Overview
Skills
Job Details
Job Title: Project Manager/Scrum Master
Onsite Requirement/Remote (Time zone?): Chicago preferred but open to remote
C/CTH/Perm + Duration: Contract, 6 months to start and ongoing
Pay Rate: $58/hr on W2 or $63/hr on 1099 as max pay rate
Job Description
Looking for a Technical Project Manager / Scrum Master to support the organization with full ownership of delivery for \ platform, a Java/AWS-based application supporting critical crew compensation processes. This role requires hands-on Agile leadership, strong technical aptitude, and the ability to manage multiple parallel workstreams with minimal oversight.
You will be responsible for driving all Agile ceremonies, maintaining delivery metrics, managing a large product backlog, and partnering closely with engineering teams to ensure timely, high-quality execution. With leadership heavily invested in advancing Agile maturity, this position is ideal for a candidate with genuine Scrum experience who is proactive, self-sufficient, and capable of independently running the Pilot Pay program with minimal supervision.
Key Responsibilities
- Serve as Scrum Master and Technical PM for the Pilot Pay platform, overseeing all day-to-day delivery activities.
- Lead Agile ceremonies including:
- Sprint planning
- Backlog refinement
- Big Room (PI) planning
- Daily standups, sprint reviews, and retrospectives
- Build and maintain Agile delivery metrics such as burndown charts, velocity tracking, and roadmap progress.
- Manage a large, active product backlog and coordinate work across multiple parallel initiatives.
- Partner closely with engineering teams in a Java + AWS environment, removing blockers and ensuring alignment on technical execution.
- Develop dashboards and reporting through Jira, Jira charts, and GitHub integrations to maintain transparency and stakeholder visibility.
- Support budget tracking and step into Planview or financial processes if needed.
- Communicate proactively with leadership, product teams, and cross-functional stakeholders.
Required Skills & Experience
- Real, practical Agile/Scrum experience, with a proven ability to run ceremonies end-to-end and drive Agile maturity.
- 7+ years as a Technical Project Manager or Scrum Master supporting software engineering teams.
- Strong understanding of Java, AWS, APIs, and modern software development practices (no coding required).
- Expertise with Jira, including roadmaps, dashboards, reporting, burndown charts, and linked GitHub workflows.
- Ability to manage multiple parallel workstreams in a fast-paced environment.
- Exceptional communication, organization, and stakeholder management skills.
- Highly self-sufficient, proactive, and capable of taking ownership with minimal supervision.