Sr. Scrum Master

Job Title: Sr. Scrum Master

Duration: Long-term

Location: Chicago, IL - Hybrid

Job Description: RESPONSIBILITIES

• Lead and coach agile delivery practices across teams using Scrum, Kanban, Lean, SAFe or similar agile methods to improve flow, transparency, predictability, and business value delivery.
• Facilitate and improve agile ceremonies and working sessions, including sprint planning, daily standups, backlog refinement, sprint reviews, retrospectives, Kanban replenishment, flow reviews, dependency discussions, and cross-team synchronization.
• Lead cross-team initiatives, coordinate delivery across multiple delivery teams when required, demonstrate project management acumen in muti-team efforts.
• Drive consistency and standardization of agile practices across teams, including working agreements, backlog readiness expectations, ceremonies, metrics, artifact hygiene, and team operating norms.
• Mentor & Supervise Scrum Masters, team facilitators, Mentor Product Owners, and delivery teams on agile values, servant leadership, continuous improvement, team self-management, and effective delivery practices.
• Partner with Product Owners to improve backlog health, prioritization, refinement quality, sprint or flow readiness, acceptance criteria quality, and alignment to business outcomes. Ability to play the product owner role when required.
• Ability to play the product owner role facilitating business stakeholder alignment and building consolidated roadmaps when required.
• Identify, escalate, and help remove team-level and organizational impediments that impact delivery progress, quality, flow, predictability, or team effectiveness.
• Establish and monitor agile delivery KPIs, including sprint predictability, throughput, cycle time, lead time, work in progress, aging work items, impediment aging, backlog readiness, team health, and delivery risk trends.
• Use agile metrics and maturity indicators to identify improvement opportunities, coach teams through behavior change, and drive measurable improvements in delivery effectiveness as well as enabling High performing teams.
• Coordinate dependencies, risks, and delivery alignment across Product, Engineering, Architecture, Quality Engineering, Security, Operations, and business stakeholders.
• Support release planning, delivery readiness, dependency management, and governance discussions while preserving agile principles, transparency, and team accountability.
• Contribute to enterprise agile maturity through agile playbooks, communities of practice, coaching patterns, maturity assessments, adoption scorecards, and standardized delivery practices.
• Support the organization s evolution toward SAFe or scaled agile practices where appropriate, including cross-team alignment, planning cadence maturity, dependency visibility, and enterprise-level agile coordination.
• Help teams adopt modern delivery practices, including DevOps, DevSecOps, Quality Engineering, CI/CD awareness, and AI-assisted agile delivery practices where applicable.

Education & Experience:

Bachelor s degree in Business, Information Technology, Computer Science, Engineering, Information Systems, or a related discipline; equivalent experience may be considered.

• 10+ years of experience in agile delivery, Scrum Master, Agile Delivery Lead, Agile Coach, project delivery, product delivery, technology delivery, team-level agile facilitator supporting technology, software, product, or enterprise delivery teams or related roles.
• Certifications such as CSM, PSM, A-CSM, CSP-SM, SAFe Scrum Master, SAFe Agilist, PMI-ACP, PMP, or equivalent agile certifications are preferred.
• Experience coaching multiple agile teams, lead/supervise Scrum Masters, supporting agile adoption, or maturing agile delivery practices across an organization.
• Experience applying Scrum, Kanban, Lean, or similar agile delivery practices in practical team environments.
• Experience with agile KPIs, DORA, team health indicators, flow metrics, maturity assessments, and continuous improvement practices.
• Experience working with Product Owners, engineering teams, architecture, quality, security, operations, and business stakeholders in an agile delivery environment.
• Experience with scaled agile practices such as SAFe, Agile Release Trains, PI planning, or cross-team dependency coordination is preferred.
• Experience with agile delivery tools such as Azure DevOps, Jira, Rally, VersionOne, ServiceNow PPM, or similar platforms is preferred.
• Experience in banking, financial services, treasury operations, capital markets, or another regulated environment is preferred

KNOWLEDGE & ABILITIES

• Deep understanding of Scrum, Kanban, Lean, agile principles, servant leadership, high performing teams, empirical delivery, and continuous improvement.
• Ability to coach teams, Product Owners, mentor/supervise Scrum Masters, and stakeholders to improve agile maturity, delivery flow, and value delivery.
• Strong facilitation skills across ceremonies, planning, retrospectives, flow reviews, dependency discussions, and cross-team alignment.
• Ability to identify impediments, manage dependencies, escalate risks, and drive resolution across teams and organizational boundaries.
• Ability to define and use agile KPIs and maturity indicators to improve predictability, transparency, consistency, and delivery outcomes.
• Strong communication, influence, situational leadership, and change enablement skills to build trust and guide teams toward shared results.
• Working knowledge of modern engineering, DevOps, DevSecOps, Quality Engineering, CI/CD, release readiness, and banking/regulatory control expectations is preferred

Advanced/Expert Competencies-

• Agile Principles: Scrum, Kanban, Lean and Similar Methods
• Servant Leadership, Supervisory/Lead scrum masters and Agile Team Coaching
• Agile Facilitation, Project management, Roadmapping and Ceremony Leadership
• Agile KPIs, Metrics, High Performing teams and Team Health Measurement
• Agile Maturity Assessment, Esitimation process and Continuous Improvement
• Agile Process Standardization and Consistency Across Teams
• Impediment Removal and Organizational Escalation
• Cross-Team Dependency Management
• Stakeholder Communication and Influence
• Conflict Resolution and Team Dynamics
• Work Planning, Prioritization, and Facilitation
• Backlog Readiness and Product Owner Partnership
• Agile Tooling: Azure DevOps, Jira, ServiceNow PPM, or Similar Platforms
• Release Planning and Delivery Readiness

Intermediate Competencies-

• Business Acumen, Product Development, Release Management and Value Delivery Alignment
• Kanban Flow Management and Work Visualization
• Scaled Agile / SAFe Readiness
• Enterprise Change Enablement and Adoption Support
• Product management / DevOps / DevSecOps / Quality Engineering
• Foundational Competencies-
• Regulatory, Audit, and Risk Awareness
• AI-Assisted Agile Delivery Practices