Technology and Operations Delivery PMO DirectorChicago, IL

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 more than 17,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions.


At HUB International the Technology and Operations Delivery PMO Director holds both the leadership and management roles of a program management office whose focus is to support enterprise-affecting programs and projects. The Delivery PMO Director oversees the delivery of complex technology projects across the organization and ensures that the PMO adds value, is relevant to the strategy of the organization, and serves, supports and enables the organization’s projects, programs and structured [or unstructured] work efforts. The Director will embody and lead a culture of service, quality, risk management, and enabling governance that is focused on results. Working closely with technical subject matter experts, department leaders, product managers, engineers, application owners, business partners, and cross-functional stakeholders, the PMO Director co-owns the development of integrated plans to buildout a transparent, realistic, and actionable roadmap of initiatives that support strategic goals. The Director will own the tool set/s and communication channels that support the work of the PMO, championing features and managing inputs and outputs for the benefit of all stakeholders. The Director also provides strategic guidance, coaching, and mentoring to the PMO staff and project teams.

Primary Responsibilities and Activities

  • Defines, manages and directs the needed end-to-end PMO work effort, which includes leveraging best practices and techniques in identifying, quantifying and tracking the realization of expected benefits defined in business cases in partnership with a myriad of project stakeholders.

  • Provides technical insight and context to PMO staff to bolster technology context, facilitate project engagement, and optimize project approach

  • Ensures alignment of project portfolio with organizational strategy, vision, and goals

  • Monitors and reports on project performance, status, risks, issues, and benefits realization

  • Facilitates among the PMO stakeholders and organizational leadership a consensus around the mission and vision of the PMO organization to foster a project-management-oriented culture and mindset

  • Leads the identification and development of PMO roles, team configuration and recruitment appropriate to deliver the agreed-upon PMO goals and objectives across management methodologies

  • Establishes a stable framework that supports all project teams and stakeholders to improve the probability of successful project delivery

  • Provides ongoing coaching and mentoring to PMO staff and project managers, identifying training needs and building a corresponding training plan. Identifies areas for organizational agility as the company adopts best-practice development methodologies where appropriate.

  • Builds and maintains relationships with senior leadership and key PMO stakeholders, and acts as a trusted advisor. Builds strong communication and change networks to create a strong customer orientation across the PMO.

  • Regularly reviews and evaluates opportunities to improve the project management practices in order to achieve higher maturity in PPM

  • Leads the establishment of a project management community of practice to facilitate collaboration and best-practice sharing among project managers and key PMO stakeholders

Primary Contacts

  • Cross-functional TechOps Leaders and Team Members

  • Project, program and portfolio managers

  • Corporate and Field leadership

Job Requirements

Education: Bachelor’s or master’s degree in computer science, information systems, business administration or related field, or equivalent work experience


  • Fifteen or more years of experience in IT and business/industry

  • Ten or more years of leadership responsibilities

  • Ten or more years of program and project management responsibilities

  • Demonstrated experience in leading diverse project teams

  • Proven track record of leading and delivering complex, cross-functional, and strategic projects.

Knowledge and Skills

  • Excellent, clear, direct, compelling verbal and written communication and presentation skills, including the ability to explain IT concepts and technologies to business leaders and business concepts to the PMO staff.

  • Direct experience with a variety of project management methodologies

  • Program management skills and experience

  • Significant knowledge of project planning tools with evidence of practical application

  • Exceptional leadership skills with the ability to develop and communicate the PMO vision and inspire and motivate PMO staff.

  • A distinctive blend of people, business, IT, financial and communication skills.

  • Effective influencing and negotiation skills in an environment where resources may not be in direct control of this role.

  • Excellent analytical, strategic conceptual thinking, strategic planning and execution skills.

  • Strong business acumen.

  • Deep understanding of current and emerging technologies.

  • Demonstrated ability to develop and execute a strategic resource plan.


  • Demonstrates strong emotional intelligence and respect for others

  • Works daily with a planful, motivational, service-minded and goal-oriented attitude

  • Encourages and facilitates cooperation and results

  • Fosters an environment of collaboration and transparency

  • Inspires, motivates and guides team members

  • Fosters commitment, team spirit, pride and trust

  • Allocates team roles and accountabilities

Building Relationships

  • Solicits advice, support, championship, sponsorship and commitment for the success of PMO initiatives

  • Procures and maintains support from key stakeholders in the enterprise to evolve and advance the PMO

  • Builds both formal and informal professional networks, and extends these networks within, across and external to organizational boundaries

  • Has the ability to build and leverage third party and off-shore relationships.

Influencing Others

  • Commitment to keeping teams informed and engaged

  • Communicates ideas or positions in a persuasive manner that builds support, agreement or commitment

  • Takes actions that directly or indirectly influence others to create buy-in, gain trust and motivate actions in others, or win concessions without damaging relationships

  • Possesses the ability to facilitate win-win solutions when conflicts emerge

Results Orientation

  • Demonstrates curiosity and passion for progress

  • Sets and accomplishes challenging goals

  • Defines standards in terms of doing what is appropriate and doing it well

  • Competes resourcefully and takes calculated risks to achieve results

  • Naturally incorporates lessons learned into ways of working

Change Advocate

  • Demonstrates personal commitment to change through actions and words

  • Acts as the organizational change agent for improving PPM maturity and practices, in support of business/agency goals and strategy

  • Mobilizes others within and outside the PMO to support and enable change efforts within individual initiatives and inside business/operations units

Strategic Technology Planning

  • Develops plans that meet the architecture/technology needs of the organization

  • Incorporates business priorities, strategies, goals, OKRs, KPIs,emerging technologies, industry trends and economic viability

Business Acumen and Enterprise Knowledge

  • Solicits information on enterprise direction, goals and strategy to determine how the PMO function can add value to the organization and to customer satisfaction

  • Makes decisions and recommendations clearly linked to the organization’s strategy and financial goals, reflecting an awareness of external dynamics

Working Conditions

Travel required: 20% travel across our North American HUBs (US and Canada).

Although this role is preferred to hybrid Chicago, it is open to remote candidates.


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.

Department Information Technology

Required Experience: More than 15 years of relevant experience

Required Travel: Up to 25%

Required Education: Bachelor's degree (4-year degree)

HUB International Limited is an equal opportunity and affirmative action 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. The EEO is the Law poster and its supplement is available here at

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Hi, we’re HUB.

In a rapidly changing world, we advise businesses and individuals on how to prepare for the unexpected.

When you partner with us, you're at the center of a vast network of experts who will help you reach your goals through risk services, claims management, and compliance support.

And this gives you the peace of mind that what matters most to you will be protected — through unrelenting advocacy and tailored insurance solutions that put you in control.

About HUB International

Headquartered in Chicago, Illinois, HUB International Limited (HUB) is a leading full-service global insurance broker providing property and casualty, life and health, employee benefits, investment and risk management products and services. From offices located throughout North America, HUB’s vast network of specialists provides peace of mind on what matters most by protecting clients through unrelenting advocacy and tailored insurance solutions. For more information, please visit