IT Sr. Scrum Master/Project Manager
Product, IT, Operations
Remote
Senior Scrum Master / Program Manager (Telematics Portfolio)
Location: Remote (EST Preferred)
Duration: 6-Month Contract (Potential Extension and Contract-to-Hire Opportunity)
About the Role
Our client is seeking an experienced Senior Scrum Master / Program Manager to support a high-visibility Telematics Portfolio focused on innovative initiatives including fleet telematics, accident assistance, and connected vehicle technologies.
This role is ideal for a delivery-focused Agile leader who excels at driving complex, cross-functional programs, managing dependencies across multiple teams, and partnering with technical and business stakeholders to ensure successful outcomes. The successful candidate will operate at the portfolio level, helping improve delivery predictability, transparency, and execution across multiple Agile teams.
What You'll Do
- Lead planning, coordination, execution, and delivery of large-scale cross-functional initiatives.
- Facilitate portfolio-level Agile ceremonies, including PI Planning, mid-PI reviews, and PI closeout activities.
- Drive alignment across Product, Engineering, Business, and Portfolio stakeholders.
- Manage and proactively mitigate risks, blockers, dependencies, and delivery challenges.
- Facilitate Scrum of Scrums and support dependency management across multiple Agile teams.
- Develop and maintain initiative roadmaps, milestone plans, RAID logs, and delivery dashboards.
- Monitor delivery metrics and provide actionable insights to improve execution and predictability.
- Partner with Engineering Managers, Product Owners, and portfolio leadership to communicate delivery status and risks.
- Establish and maintain Jira standards, workflows, dashboards, and reporting to enhance visibility and support portfolio governance.
- Coach teams on Agile best practices, continuous improvement, accountability, and effective delivery planning.
- Support organizational change initiatives through structured communication, planning, and stakeholder engagement.
Required Qualifications
- Bachelor's degree in Business, Computer Science, Information Technology, or a related field.
- 5+ years of experience as a Scrum Master, Program Manager, Project Manager, or Agile Delivery Leader within technology organizations.
- Experience leading complex initiatives across multiple Agile teams and functional domains.
- Strong understanding of Agile frameworks, Lean principles, and scaled delivery practices.
- Demonstrated experience managing risks, dependencies, stakeholder communications, and delivery governance.
- Strong knowledge of software development and technology delivery processes.
- Advanced Jira expertise, including dashboard creation, reporting, workflow management, dependency tracking, and portfolio-level visibility.
- Proven ability to partner with technical leaders and translate complex delivery information into actionable plans and executive communications.
- Excellent communication, facilitation, and stakeholder management skills.
Preferred Qualifications
- Experience working in Insurance, FinTech, or Technology organizations.
- Knowledge of telematics products, connected vehicle platforms, fleet management solutions, or related technologies.
- Experience supporting SAFe or other scaled Agile environments.
- Advanced Agile certifications such as:
- PSM II
- ICAgile Agile Team Facilitation (ICP-ATF)
- ICAgile Agile Coaching (ICP-ACC)
- SAFe Certifications