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About the role

Technical IT Project Manager - Hybrid Chicago Carol Stream, Illinois, United States Project Manager Technology Programs (OSG)
Location: Hybrid Greater Chicago Area Duration: 6–12 months (extension likely) Engagement: Contract / Contract-to-Hire
Overview: OSG is modernizing its technology landscape across multiple verticals including finance, government, and HOA client platforms while consolidating legacy applications and improving client onboarding speed. We’re seeking a hands-on Project Manager to drive execution across migrations, integrations, and digital enablement programs. The ideal candidate is process-driven yet adaptable, able to bring structure to complex initiatives while building trust across functional teams.
Key Responsibilities:
  • Lead planning and delivery of projects spanning migrations, client onboarding, and integration initiatives (Helios, Oracle, Infoslips, Quadient, DVPP).Partner cross-functionally with IT, Product, Operations, and Compliance to define scope, milestones, and interdependencies.
  • Develop detailed project schedules, RAID logs, and stakeholder reports to ensure transparency and accountability.
  • Facilitate daily stand-ups, sprint reviews, and steering committee updates as needed.
  • Identify risks and drive issue resolution across onsite and offshore teams.
  • Collaborate with business sponsors to translate technical workstreams into business outcomes.
  • Support PMO standardization and documentation for repeatable success.
  • Qualifications5–10 years of project management experience delivering cross-functional IT or product initiatives.
  • Proven success managing migrations, platform integrations, or ERP/CRM implementations (e.g., Oracle, D365, Salesforce, or similar).Familiarity with Agile/Hybrid delivery models and experience coordinating offshore teams.
  • Excellent communication and stakeholder management skills; able to bridge technical and business language.
  • PMP or equivalent experience preferred.
  • Exposure to AI, automation, or analytics programs a plus (OSG has an AI adoption initiative).Soft Skills
  • Operates with radical transparency and accountability.
  • Naturally builds alignment across departments.
  • Thrives in fast-paced, changing environments with multiple moving parts.
  • Success Metrics
  • On-time project delivery (±10% variance to baseline).Improved cross-department communication (reduction in rework and UAT failures).Stakeholder satisfaction 90%.Salary Package: $150,000.00 - 165,000.00 (US Dollar)
  • Package Details
  • Engagement Type: Contract or Contract-to-Hire (initial 6–12 months; likely extension through multi-phase migration and onboarding programs).Location & Schedule:
Hybrid: primary office in Greater Chicago area. Expected 2–3 days onsite weekly during key program phases; flexibility outside of delivery milestones. Core hours: 8:30 AM – 5:00 PM CST (cross-functional collaboration with East Coast and offshore teams).
Compensation Range: $80–$90/hour (DOE).Conversion target: $150K–$165K annualized base plus performance incentives if converted to full-time.
Benefits: (via MCLI):Health, dental, and vision coverage.401(k) with company match after 6 months. PTO accrual for long-term contracts (>6 months).Continuous education & certification reimbursement (PMP, Agile, AI fundamentals).Why This RoleDirect exposure to OSG's 2026 transformation roadmap — migrations, onboarding, AI, and integrations. Chance to shape the PMO rebuild and cross-department delivery model. High visibility to senior leadership (reporting to VP IT and collaborating with Product, Ops, and Compliance).“Day-one impact” opportunity in an organization modernizing its entire tech stack.

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JOB OVERVIEW

Salary

$150,000 per year

Experience level

Lead

Location

Chicago, IL

Occupation

Project Management Specialists

Industry

Computer Systems Design Services

Posted

3 days ago

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