Director, AI Strategy

About SPG

SPG is a specialty insurance holding company focused on acquiring and scaling Managing General Agents (MGAs) and Wholesalers in the E&S and specialty insurance markets. It builds a portfolio of best‑in‑class operations supported by centralized excellence in innovation, data, and operational transformation.

The Director, AI Strategy & Automation Enablement is a business leader responsible for defining how artificial intelligence and automation create measurable value across underwriting, sales, operations, finance, and claims. The role owns the AI strategy, use‑case pipeline, pilot execution, and field adoption, ensuring AI investments deliver business results and are embraced by field teams. It partners closely with Corporate IT on platforms and governance and with Delivery teams on scaling approved initiatives.

This is a strategy, enablement, and business decision‑making role—not a software engineering or IT delivery position.

Define and maintain a 12–24‑month AI and automation roadmap aligned to enterprise priorities. Establish a strategic point of view on how AI supports underwriting leverage, operational efficiency, and scalability across portfolio companies. Translate emerging AI capabilities into practical, business‑ready opportunities. Provide executive leadership with regular updates on priorities, progress, outcomes, and ROI.

Lead a structured intake process for AI and automation opportunities from underwriting, sales, operations, finance, and claims. Define and apply qualification criteria for AI‑ready use cases—business value, technical feasibility, adoption readiness, risk profile—and quantify expected benefits. Own and manage the enterprise AI use‑case backlog and prioritization framework.

Design and facilitate structured focus groups with field underwriting and operations teams. Partner with business leaders to validate problem statements, pressure‑test workflows, and identify adoption barriers early. Build and maintain an AI Champion Network to drive engagement and change readiness. Ensure field feedback directly informs pilot design, iteration, and scale decisions.

Design, execute, and evaluate time‑boxed AI pilots (typically 30–90 days). Define pilot success metrics, adoption thresholds, and clear exit criteria. Evaluate pilot results using a standardized framework and make formal recommendations to scale, iterate, defer, or stop initiatives. Serve as the decision gate between experimentation and enterprise implementation.

Develop and maintain a comprehensive evaluation framework for assessing AI opportunities from intake through scale decision. Establish qualification scorecards, pilot design standards, success criteria, and scale/stop decision thresholds. Create repeatable methodology for measuring accuracy, business impact, adoption signals, and ROI. Define production monitoring standards—including accuracy drift detection, adoption tracking, and value realization measurement.

Partner with Corporate IT to align pilots with enterprise strategy, approved platforms, security standards, and governance requirements. Collaborate with Digital Strategy to ensure alignment with enterprise architecture and data strategy. Coordinate with Compliance, Legal, Risk, and IT Security on responsible AI practices. Support development of AI usage standards, guardrails, and human‑in‑the‑loop controls. Maintain documentation for audit and regulatory readiness.

Partner with Delivery & Implementations to transition approved initiatives into operational execution. Provide clear business requirements, target workflows, adoption plans, and success metrics to scale implementations. Maintain separation between pilot ownership and large‑scale delivery execution.

Bachelor’s degree in business, insurance, operations management or related field; MBA or advanced degree preferred. Over 10 years of…