Scrum Master Job at Squaremouth, Chicago, IL

  • Squaremouth
  • Chicago, IL

Job Description

Scrum Master

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.

What You'll Do

  • 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

What We're Looking For

  • 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

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 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.

The expected salary range for this position is $95,000 to $125,000 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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