Payments Project Manager (Chicago)

Job Description A large retainer is seeking a Senior Project Manager to lead complex Payment Systems initiatives across our retail and membership businesses.

This role is hands-on:

you will own requirements end-to-end, drive cross-functional execution teams, and translate ambiguous business needs into clearly scoped, well-documented deliverables. The ideal candidate is a self-starter who thrives once given direction, picks up new domains quickly, and is comfortable working alongside technical teams to keep delivery on track. This position blends classic project management discipline with modern AI-augmented workflows. You will be expected to use AI tooling to accelerate requirements gathering, documentation, status reporting, and stakeholder communication — setting the standard for how PM work gets done across the organization.

Pay Rate:

$55-75/hour We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.

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https://insightglobal.com/workforce-privacy-policy/. Skills and Requirements Key Responsibilities

Requirements Leadership:

Lead requirements gathering sessions with business and technical stakeholders. Capture, organize, and document functional, technical, operational, and compliance requirements with a level of clarity that execution teams can build directly from.

Payment Systems Delivery:

Manage end-to-end implementation of payment systems initiatives — including POS integrations, payment gateways, tokenization, PCI-aligned workflows, refunds/chargebacks, and reconciliation — across retail dealership and/or membership service environments.

Execution & Drive:

Take direction and run with it. Identify gaps, ask the right questions, and move work forward without waiting to be told. Anticipate blockers and remove them before they impact the schedule.

Technical Fluency:

Engage credibly with engineering, integrations, and infrastructure teams. Understand enough about APIs, data flows, system integrations, and release processes to challenge assumptions, sequence work correctly, and keep delivery teams unblocked.

AI-Augmented PM Practice:

Apply AI tooling (Claude, copilots, custom skills) across the PM lifecycle — charters, requirements, RAID logs, RACI matrices, status reports, meeting summaries, and stakeholder communications. Continuously refine prompts and workflows to improve speed and quality.

Stakeholder Communication:

Produce executive-level status reports, decision memos, and steering committee materials. Tailor communication to the audience — from engineering standups to C-suite updates.

Governance & Standards:

Operate within PMI-aligned project management standards. Maintain charters, schedules, risk/issue logs, change controls, and decision records throughout the project lifecycle.

Cross-Functional Coordination:

Coordinate across IT, Finance, Accounting, Operations, Loss Prevention, Legal/Compliance, and external vendors/payment processors to deliver integrated outcomes.

• PMP, PMI-ACP, or equivalent certification.
• Experience with PCI DSS-aligned project work and controls.
• Prior experience in RV, automotive, or specialty retail/dealership environments.
• Familiarity with ERP, CRM, and accounting/reconciliation systems as they intersect with payment flows.
• Experience building reusable PM templates, skills, or playbooks for an organization.