Head of Labor Relations

Hybrid is 3x a week on site in Portland, Oregon

Our client is a dynamic organization with over 800 employees in Portland, Oregon, recognized for its collaborative, values-driven, and trailblazing workforce committed to its communities, environment, and social equity. The organization builds shared prosperity through travel, trade, and economic development, driving initiatives that strengthen the regional economy and support quality jobs, multigenerational wealth, and equitable access to markets.

Our client is seeking a seasoned labor relations leader who can operate as both a strategic thought partner, advisor and trusted practitioner. Reporting to the Head of Human Resources, this role provides enterprise-level leadership across collective bargaining, contract administration, dispute resolution, and labor management partnerships.

This leader will bring sound judgment, credibility, and calm leadership to a complex union environment, balancing organizational priorities, legal obligations, and long-term workforce stability. Success requires the ability to influence at the executive level while remaining grounded in day-to-day labor realities.

Enterprise Labor Relations Strategy

• Develop and lead a coordinated, enterprise-wide labor relations strategy that promotes short-and long-term planning and coherence across multiple collective bargaining agreements.
• Plan across bargaining cycles to establish disciplined approaches to preparation, sequencing, and prioritization that support predictable labor outcomes.

Collective Bargaining & Negotiations

• Serve as the lead negotiator and management spokesperson for collective bargaining agreements, including development of bargaining strategy, proposals, and settlement frameworks.
• Prepare and execute Memorandums of Agreement, Understanding, and Exception, as well as supplemental agreements.
• Monitor labor relations trends, statutory changes, and legal decisions to inform negotiation strategy.

Business Partnership & Operational Integration

• Act as a trusted advisor and representative of management in highly visible labor matters across aviation, marine operations, public safety, and other business lines.
• Maintain a strong understanding of operations and represented work groups through direct engagement, ensuring labor leadership is grounded in how work is performed.

Contract Administration, Grievances & Dispute Resolution

• Oversee the interpretation and administration of collective bargaining agreements, work rules, and related policies.
• Lead and represent the organization in grievance management, mediations, arbitrations, and Employment Relations Board proceedings, in coordination with legal counsel.

Financial Awareness & Sustainability

• Lead cross-functional collaboration with HR, Payroll, Benefits, Legal, and Finance to evaluate the financial implications and enterprise-wide impacts of labor agreements across bargaining units.
• Advance labor strategies that balance wage and benefit structures, cost sustainability, and long-term workforce affordability within a public-sector environment.

Knowledge Management & Capability Building

• Strengthen documentation and knowledge management related to labor practices, side agreements, and contract interpretation to reduce risk and preserve institutional knowledge.
• Promote clarity and consistency in the application of labor provisions across departments.
• Design and deliver training for managers on labor relations fundamentals, contract application, and effective labor management practices.
• Provide leadership, coaching, and performance management for direct report, ensuring high professional standards and continuity in labor relations practices.

Requirements

• 8+ years of progressively responsible experience in labor relations, including leading or owning complex collective bargaining negotiations and advising senior leaders.
• Experience in a public-sector or highly unionized, complex organization with multiple bargaining units and varied contract provisions.
• Strong working knowledge of labor law, collective bargaining, grievance and arbitration processes, and applicable federal and state regulations, including Oregon PECBA or comparable frameworks.
• Working understanding of the financial implications of labor agreements and experience partnering with Payroll, Benefits, Finance, and Legal.
• Proven ability to influence, build trust, and remain calm and effective in high-stakes, high-visibility situations.
• Experience improving documentation, consistency, or knowledge management related to labor practices or contract interpretation.
• Bachelor’s degree in Labor Relations, Human Resources, Business, Social Sciences, or a related field; Master’s degree and/or CLRP, PHR, or SPHR preferred.

Benefits

Medical, dental, vision, basic Life and AD&D, FSA/HRA, STD, LTD, PTO, PERS