Technical IT Project Manager - Hybrid Chicago

Job Description

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%.