Apprentice International Program Manager Jobs in Chicago, IL

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

• Partner with product owners to intake initiative roadmaps and translate them into actionable program plans with clear milestones, dependencies, and resource needs
• Drive day-to-day execution across active programs, proactively identifying and removing blockers, managing interdependencies, and keeping delivery on track
• Coordinate across technology teams, vendors, and stakeholders to align on sequencing, capacity, and delivery commitments
• Maintain program-level visibility through consistent status reporting, risk tracking, and issue escalation, so leadership has an accurate, timely picture of progress
• Support pilot and rollout activities by coordinating readiness across technology, change management, and operations teams

• 5+ years of program management experience, with a strong track record of driving delivery in complex, matrixed technology organizations
• Demonstrated ability to manage across program types and technology domains, and to pick up new program areas quickly
• Background supporting organizational launches or capability stand-ups, managing the execution side of structural transitions
• Exposure to enterprise technology environments, such as infrastructure, enterprise applications, security, or similar

• Exceptional execution discipline. You follow through, close loops, and don't let things fall through the cracks
• Strong ability to translate strategic direction into structured plans, timelines, and delivery cadences
• Skilled at navigating ambiguity and managing competing priorities without losing momentum
• Clear, confident communicator who can adapt messaging for technical teams, change leads, and executive stakeholders

• PMP, PgMP, or equivalent program management certification
• Exposure to change management methodologies (Prosci, ADKAR)
• Experience in insurance, financial services, or other regulated industries
• Familiarity with AI governance principles, responsible AI frameworks, or other emerging technology governance practices

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 joinHUB International, you will be part of a community of learners and doers focused on our Core Values: entrepreneurship, teamwork, integrity, accountability, and service.

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, HAS and 401(k) accounts, paid-time-off benefits such as vacation, sick, personal, floating holidays and company holidays. In addition, eligible annual bonuses, equity and commissions may be available for some positions.

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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