Director, AI Strategy

Director, AI Strategy & Automation Enablement

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. We are building a portfolio of best-in-class operations supported by centralized excellence in innovation, data, and operational transformation. Our commitment to innovation and operational discipline enables our operating divisions to compete and grow in dynamic markets.

The Director, AI Strategy & Automation Enablement is a business leader responsible for defining how artificial intelligence and automation create measurable value across our underwriting, sales, operations, finance, and claims functions. This role owns the AI strategy, use-case pipeline, pilot execution, and field adoption—ensuring AI investments deliver business results and are embraced by our field teams.

Serving as the primary business owner for AI enablement, you will partner closely with Corporate IT on platforms and governance, and with Delivery teams on scaling approved initiatives. This role is intentionally positioned upstream of delivery, with authority to test, prioritize, and stop initiatives before enterprise rollout.

This is a strategy, enablement, and business decision-making role not a software engineering or IT delivery position. Success requires deep understanding of insurance operations, hands-on experience operationalizing AI tools, and the ability to translate AI capabilities into adoption-ready solutions that field teams embrace and use.

• AI Strategy & Roadmap Development
• Use-Case Management & Prioritization
• Field Partnership & Adoption Enablement
• Pilot Design, Execution & Decision Authority
• AI Evaluation Framework Ownership
• Enterprise Alignment & Governance
• Transition to Delivery

• Bachelor's degree in business, Insurance, Operations Management, or related field; MBA or advanced degree preferred.
• 10+ years of progressive experience in insurance operations, underwriting operations, or business transformation
• Demonstrated experience operationalizing AI tools (Claude, OpenAI/ChatGPT, or similar LLMs) to streamline business processes with measurable results.
• Firsthand experience implementing agentic AI, workflow automation, or document intelligence solutions in operational environments.
• Experience developing and applying AI evaluation frameworks including:
• Business case validation (ROI, capacity impact, cost-benefit analysis)
• Technical feasibility assessment (data readiness, integration complexity, accuracy thresholds)
• Adoption risk evaluation (change impact, user experience, training requirements)
• Compliance and risk assessment (regulatory implications, bias detection, audit requirements)
• Wholesale, MGA, or E&S insurance experience strongly preferred.
• Proven history leading:
• Process redesign or operational efficiency initiatives enabled by AI/automation.
• Automation, RPA, or digital enablement programs from pilot through adoption
• Cross-functional change initiatives with measurable results
• Strong facilitation, stakeholder management, and executive communication skills
• Demonstrated ability to influence senior leaders and field teams without direct authority.
• Practical, applied understanding of AI capabilities and limitations:
• LLM use cases (document summarization, data extraction, decision support)
• Agentic AI and workflow automation design
• Human-in-the-loop controls and quality assurance frameworks
• Prompt engineering and AI output validation.

• Experience building or scaling AI-powered solutions using Claude, OpenAI API, Microsoft Copilot, or similar enterprise AI platforms.
• History of moving AI from experimentation to production use with documented adoption and ROI
• Experience partnering with enterprise IT or AI teams in a business leadership capacity.
• Deep exposure to underwriting workflows, submission intake, clearance, policy servicing, or claims operations.
• Experience designing and running pilots or proofs of concept with clear scale/stop decision frameworks.
• Understanding of insurance regulatory requirements and compliance frameworks
• Familiarity with AI governance, bias detection, and responsible AI principles

Salary:

Disclosure required under applicable state or municipality regulations:
The expected salary range for this position is $140,000 to $160,000 and will be impacted by factors such as the successful candidate's skills, experience and working location, as well as the specific position's business line, scope and level. HUB International is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits, and eligible bonuses, equity and commissions for some positions.