Technical Project Manager - Java AWS Software development

Overview

Remote
$50 - $63
Contract - W2
Contract - Independent
Contract - 6 Month(s)

Skills

Agile
Amazon Web Services
GitHub
IT Project Management
JIRA
Java
Leadership
Apache Velocity
Budget
Collaboration
Communication
Dashboard
Finance
Management
Planview
Reporting
Roadmaps
Scrum
Software Development
Software Engineering
Sprint
Stakeholder Management
Supervision
Workflow

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.

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