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.