Job Details

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.