Carol Stream, Illinois, United States

Technical IT Project Manager - Hybrid Chicago

 Job Description:

Project Manager Technology Programs (OSG)

Location: Hybrid Greater Chicago Area
Duration: 612 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. Were 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.

Qualifications

  • 510 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 Role

  • Direct 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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