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Senior Director / Vice President, Deputy General Counsel

United States, Chicago 177000.00 - 298000.00 USD / Year · Job Posted March 20, 2026
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Job Description

The Senior Director / Vice President, Deputy General Counsel is a senior legal advisor responsible for managing Y-USA’s litigation portfolio, providing enterprise legal guidance, negotiating complex contracts, and overseeing the effective engagement of outside counsel. This role exists to protect Y-USA from legal, financial, fiduciary, and reputational risk by applying experienced legal judgment early, consistently, and at scale across a complex nonprofit and federated environment.

Job Responsibility

  • Manage Y-USA’s litigation docket, including employment, tort, contract, and other civil matters
  • Serve as the primary internal lead on litigation strategy, posture, motion practice, discovery coordination, and resolution
  • Apply disciplined judgment regarding jurisdictional challenges, early dismissal strategies, settlement posture, and escalation thresholds
  • Coordinate insurance alignment, notice obligations, and claims strategy in partnership with Finance and Risk
  • Prepare concise, executive-ready briefings on litigation exposure, trends, and outcomes
  • Conduct portfolio-level analysis of litigation trends to identify systemic risk drivers
  • Serve as a front-line legal risk assessor, providing early triage of emerging disputes, workforce issues, and operational risks
  • Provide legal guidance to executive leadership and business teams on operational, employment, governance, and risk-related matters
  • Advise on sensitive personnel issues, internal disputes, and escalated workplace matters
  • Stay abreast of nonprofit legal developments affecting governance, tax-exempt status, employment, fiduciary duties, and regulatory exposure
  • Lead negotiation of complex, high-risk contracts
  • Provide legal oversight and risk analysis related to emerging technologies
  • Select, manage, and oversee outside counsel across litigation and specialized legal matters
  • Support the CLO in preparing executive leadership and the Board for high-impact legal issues
  • Partner closely with the CLO, CCPO, HR, Finance, IT, and operational leaders
  • Mentor legal staff and contribute to the development of internal legal capabilities

Requirements

  • Juris Doctor or equivalent legal training
  • Active license to practice law in at least one U.S. jurisdiction
  • Minimum of 12 years of experience required
  • Strong background in employment law, contracts, and nonprofit or regulated environments
  • Demonstrated ability to exercise independent judgment on high-risk, sensitive matters
  • Executive presence and comfort advising senior leadership

What we offer

  • medical
  • dental
  • vision
  • defined benefit plan (retirement savings)
  • defined contribution plan (403(b) plan
  • life and disability insurances
  • technology stipend
  • generous paid time off

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