Vice President of AI and Automation (Chicago)

ABOUT US

At HUB International , we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence.

HUB is the 5th largest global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions.

Position Overview:

HUB International is seeking a strategic and execution-focused Vice President of AI & Automation to lead the enterprise-wide adoption, development, and governance of AI and automation initiatives. This strategic role will shape and deliver transformative capabilities that enhance operational efficiency, employee productivity, customer engagement, and competitive advantage across HUB’s expansive brokerage network.

Summary:

As the VP of AI & Automation , you will play a pivotal leadership role in shaping HUB’s future through transformative AI and automation technologies. This role is central to the transition of HUB from the 'exploration' phase to enterprise-wide AI enablement, where innovation meets rigorous governance.

You will drive HUB’s five AI strategic pillars—from Foundational, Vendor, Digital, Custom, and RPA. You will oversee the full AI delivery lifecycle, from proof-of-concept to governed deployment, ensuring each solution drives measurable business value, aligns with compliance and risk protocols, and empowers employees and clients alike.

The ideal candidate blends enterprise AI knowledge with a track record of large-scale digital transformation. You’ll bring an ability to orchestrate product and technical squads, business sponsors, and governance leaders toward common outcomes. You’ll champion responsible innovation—embedding AI into key areas of our business processes like sales enablement, servicing, onboarding, policy servicing, and customer engagement workflows through automation, intelligent orchestration, and human-in-the-loop experiences.

This role requires close alignment and collaboration with HUB’s core business lines and leaders, legal, security and compliance teams and the broader IT organization to ensure consistent, value added and secure solutions. By working across these groups, you’ll ensure that AI efforts are integrated, compliant, strategically grounded, and successfully adopted across the enterprise.

You’ll also serve as HUB’s executive ambassador for AI strategy, translating complex AI opportunities into impactful, user-friendly experiences, while managing vendor partnerships, product delivery, and change adoption across the enterprise.

Key Responsibilities: Strategy & Vision

• Define and champion HUB’s enterprise AI & automation roadmap in alignment with business strategy.
• Build a forward-looking portfolio focused on five strategic pillars:
• Baseline GenAI, ML and AI capability
• Onboarding Enablement
• Sales & Servicing capabilities and vendor capability
• AI-Powered RPA and Document Ingestion
• Digital D2C AI Capabilities

Execution Leadership

• Ability to translate strategic business process into value added strategic AI delivery capability
• Oversee the delivery of key MVPs and scale across business lines.
• Partner with product, engineering, application, technology, data and business leaders to build and deploy intelligent automation across identified HUB business areas
• Establish a Center of Excellence and agile squads to develop, test, and scale AI products.
• Strong customer service and servant leadership across a dynamic and decentralized business ecosystem

Governance & Risk

• Serve as executive sponsor of the AI Governance Board, ensuring all AI use cases comply with security, privacy, legal, and ethical standards.
• Establish “human-in-the-loop” safeguards, change management, and knowledge scoping across solutions.
• Lead the third-party AI vendor assessment process, selecting and overseeing partnerships with identified AI vendors.

Change Management & Enablement

• Drive user adoption by collaborating with HR, Comms, and L&D to deploy role-specific training and AI playbooks.
• Create enterprise-wide success metrics and feedback loops to monitor performance and value realization.
• Empower HUB’s workforce through productivity-enhancing AI embedded in daily tools like M365, Teams, and CRM systems.

Qualifications:

• 10+ years of leadership experience in AI, digital transformation, or enterprise technology strategy.
• Proven track record of deploying AI or intelligent automation initiatives in complex, regulated industries (insurance/financial services preferred).
• Background in AI product management, enterprise change leadership, or managing technical squads in Agile/Scrum environments.
• Deep familiarity with AI governance frameworks, model risk management, and compliance in enterprise environments such as NIST, AI RMF, OECD or ISO/EIC 42001
• Strong expertise in Microsoft 365 ecosystem, OpenAI/LLM technologies, RPA platforms (e.g., UiPath), and cloud (Azure, AWS, or GCP).
• Demonstrated ability to lead cross-functional teams, scale POCs to enterprise products, and communicate complex strategies to executive stakeholders.
• Background in AI product management, enterprise change leadership, or managing technical squads in Agile/Scrum environments.

Preferred Experience:

• Knowledge of the insurance industry and insurance brokerage
• Familiarity with agentic automation and AI orchestration concepts.
• Knowledge of digital direct to consumer platforms and the application of AI to those sales and servicing workflows

JOIN OUR TEAM

Do you believe in the power of innovation, collaboration, and transformation? Do you thrive in a supportive and client focused work environment? Are you looking for an opportunity to help build and drive change in a rapidly growing and evolving organization? When you join HUB International , you will be part of a community of learners and doers focused on our Core Values: entrepreneurship, teamwork, integrity, accountability, and service.

Disclosure required under applicable law in California, Colorado, Illinois, Maryland, Minnesota, New York, New Jersey, and Washington states: The expected salary range for this position is $250,000 o $300,000 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. If you believe that your qualifications and experience surpass the minimum requirements for this role, we encourage you to submit your application. By doing so, we will be able to keep your application on file for consideration for potential future positions within our organization. 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 such as vacation, sick, and personal days, and eligible bonuses, equity and commissions for some positions.

Department Information Technology Required Experience: 10-15 years of relevant experience Required Travel: Negligible Required Education: Bachelor's degree (4-year degree)

HUB International Limited is an equal opportunity employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations.

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