Director Legal Services

Goodwill Industries of Southeastern Wisconsin, Inc.•Milwaukee, WI

50d

About The Position

The Director of Legal Services is a strategic, hands‑on leader who serves as the organization’s principal legal advisor and a trusted partner to senior leadership. In this role, you’ll shape and execute the legal strategy across contracts, labor and employment, compliance, real estate, and enterprise initiatives—balancing risk management with business enablement. You’ll lead complex litigation and regulatory matters, guide executives through high‑stakes decisions, and translate evolving legal and regulatory requirements into practical, actionable solutions. As a department leader, you’ll build and develop high‑performing legal talent, design scalable systems and processes, and drive long‑term initiatives that strengthen compliance, operational excellence, and organizational impact, all while advancing equity, inclusion, and community engagement. The Director Legal Services manages legal matters for the organization, including contracts, labor and employment, compliance, real estate, and event documentation. This role works closely with Retail and Operations teams to support business needs and reduce risk. Develops long- and short-term business strategies (3-5 years) and oversees implementation for Legal department. Is heavily involved in developing department standard operating procedures. Forecasts and plans annual operating and capital budget, implements cost-savings measures. Maintains and adjusts operating budget, manages expenses based on changes in internal or external factors, and communicates budgetary performance. Typically works on projects and initiatives that span 2-5 years. Responsible for integration of systems, systems metrics, and analysis.

Requirements

Juris Doctorate Degree from an ABA accredited law school and be in current good standing with a state bar association.
Minimum of 8 years experience - legal or regulatory experience with direct client contact.
License to practice law in WI and/or IL.
Capacity to cope with complex situations through deliberate analysis and planning.
Experience working with diverse communities and a demonstrated commitment to equity and inclusion.

Responsibilities

Serve as the principal legal advisor, providing executive-ready legal guidance to senior leadership and ensuring alignment with the strategic direction set by the external fractional General Counsel and Chief People & Compliance Officer.
Lead and provide enterprise-wide counsel on labor, employment, and workplace regulatory issues, ensuring guidance is timely, practical, and actionable for Business Units.
Translate complex nonprofit and corporate legal implications into clear, actionable recommendations for organizational leaders.
Direct litigation strategy and regulatory complaint response across forums, , and risk-balanced outcomes through attorney teams.
Oversee high-risk separations and regulatory inquiries (service termination, severance agreements, DOL/DWD, EEOC), providing clear positions and defensible documentation.
Consult and provide support during dispute resolution and settlements to protect the organization s interests.
Proactively identify and assess legal and compliance risks, anticipating issues, tracking organizational developments, and recommending risk-mitigating actions.
Translate legislative and governance changes into policy and procedure updates, recommending and implementing solutions that ensure continuous compliance.
Oversee the preparation, review, and finalization of event chronologies and formal findings summaries, ensuring that case documentation and recommendations are thorough, accurate, and support sound legal decision-making at the executive level.
Communicate executive-level summaries and reports on legal matters, ensuring clarity, accuracy, and actionable recommendations to senior leadership and the broader legal and compliance leadership team.
Partner with Procurement and Finance on contract lifecycle management, (ensuring compliance with enterprise policy and risk thresholds.
Consult with Finance on corporate transactions and commercial contracting (including licenses, RFPs, NDAs, tax-exempt counseling) by recommending standards, templates, and guardrails aligned to business objectives.
Supervise legal aspects of company real estate transactions, including documentation, regulatory considerations, and alignment with organizational objectives.
Lead and develop in-house counsel and legal operations staff, calibrating workloads, quality expectations, and professional growth to deliver consistent, high-standard legal services.
Leading and Developing Talent: Manages organizational design for area of responsibility and directs talent planning, hiring, development and training of staff. May participate in succession planning discussions. Networks and sources for positions throughout the organization.
Project and Change Management: Serves as project owner for high complexity department, cross-functional or multi-location projects and improvement initiatives. Set project direction including project scope, timeline and resources. Accountable for making decisions and project success. Manages change through effective planning, communication and coaching. Builds and participates in leadership coalition supporting and implementing organizational change.
Community Engagement: Actively engages with community partners and links activities to business performance.
Responsible for completing other duties/responsibilities as assigned.