Contract to Hire - Senior Technical Project Manager / Delivery Lead

recruit22 LLC

Chicago, IL(remote)

JOB DETAILS
SKILLS
Acceptance Testing, Agile Programming Methodologies, Analysis Skills, Artificial Intelligence (AI), Atlassian JIRA, Budget Management, Computer Science, Consulting, Cross-Functional, Data Management, Forecasting, Healthcare, Leadership, Management of Information Systems/Technology (MIS), Matrix Management, Microsoft Excel, Microsoft PowerPoint, Microsoft Visio, Microsoft Word, Organizational Skills, Program Planning, Project Execution, Project Tracking, Project/Program Management, Quality Management, Regulatory Compliance, Reliability Testing, Resource Management, Risk, Risk Management, Software Development Lifecycle (SDLC), Software Engineering, Status Reports, Technical Leadership, Test Data, Test Plan/Schedule, Test Strategy, Use Cases
LOCATION
Chicago, IL(remote)
POSTED
5 days ago

Senior Technical Project Manager / Delivery Lead

Remote - USA
C2H - No Sponsorship Provided

Overview

An innovative, solutions-oriented Senior Technical Project Manager / Delivery Lead is needed with strong analytical, technical, and program management capabilities. This role requires a blend of rigorous delivery leadership, technical fluency, and expertise in Jira to drive visibility, coordination, and execution across complex initiatives.

A key responsibility will be leading an enterprise-wide program to stabilize and mature UAT and DEV environments to improve quality and development efficiency, including support for AI-assisted development, testing capabilities, and expanded use-case coverage. Success will depend on strong coordination, integration, and execution across multiple ongoing efforts.

The position is responsible for driving planning, execution, and day-to-day program oversight across the full lifecycle, partnering closely with engineering, architecture, and business teams to deliver scalable, high-quality outcomes. The successful candidate will improve delivery outcomes through proactive leadership and strategic contributions beyond traditional project management activities.


Areas of Responsibility

Program & Delivery Leadership

  • Lead large-scale, multi-year programs across complex enterprise environments from initiation through production rollout.
  • Drive execution of environment and test data strategies, aligning 10+ teams on priorities, sequencing, and shared outcomes while ensuring data privacy and compliance requirements are met.
  • Coordinate and integrate partially completed work into a unified, executable roadmap with clear milestones and ownership.
  • Establish and enforce accountability structures across workstreams, including teams with shared resources and competing priorities.
  • Manage interdependencies, risks, and blockers across multiple teams while maintaining engagement from senior leadership.

Project Oversight & Execution

  • Own the end-to-end integrated program plan, ensuring alignment across all supporting workstreams.
  • Serve as the primary liaison between technical and business stakeholders, translating complex system, environment, and testing challenges into actionable plans.
  • Navigate highly matrixed organizations while maintaining accountability for timelines, deliverables, and outcomes.
  • Provide transparent communication through executive reporting, program reviews, and stakeholder updates.
  • Drive environment readiness and operational stability, ensuring testing environments meet reliability standards before additional enhancement initiatives begin.
  • Maintain key program artifacts, including:
    • Integrated Program Plan
    • Weekly Status Reports
    • Milestone Tracking and Dependency Mapping
    • Risk and Issue Register

Financial & Resource Management

  • Forecast and manage resource allocations across multiple teams, ensuring alignment with program priorities.
  • Track and manage program budgets with strong financial discipline.

Required Qualifications

  • 8+ years of Project or Program Management experience delivering cross-functional initiatives.
  • 5+ years leading large-scale, multi-team infrastructure or platform programs.
  • 3+ years leading projects focused on environments, test data management, and data privacy considerations.
  • Experience supporting AI-driven development efficiencies is a strong plus.
  • Proven experience driving environment stabilization, platform maturity, or large-scale integration efforts.
  • Strong understanding of Agile methodologies, SDLC frameworks, and enterprise delivery governance.
  • Expertise with Jira for planning, tracking, and reporting at scale.
  • Healthcare or other highly regulated industry experience preferred.
  • Proficient with Microsoft Word, Excel, PowerPoint, and Visio.
  • Experience with Smartsheet is a plus.

Education

Bachelor's degree in Software Engineering, IT Management, Computer Science, or a related technical discipline.

About the Company

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recruit22 LLC