Senior Project Manager

HUB International • Chicago, IL

13d • $120,000 - $140,000 • Remote

About The Position

HUB International’s Technology and Operations PMO is seeking a Senior Project Manager to join a high-performing team supporting enterprise technology initiatives across the organization. This role is designed for an experienced delivery professional ready to lead complex, cross-functional projects, serve as a trusted partner to senior stakeholders, and actively contribute to the maturation of PMO delivery standards and team capabilities. The successful candidate will bring a strong track record of leading high-stakes technology initiatives, a proactive approach to risk management, and the leadership presence to influence across organizational levels. They will partner closely with TechOps delivery teams, change management, and business stakeholders to drive meaningful outcomes aligned to HUB’s strategic objectives.

Requirements

• Bachelor’s degree in Computer Science, Information Systems, Business Administration, or a related field or commensurate experience
• 8+ years of experience in a project delivery role, including demonstrated experience leading complex, multi-workstream projects simultaneously
• Deep working knowledge of waterfall delivery methodology; practical experience with agile practices and hybrid delivery approaches
• Proven ability to identify, structure, and manage project risk in a disciplined, proactive manner — including executive-level escalation
• Ability to manage multiple concurrent projects with strong attention to detail, follow-through, and composure under pressure
• Executive presence and communication skills, with the ability to influence stakeholders, facilitate decisions, and tailor messaging across organizational levels
• Service-oriented mindset with a strong sense of accountability to business needs, project teams, and end-users
• Collaborative, solutions-oriented approach with the confidence to raise issues constructively and lead through ambiguity

Nice To Haves

• PMP or equivalent Agile certification
• Experience working within a formal PMO environment, including contribution to standards or governance frameworks
• Background in business analysis, organizational change management, or process improvement
• Insurance industry experience

Responsibilities

• Lead end-to-end delivery of complex, cross-functional IT-enabled projects from initiation through close, often spanning multiple teams or workstreams
• Define and maintain robust project plans, including scope, schedule, dependencies, risks, and issues across concurrent initiatives
• Proactively identify, assess, and manage risks throughout the delivery lifecycle; maintain structured risk registers, ensure clear ownership, and escalate exposure with timeliness and transparency
• Serve as a primary point of contact for senior stakeholders and executive sponsors, delivering clear, confident status communications, decision packages, and escalation recommendations
• Anticipate stakeholder needs and translate complex delivery dynamics into actionable, audience-appropriate messaging
• Model a service mindset — building trusted relationships with delivery teams and business partners, prioritizing their success, and fostering a collaborative delivery environment
• Coordinate across vendors, IT Operations, and organizational change management resources to ensure integrated, well-sequenced execution and sustainable adoption
• Provide informal coaching and peer support to Project Managers on delivery practices, risk discipline, and stakeholder engagement
• Contribute actively to the development and continuous improvement of PMO delivery standards, methodologies, tooling, and governance frameworks
• Support portfolio-level visibility by maintaining high-quality project data and participating in PMO governance cadences

Benefits

• 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
• annual bonuses
• equity
• commissions

What This Job Offers

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