Scrum Master

Hub International Insurance • Chicago, IL

16d • Remote

About The Position

HUB International is looking for a Scrum Master to join our Agile Center of Excellence (COE), a team dedicated to scaling Agile practices across HUB’s technology organization. In this role, you’ll serve as a servant-leader and coach for one or more cross-functional delivery squads, helping teams continuously improve how they plan, deliver, and collaborate. You’ll work alongside fellow Scrum Masters and partner with Product Owners, program managers, and business stakeholders across a portfolio of technology initiatives — contributing not just at the team level, but to the broader Agile maturity of the organization.

Requirements

• 3+ years of experience as a Scrum Master supporting software delivery teams
• Certified Scrum Master (CSM) or equivalent certification; SAFe certification a plus
• Strong working knowledge of Jira — including board configuration, sprint management, and reporting
• Demonstrated curiosity about AI tools and a track record of finding practical ways to apply them in an Agile delivery context — not just awareness, but actual use
• Ability to coach teams at different Agile maturity levels without being dogmatic about the framework
• Excellent facilitation and communication skills; comfortable engaging with both delivery teams and business stakeholders
• Experience in insurance, financial services, or another regulated industry is a plus
• 2-5 years of relevant experience
• Bachelor's degree (4-year degree)

Nice To Haves

• SAFe certification a plus

Responsibilities

• Facilitate all Scrum ceremonies — sprint planning, daily standups, sprint reviews, and retrospectives — with energy and purpose
• Remove impediments and escalate blockers proactively, shielding teams from noise so they can focus on delivery
• Coach teams on Agile principles, Scrum practices, and continuous improvement; meet teams where they are and help them grow
• Track and communicate sprint health, velocity, and capacity using Jira; support teams in maintaining clean, well-groomed backlogs
• Collaborate across squads during cross-team ceremonies and dependency reviews
• Partner with Product Owners to support backlog refinement and sprint readiness
• Actively incorporate AI tools into your daily practice — from drafting retrospective summaries and surfacing impediment patterns to generating status updates and streamlining ceremony prep
• Contribute to COE initiatives: Ways of Working documentation, Agile Guild sessions, maturity assessments, and tooling improvements
• Support program-level reporting and status visibility for stakeholders and leadership

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: Mid Level