VP, General Counsel

This role is hands-on and leads the Company’s legal strategy, oversees regulatory compliance, and helps the business move decisively while maintaining appropriate legal and regulatory risk controls.  This position is located at JACK Entertainment’s home office in downtown Cleveland, Ohio. 

Essential Functions: 

Executive Leadership & Legal Strategy

• Serve as principal legal advisor to the Board of Managers and executive leadership team.


• Translate complex legal and regulatory issues into clear, practical business guidance.


• Set the Legal team’s priorities, establish scalable processes and infrastructure, and act as a commercially minded business partner in a fast-moving, highly regulated industry.

Regulatory Compliance & Gaming

• Oversee the Company’s regulatory compliance framework, including gaming, alcohol, employment, health and safety, privacy, and anti-money laundering.


• Monitor regulatory developments, advise leadership on compliance posture and risk exposure, and coordinate licensing, renewals, investigations, reporting and other regulatory filings.


• Collaborate with the Director of Compliance and operational teams to build compliant processes and maintain strong relationships with regulators and licensing authorities.

Litigation & Dispute Resolution

• Manage the Company’s litigation portfolio, including employment, premises liability, personal injury, commercial, regulatory and other disputes.


• Develop litigation strategy, make sound and timely decisions regarding risk tolerance and settlement, and direct outside counsel from claim inception through resolution.


• Manage discovery, litigation holds, reporting, reserves, budgets and legal spend.

Commercial Transactions

• Draft and advise on a broad range of commercial agreements, including procurement, technology, marketing, construction, consulting, confidentiality, partnership, licensing and service agreements.


• Develop and maintain contract templates, playbooks and self-service resources that improve consistency, efficiency and the Company’s ability to move quickly.


• Provide transactional counsel and support on acquisitions, strategic initiatives and other business opportunities.


• Draft and negotiate commercial real estate leases, licenses and related documents. 

Labor & Employment

• Advise on the full spectrum of labor and employment matters, including hiring, performance management, separations, wage and hour, leave, accommodations, employee / labor relations and workplace investigations.


• Partner with HR and business leaders to develop and implement practical employment policies, training and risk-mitigation strategies. 

Corporate Governance & Entity Management

• Manage entity formation, annual filings, corporate records and governance documentation, including Board materials, resolutions, minutes and other corporate records.


• Advise the Board and executive leadership on corporate governance, conflicts of interest, delegations of authority and other corporate matters.


• Oversee the Company’s intellectual property portfolio, including trademarks, patents, software licensing and proprietary content in coordination with outside counsel and business stakeholders.

Legal Operations

• Improve legal processes, workflows and service delivery; leverage technology, including AI where appropriate, while maintaining appropriate governance, confidentiality and professional judgment.

Knowledge, Skills & Abilities: 

• Decisive and action-oriented.


• Comfortable operating without extensive support infrastructure and willing to roll up their sleeves to do the work.


• Strong communicator who translates legal complexity into plain business language for executives, Board members and business partners.


• High ownership mentality, sound judgment and the ability to provide practical, solutions-oriented advice that balances business objectives with legal and regulatory risk.


• Executive presence and credibility, with the ability to build trusted relationships and serve as a collaborative, approachable partner the business wants to call.


• Thrives in a fast-paced, entrepreneurial environment where priorities shift and speed matters.


• Highest standards of professionalism, integrity, confidentiality and sound ethical judgment.


• Commitment to continuous improvement and thoughtful use of technology to improve legal and compliance operations.


• Must be proficient in Microsoft Office including Outlook, Word, and Excel, and possess the ability to quickly learn other software


• Ability to read, write and verbally communicate effectively in 

Education and Experience 

• Juris Doctor (J.D.) from an accredited law school.


• Minimum of 10 years of progressive experience as a practicing lawyer, preferably with a combination of law firm and in-house experience.


• Proven track record in commercial contracting, litigation management and advising executive leadership.


• Meaningful experience with labor and employment (including collective bargaining), regulatory compliance, corporate governance, and gaming industry is preferred but not required.


• Experience using or implementing AI and other legal technology tools is a plus. 

Required Certification/License 

• Active license to practice law in at least one U.S. state. Ohio bar admission preferred; candidates eligible for Ohio in-house counsel registration will also be considered.


• Gaming License: Ability to obtain and maintain a key license is required.