present management information on team performance, automation performance, and exception trends — providing the insight leadership needs to make informed decisions.
• Build and maintain strong relationships with underwriters, brokers, internal customers, and third‑party service providers, representing operational capabilities and constraints clearly.
• Act as a change champion: translate evolving automation capabilities into clear team practices, and help colleagues see change as opportunity rather than disruption.