Senior Scrum Master

Life in Pittsburgh; Pittsburgh (Allegheny County); Hybrid; USD 104,000 - 127,000; Full time

Benefits offered by this job

Bonus

Job summary

Pittsburgh Tomorrow is seeking a Senior Scrum Lead for a 3-6 month contract-to-hire engagement. The role begins with remote work during the contract period and shifts to a hybrid arrangement once permanent.

You will lead Digital Services teams spanning underwriting, policy servicing, claims, and distribution to drive delivery excellence and remove impediments. You will coach Agile practices, facilitate Scrum ceremonies, collaborate with Product Owners and stakeholders, manage backlogs, and

Qualifications

• CSM/PSM/SAFe Scrum Master or equivalent preferred
• 5+ years as Scrum Master / Agile delivery / Project Management
• Advanced Jira: Initiatives/Epics/Stories, boards, filters, JQL, dashboards, burndown/velocity/CFD reports
• Confluence and Advanced Roadmaps / Jira Align preferred
• Experience in Insurance - Life & Annuities, Financial Services, or other regulated industry
• Strong facilitation, stakeholder management, and coaching skills

Responsibilities

• Facilitate Scrum ceremonies and coach teams on Agile / Scrum / Lean best practices
• Foster self-organization, accountability, and continuous improvement
• Monitor team health and remove delivery bottlenecks
• Serve as liaison between tech teams and business stakeholders
• Align delivery plans to business objectives and manage competing priorities
• Communicate progress, risks, and dependencies to leadership
• Partner with Product Owners to maintain healthy, prioritized backlogs
• Manage risks, blockers, and cross-team dependencies
• Provide transparent visibility into schedules, milestones, and capacity
• Lead release planning and ensure regulatory/compliance needs are in backlog and release plans
• Track velocity, predictability, cycle time via Jira dashboards
• Drive retros and process improvements to increase efficiency and quality

Skills

Scrum Master

Agile delivery

Stakeholder management

Coaching

Tools

Jira

Confluence

Jira Align

Advanced Roadmaps

Job description

We're searching for a Sr Scrum Lead. This will be a 3-6 month contract to hire with salary up to 115K plus bonus. Remote during contract, then hybrid once permanent

Senior servant leader for Digital Services teams supporting new business, underwriting, policy servicing, claims, and distribution. You will improve team effectiveness, remove impediments, and align delivery across Technology and business stakeholders in Sales, Operations, Claims, and Marketing.

What You'll Do:

Agile Leadership

• Facilitate all Scrum ceremonies and coach teams on Agile / Scrum / Lean best practices
• Foster self-organization, accountability, and continuous improvement
• Monitor team health and remove delivery bottlenecks

Stakeholder Partnership

• Serve as liaison between tech teams and business stakeholders
• Align delivery plans to business objectives and manage competing priorities
• Communicate progress, risks, and dependencies to leadership

Delivery & Execution

• Partner with Product Owners to maintain healthy, prioritized backlogs
• Manage risks, blockers, and cross-team dependencies
• Provide transparent visibility into schedules, milestones, and capacity
• Lead release planning and ensure regulatory/compliance needs are in backlog and release plans

Continuous Improvement

• Track velocity, predictability, cycle time via Jira dashboards
• Drive retros and process improvements to increase efficiency and quality

Qualifications:

• CSM, PSM, SAFe Scrum Master or equivalent preferred
• 5+ years as Scrum Master / Agile delivery / Project Management
• Advanced Jira: Initiatives/Epics/Stories, boards, filters, JQL, dashboards, burndown/velocity/CFD reports
• Confluence and Advanced Roadmaps / Jira Align preferred
• Experience in Insurance - Life & Annuities, Financial Services, or other regulated industry
• Strong facilitation, stakeholder management, and coaching skills