Technical IT Project Manager

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%.