Director, Employment & Litigation Counsel

Five9 is seeking a highly strategic Director, Employment and Litigation Counsel to partner with the People team as lead advisor on global employment and risk-related matters, as well as manage Five9's litigation and disputes and identify, assess and mitigate potential risks.

Reporting directly to Five9's SVP, Legal, this role combines corporate strategy, corporate development, PMO leadership, and Chief of Staff responsibilities. The ideal candidate will be responsible for providing expert legal advice and representation in various global employment matters, with a focus on protecting the Five9, the rights of employees and ensuring compliance with applicable employment laws, as well as advising on employee relations matters.

This position offers an opportunity to work on complex cases, including whistleblower claims, class actions, and investigations. Additionally, the Senior Director will identify, assess and mitigate potential legal risks to Five9 to drive risk-adjusted business outcomes while protecting Five9 by providing subject matter expertise on litigation, arbitration and disputes, from initial communications through final resolution.

This role will collaborate directly with key stakeholders (Compliance, People, IT, Security, Finance, etc.) to devise and implement creative solutions to risk-related matters.

Key Responsibilities

• Employment • Advise on global employment laws and regulations, and partner closely with the People team on employment matters throughout the employee lifecycle, including hiring and terminations, talent acquisition, employee relations, compliance trainings, policy and handbook management, accommodations and benefits. • Represent the company in negotiations, mediations, and court proceedings. • Manage a diverse caseload involving employment disputes. • Conduct legal research and prepare legal documents such as briefs, memos, and pleadings. • Stay updated on changes in global employment law and industry trends. • Provide training and consultation to the business on best practices in employment matters.

Litigation Management

• Develop and implement litigation strategies in collaboration with external and internal legal counsel, as well as business stakeholders.
• Manage investigations, enforcement actions, and litigation, arbitration and disputes from commencement through resolution, providing appropriate updates to cross-functional partners and leadership regarding risk, financial impact, and opportunities to resolve.
• Prepare and review legal documents, including pleadings, motions, and settlement agreements.
• Evaluate and mitigate legal risks associated with current and potential litigation, including coordination with risk management/insurance.
• Advise the sales, services and operational teams regarding customer escalations and customer disputes.
• Respond timely to requests for information and subpoenas from regulators and others, and assist the company in developing strong procedures for compliance with these requests.
• Monitor trends and legal developments, particularly those that impact the financial services and technology industries, analyze the implications for the company, and ensure the company is well-positioned to respond and react accordingly.

Risk

• Partner with diverse internal business teams (Compliance, People, IT, Security, Finance, etc.) to proactively identify legal and regulatory risks facing the company and develop and implement strategies for mitigating those risks while successfully enabling the company's business objectives.
• Partner closely with Compliance and other departments to provide pragmatic and actionable advice, develop new policies, or implement strategic revisions to existing policies/procedures as part of the company's risk management.
• Support other risk management initiatives, including training and internal investigations.

Strategic Counsel

• Provide proactive legal advice to senior management on litigation and compliance-related issues.
• Keep abreast of legal developments and industry trends to anticipate potential legal challenges and opportunities.

Requirements

• Juris Doctor (JD) degree from an accredited law school and admitted to practice in at least one jurisdiction.
• 5+ years working experience in law firms and/or in-house, with a preference in-house experience.
• Strong understanding of employment law, including whistleblower-related issues and class actions.
• Deep experience in litigation, arbitration, and/or regulatory enforcement actions, including responsibility for independently managing complex disputes with employees, customers, regulators, third parties, or others from commencement to resolution.
• Experience managing outside counsel.

Skills, Personal Traits and Attributes

• Exceptional strategic thinking with the ability to translate insight into execution.
• Excellent written and verbal communication skills, both internal (memos, guides, presentations) and external (counterparties, regulator communications).
• Ownership mentality and comfort working on complex matters that require analysis and judgment.
• High comfort with ambiguity and complex, fast-moving environments.
• Proven ability to build and scale high-performing teams.
• High EQ, low ego, and strong bias for action.
• Trusted advisor who balances legal risk with commercial practicality.