Location: Chicago area preferred / Hybrid / Remote - USA

Compensation: $145k-$185k base plus bonus (DOE)

Transworld Systems Inc. (TSI) is the industry-leading, tech enabled provider of accounts receivable management, healthcare revenue cycle management, loan servicing, and complementary BPO solutions. With revenues more than $500M, TSI’s customer base includes Fortune 100 corporations, financial institutions, hospitals, government organizations, and small businesses. TSI’s goal is to help customers manage their cash flow, so they can focus on growing their businesses.

As an integral part of our corporate structure, the VP, Legal is tasked with providing expert legal guidance and support to ensure our operations align with all applicable laws and regulations. This position demands a robust understanding of corporate law, regulatory compliance, contract negotiation, and risk management. Proactive problem solving and strategic thinking with exceptional communication skills and a strong ethical foundation are required. This position requires the ability to work closely with various departments, including business unit leaders, finance, human resources, information technology, and executive leadership, providing legal insights that drive informed business decisions and safeguard our organizational interests. High business acumen is essential. Must be able and willing to operate and thrive in a fast-paced environment and be adept at handling complex legal issues with a high degree of professionalism.

• Manage and lead a staff of two (2) in-house counsels regarding contract management and litigation activities
• Provide legal advice to business units to mitigate risk regarding federal and state regulations impacting operations, including FDCPA, CFPB requirements, UDAAP, FCRA, TCPA, HIPAA (when applicable), federal and state privacy and employment laws and state collection laws.
• Draft, negotiate, and execute commercial agreements, including client service contracts, vendor agreements, technology agreements, data‑sharing agreements, NDAs, and consulting contracts.
• Establish, maintain and oversee contract templates, life cycle, playbooks, and approval processes to drive efficiency and consistency.
• Partner with Compliance to develop and review policies, training programs, audits, and monitoring frameworks based on legal guidance provided.   
• Advise the CLCO regarding U.S. and non-U.S. corporate governance including bylaws, board policies, committee charters, entity formation, annual corporate filings, maintenance of corporate records and corporate structure appropriate to the US and international jurisdictions.
• Provide legal support for incident response, crisis management, and data security events.
• Evaluate insurance limits, coverage gaps, and risk‑transfer strategies and lead the investigation, reporting, and management of insurance claims, including litigation oversight and coordination with carriers.
• Oversee the litigation oversight process including: pre-litigation (claims), litigation, arbitration, and dispute resolution strategy, including management of outside counsel as needed.

• J.D. degree from an accredited law school; active bar membership in good standing.
• 8–15+ years of progressive in-house or law firm legal experience, including leadership roles; experience with collections, financial services, or similarly regulated industries preferred.
• Experience with providing legal advice on collections, privacy, employment and data security legal issues.
• Strong background in commercial contracts, corporate and international governance, and procurement contracting.
• Excellent leadership, communication, negotiation, and strategic thinking skills.
• Experience managing insurance programs and claims, domestic and cross‑border regulatory compliance is a plus.

 KNOWLEDGE AND EXPERIENCE: 

• Exceptional drafting, negotiation, and organizational skills.
• Attention to detail and willingness to learn and adapt to new platforms and technologies.
• Ability to translate complex legal and regulatory requirements into practical, business‑focused guidance for senior leadership and operational teams.
• Experience with Microsoft suite of products.
• Initiative to work independently in a project setting with members of other departments.

• Ability to work quickly and efficiently without sacrificing quality in a fast-paced environment.
• Ability to prioritize and organize work in a multitasked environment

Physical Requirements:

• Normal, corrective vision range; ability to see color and to distinguish letters, numbers and symbols
• Frequently required to sit, stand, walk, talk, hear, bend and reach
• Ability to reach with hands and arms
• Occasionally lift and/or move up to 30lbs

Work Conditions:

The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. You are acknowledging that you can perform the essential functions with or without a reasonable accommodation. The noise level in the work environment is usually moderate. The work environment is primarily indoors. The position requires little to no travel.

This job description is not an exclusive or exhaustive list of all job functions that a team member in this position may be asked to perform. Duties and responsibilities can be changed, expanded, reduced or delegated by management to meet the business needs of the company. By signing below, you are acknowledging receipt and comprehension of this job description