Senior Manager, AI Solutions & Automation Delivery

Hub International Insurance • Chicago, IL

7d • Hybrid

About The Position

HUB is seeking a Senior Manager, AI Solutions & Automation Delivery, to lead end-to-end delivery of HUB's highest-impact enterprise AI Skills and Robotic Process Automation (RPA) programs. This role bridges product ownership, program management, and delivery leadership across two adjacent portfolios that have historically not had a unified delivery function. The Senior Manager works directly with COOs, the CTO, the Head of AI & Automation, and regional operations leadership to translate business priorities into shippable AI and automation outcomes, and to establish the standards, stage gates, and governance that allow these programs to scale safely. The Senior Manager partners with the Principal AI Product Owner on the AI Skills SDLC pipeline and with the Director of RPA & Automation Operations on RPA program delivery, taking ownership of cross-portfolio initiatives once they move from build into stage-gated rollout. The role is responsible for converting executive sponsorship into measurable progress across the AI and automation program portfolio.

Requirements

• Six or more years of combined experience across product management, program management, technical delivery, or solutions consulting, with at least three years in insurance, financial services, or another regulated industry.
• Demonstrated ownership of multi-stakeholder delivery programs that include both software product work and process automation work.
• Working knowledge of generative AI applications, prompt engineering concepts, and AI product validation, sufficient to drive accuracy and quality conversations with engineering and business stakeholders.
• Working knowledge of robotic process automation, including UiPath, intake processes, dispatcher and performer architectures, and production bot operations.
• Demonstrated insurance domain literacy across commercial and personal lines policy structures, claims workflows, servicing operations, and producer-facing processes.
• Track record of writing executive-grade weekly status communications, investment briefs, and decision documents for C-suite audiences.
• Demonstrated bias toward shipping, with comfort working in compressed cycles, surfacing tradeoffs, and recommending sequencing rather than waiting for direction.
• Bachelor's degree or equivalent professional experience.

Nice To Haves

• Direct experience operating inside a large-scale enterprise generative AI deployment.
• Exposure to OCR and document intelligence architectures such as Azure Document Intelligence, AWS Textract, or comparable platforms.
• Familiarity with Jira, Confluence, and SharePoint as program management substrates, including building standardized work-tracking and value-attribution patterns.
• Experience supporting cross-border or multi-region program rollouts and the operational considerations involved.
• Bilingual English and Spanish proficiency to support cross-region engagement.

Responsibilities

• Own the end-to-end delivery lifecycle for assigned enterprise AI Skills, including those selected for cross-business-unit scaling and those originating from internal innovation programs.
• Establish and maintain MVP validation criteria, stage gates, accuracy baselines, and rollout-readiness thresholds for each skill.
• Run weekly cadence reporting to executive sponsors, including operating-region COOs, Heads of Operations, the CTO, and the Head of AI & Automation, covering accuracy trends, tester expansion, account coverage, and known issues.
• Drive iteration cycles with engineering, prompt builders, and the Principal AI Product Owner to land version increments and a continuous-update cadence.
• Lead cross-functional sequencing decisions across multi-region and multi-country RPA initiatives, balancing front-end, backend, and integration work against business priorities.
• Coordinate engineering resources across vendor and HUB staff, manage capacity tradeoffs, and surface decision-ready options to business sponsors with clear effort estimates and timelines.
• Partner with the Director of RPA & Automation Operations and the RPA Manager on operational governance, including standardization of how automation work is captured, prioritized, and value-attributed across the portfolio.
• Support production bot health, exception handling, and continuous improvement across the broader automation portfolio.
• Define and document intake, stage gate, and validation methodology that applies across both AI Skills and RPA programs.
• Author executive-grade artifacts including investment briefs, scaling plans, and architecture readiness reviews.
• Maintain the working library of operating standards that the Head of AI & Automation, the Principal AI Product Owner, and the Director of RPA reference when onboarding new initiatives.
• Partner with Legal, InfoSec, Data Protection, and SDLC compliance to ensure all delivery work moves through HUB's governance framework.
• Serve as the primary delivery point of contact for executive sponsors on assigned initiatives.
• Translate technical progress and risk into business language for COOs, regional operations leaders, and the CEO when escalations or strategic milestones are warranted.
• Represent AI & Automation in operations leadership forums where assigned programs are reviewed.

Benefits

• Competitive base salary plus performance-based bonus.
• Comprehensive medical, dental, and vision coverage.
• 401(k) with company match.
• Paid time off and company holidays.
• Flexible work arrangements including remote and hybrid options.
• Professional development and certification reimbursement.
• Access to cutting-edge AI tools and technologies.
• Opportunity to shape the AI and automation strategy of a leading global insurance brokerage.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior