Vice President of AI and Automation (Chicago) Job at Lensa, Chicago, IL

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  • Lensa
  • Chicago, IL

Job Description

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Lensa is a career site that helps job seekers find great jobs in the US. We are not a staffing firm or agency. Lensa does not hire directly for these jobs, but promotes jobs on LinkedIn on behalf of its direct clients, recruitment ad agencies, and marketing partners. Lensa partners with DirectEmployers to promote this job for HUB International. Clicking Apply Now or Read more on Lensa redirects you to the job board/employer site. Any information collected there is subject to their terms and privacy notice.

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 a 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 HUBs expansive brokerage network.

Summary

As the VP of AI & Automation , you will play a pivotal leadership role in shaping HUBs 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 HUBs five AI strategic pillarsfrom 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. Youll bring an ability to orchestrate product and technical squads, business sponsors, and governance leaders toward common outcomes. Youll champion responsible innovationembedding 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 HUBs 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, youll ensure that AI efforts are integrated, compliant, strategically grounded, and successfully adopted across the enterprise.

Youll also serve as HUBs 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 HUBs 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 HUBs 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 candidates skills, experience and working location, as well as the specific positions 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.

E-Verify Program (

We endeavor to make this website accessible to any and all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please contact the recruiting team HUBRecruiting@hubinternational.com . This contact information is for accommodation requests only; do not use this contact information to inquire about the status of applications.

If you have questions about this posting, please contact support@lensa.com

Seniority level

  • Seniority level

    Executive
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Job Tags

Full time, Local area,

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