Top Senior Legal Jobs in Chicago, IL

Leads litigation, legal policy, and advocacy strategy affecting pharmaceutical innovation, drug pricing, access, and reimbursement. Advises senior leaders and business functions, manages complex disputes and government investigations, oversees outside counsel and budgets, engages government and industry stakeholders, and monitors legal and regulatory developments. Requires substantial trial and appellate litigation experience, policy judgment, executive presence, and collaboration across a highly regulated pharmaceutical environment.

Leads legal pricing strategy, matter budgeting, alternative fee arrangements, and external law firm negotiations. Advises senior legal and business stakeholders using financial and matter-performance insights, evaluates AI impacts on pricing and service delivery, and drives adoption of AI-enabled pricing tools. Collaborates across Legal, Finance, Legal Technology, and Procurement on transformation initiatives while delivering training, change management, market analysis, governance, and executive-ready recommendations.

Provide business-oriented legal guidance on U.S. broker-dealer regulation, digital assets, payments, privacy, product launches, marketing, onboarding, regulatory engagement, agreements, policies, and disputes. Monitor SEC, FINRA, CFTC, FinCEN, and OFAC developments; conduct legal research; advise cross-functional teams; and manage litigation, arbitration, outside counsel, claims, and discovery.

Leads Hazel Health’s in-house legal and enterprise compliance functions. Advises on healthcare regulation, telehealth, corporate governance, contracts, privacy, security, employment, risk, and investigations. Builds legal operating systems, templates, playbooks, compliance controls, and matter-management processes while reducing outside-counsel spend. Manages specialized counsel for complex matters and provides candid guidance to executives and the Board.

Administer and optimize contract lifecycle management, AI-assisted legal review, eBilling, and outside counsel systems. Configure workflows, templates, clause libraries, approval routing, integrations, reporting, and user training. Develop legal technology processes, dashboards, KPIs, prompt libraries, and knowledge repositories; support AI governance and cross-functional enablement. Improve contract turnaround times, system adoption, data integrity, compliance, invoice workflows, billing guideline adherence, accrual reporting, and legal spend analytics.

Review and edit deposition transcripts for grammar, formatting, legal accuracy, consistency, confidentiality, and compliance with company and industry standards. Communicate effectively with internal teams, manage multiple assignments independently, and deliver polished transcripts reliably and on time as a remote 1099 contractor. Familiarity with AI transcription platforms is beneficial, and training is provided on proprietary software.

Provide hands-on legal and compliance support: draft, review, negotiate, and manage contracts; maintain corporate governance and entity records; support FINRA/SEC/MSRB compliance, regulatory exams, and legal operations technology and workflows.

Serve as Freshpaint’s first in-house legal leader, advising the CEO and cross-functional teams on commercial contracting, privacy, data protection, compliance, employment, corporate governance, financing, equity, and intellectual property. Build scalable legal templates, playbooks, workflows, and risk-management processes; negotiate customer, vendor, partner, and technology agreements; embed privacy-by-design practices; and manage outside counsel and legal spend.

Oversee and finalize legal documents governing data sharing between Healthcare Fraud Prevention Partnership members and a trusted third party. Collaborate with CMS, HFPP leadership, partner engagement teams, and private payer partners on agreements, compliance, and negotiations. Present to management, support partner relationships, and ensure legal requirements are met for data governance and sharing.

Provide legal advice on technology and procurement matters, focusing on AI, cloud, SaaS, licensing, distributed ledger, and product development. Draft and update templates, negotiate complex technology agreements, support cross-functional teams and governance committees, and advise on regulatory developments affecting technology procurement across multiple jurisdictions.

Provide commercial transactional legal support for large, complex merchant and partner deals globally. Negotiate and draft multinational agreements, advise sales and cross-functional teams on payments, licensing, and regulatory risk, manage deal closings, ensure compliance, escalate high-stakes issues, and develop risk management frameworks to protect PayPal's legal interests.

Provide strategic legal counsel to global and U.S. teams on commercial and strategic agreements, corporate governance, compliance, intellectual property, privacy, security, and product matters. Negotiate customer and vendor contracts, develop templates and playbooks, manage contract and governance systems, support M&A and fundraising, and coordinate outside counsel. Advise business leaders, review marketing and product materials, and partner with compliance teams to address legal and regulatory requirements.

Provide legal guidance on global payment processing, fintech regulation, money movement, licensing, compliance, and digital innovation. Draft and negotiate agreements with payment providers, banks, card networks, vendors, and partners. Advise on KYC/KYB, AML, sanctions, entity structuring, market expansion, chargebacks, settlements, reserves, and emerging technologies. Collaborate with product, technology, operations, and management teams to launch compliant payment products and address legal risks.

Build and run legal operations: implement contract lifecycle and document management systems, design intake/process workflows, support compliance (AML/KYC, sanctions, regulatory filings), manage corporate governance and entity administration, liaise with outside counsel, and help develop AI-enabled legal workflows alongside the General Counsel.

Lead a remote library and research team delivering legal, regulatory, and competitive research to attorneys. Oversee client relationships, implement research workflows and tools, govern digital resources, champion adoption of AI-powered legal technologies, and manage projects, budgets, vendors, and staff development to ensure timely, accurate insights.

Provide legal guidance on a variety of commercial and regulatory matters, with a focus on drug information and healthcare solutions. Manage outside counsel and counsel on compliance with HIPAA, GDPR, and healthcare laws.

Manage a litigation portfolio focused on single-plaintiff consumer finance matters, including FCRA, FDCPA, TCPA, and state consumer protection claims. Supervise outside counsel, support regulatory investigations, conduct legal research, advise business stakeholders on litigation and compliance risks, oversee subpoenas and legal holds, develop risk mitigation strategies, monitor litigation metrics, and provide training. The role requires practical guidance across student loan servicing operations and evolving federal and state legal requirements.

This role involves delivering high quality legal research services and coordinating with the Research & Information Services team to support client engagements.

The Legal Operations Director will streamline legal processes, oversee legal technology, and enhance operational performance through strategic initiatives and metrics analysis.

The Legal Assistant will support lawyers in a corporate legal team by managing tasks, ensuring organization, and preparing documents. Responsibilities include administrative tasks and legal document preparation.

Leads commercial, privacy, and product legal functions for a cloud technology company. Drafts and negotiates complex SaaS, partnership, reseller, and technology agreements; advises on global privacy, data protection, AI, intellectual property, and product development issues; develops contracting processes and playbooks; partners with cross-functional teams; and manages, mentors, and develops legal professionals.

Provide strategic employment law advice across multiple jurisdictions; lead complex advisory and contentious employee matters; implement scalable legal solutions; drive cross-functional initiatives; build team knowledge resources and governance; manage external local counsel and oversee complex employment projects.

Manage and scale a team of Legal Engineer/Product Specialists to drive customer adoption, retention, and expansion. Engage with strategic accounts, coach through complex implementations, build playbooks and scalable processes, partner cross-functionally to influence product roadmap, and measure team performance to ensure customer value realization.

Author and verify rigorous multiple-choice legal assessment items for AI benchmarks across multiple legal specialties. Create clear, self-contained questions with one correct answer and nine plausible distractors, classify difficulty, provide structured solution explanations and references, and review/edit questions for legal accuracy and clarity. Work remotely, asynchronously, as an independent contractor, committing 10+ hours weekly.

Provide strategic employment law advice across the employee lifecycle, lead internal investigations, manage employment litigation and agency charges, support regulatory and policy compliance, advise on workforce transformations and executive employment matters, deliver training, and partner with HR, Compliance, and senior leaders to mitigate employment-related risk for a large, complex organization.