Top Senior Legal Jobs in Madison, WI

Provides senior legal counsel on AI, product development, marketing, legal technology, technology transactions, and emerging regulations. Advises Product, Engineering, Marketing, Partner, Customer Success, and Strategy teams; drafts policies and agreement terms; negotiates vendor, open-source, collaboration, and customer agreements; supports product launches and go-to-market strategies; and translates complex AI laws into practical business guidance.

Evaluate AI-generated legal and compliance work products, including documents, spreadsheets, and slide decks, against domain-specific quality rubrics. Assess accuracy, rigor, factual correctness, aesthetics, and presentation quality, then provide clear, structured written feedback. This is a fully remote, hourly independent-contractor engagement with flexible scheduling and weekly payments.

Manage Life360’s patent and trademark portfolios, including prosecution, enforcement, and outside counsel relationships. Advise on intellectual property matters involving patents, trademarks, trade secrets, licensing, open-source software, product development, and commercial transactions. Draft and negotiate IP-related agreements, support M&A due diligence, review marketing materials for compliance, and counsel cross-functional teams on strategic IP risks and opportunities.

Owns the end-to-end contract and legal document lifecycle, including maintaining MSAs and templates, redlining routine agreements, managing document control and data rooms, coordinating due diligence, tracking renewals, and supporting contract execution. Drafts investor, equity, trademark, and corporate filing documents while serving as an internal legal and paralegal resource. Partners with Finance, Compliance, Sales, People Operations, leadership, and outside counsel, escalating higher-risk legal matters as needed.

Own and operate Arctic Wolf’s global privacy program across multiple jurisdictions. Develop privacy policies, data maps, assessments, and compliance processes; advise Product and Engineering on privacy by design; support incident response, data subject requests, commercial agreements, and regulatory inquiries. Manage outside counsel and privacy vendors while providing practical guidance, training, and scalable playbooks.

Leads legal operations, corporate governance, entity management, securities compliance, transaction support, contract workflows, legal technology, and compliance initiatives. Oversees legal operations teams, Board and committee materials, corporate records, filings, document systems, and process improvements. Partners with executive leadership, Finance, HR, and external counsel to build scalable legal department processes.

Advise ClassPass and Playlist on product compliance throughout the development lifecycle, focusing on consumer protection, AI regulation, privacy, data protection, marketing, and platform regulations. Partner with Product, Design, Engineering, Security, sales, marketing, and operations teams; monitor global regulatory developments; maintain privacy records and assessments; draft policies and agreements; support negotiations, M&A, training, and other legal projects.

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.

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 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.

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.

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.

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

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.

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.

Manage construction defect litigation and complex third-party claim files, perform coverage analysis, manage outside counsel, conduct legal research and file audits, advise on negotiations/mediations, recommend reserves/payments, and support policy form review and claims reporting to senior management.

Provide U.S. regulatory legal counsel on crypto and financial matters, coordinate with agencies and internal teams on investigations, enforcement, AML/sanctions compliance, remediation, and regulatory filings, and advise on evolving U.S. regulatory developments affecting the business.

Provide commercial legal support for sales, finance, product, and engineering: draft, review, and negotiate SaaS, partner, vendor, and NDAs; identify data, IP, and privacy risks; build templates and playbooks; use AI-assisted contract tools to streamline workflows; coordinate with data acquisition, product, and privacy teams.

Provide senior-level legal expertise to design, evaluate, and benchmark AI systems for legal tasks. Review AI outputs, create task specifications and reference solutions, develop evaluation frameworks and scoring guidelines, and give structured feedback. Collaborate with researchers, engineers, and program teams to translate professional legal judgment into consistent evaluation standards.

Own commercial contracting, privacy and data-protection (GDPR, CCPA/CPRA, HIPAA) programs, corporate governance, IP/open-source policy, and telecom/AI regulatory posture. Be the in-house legal function: build playbooks, support Sales/Product/Engineering, and manage outside counsel to keep deals and product shipping moving quickly.

Lead the legal function: own commercial contracting, stand up privacy and data-protection programs, advise Sales/Finance/Product/Engineering, manage corporate governance and equity matters, set IP/open-source and AI governance posture, and manage outside counsel while building playbooks to enable fast business operations.

Provide pragmatic, business-focused legal advice and lead commercial contracting for North America. Negotiate customer/vendor agreements, support M&A diligence, manage pre-litigation disputes, develop contract templates and processes, partner with commercial teams, and oversee litigation strategy while improving legal operations and compliance.

Provide in-house legal counsel for procurement, supply chain, logistics, operations and real estate across North America. Draft, review, and negotiate vendor and service agreements, manage vendor disputes and pre-litigation issues, support M&A due diligence, develop contracting templates and playbooks, and advise on operational risk, compliance, and strategic transformation initiatives.