Managing Director, Legal & Associate General Counsel

About the Company

Insperity provides the most comprehensive suite of scalable HR solutions available in the marketplace with an optimal blend of premium HR service and technology. With more than 90 locations throughout the U.S., Insperity is currently making a difference for thousands of businesses and communities nationwide. We value diversity, inclusivity, and a sense of belonging, celebrating work and life events while partnering with clients and communities. Insperity has earned recognition as a top place to work by organizations like Glassdoor and U.S. News & World Report, and as a Top 50 Midsize Early Talent Program through RippleMatch’s Campus Forward Awards.

Why Insperity?

• Flexibility: Over 80% of Insperity’s jobs offer flexibility to balance time with coworkers, clients, family, or community.
• Career Growth: Continuous learning programs, mentorship opportunities, and ongoing training.
• Well-Being: Total rewards package includes generous paid time off, top-tier medical, dental, and vision benefits, health & wellness support, paid volunteer hours, and more.

About the Role

This role serves as a senior legal advisor on data privacy, cybersecurity, and technology matters, while supporting complex commercial and technology transactions across the Company. The Associate General Counsel partners closely with business, privacy, IT, and product teams to identify and mitigate data-related risks, enable the responsible use of emerging technologies (including artificial intelligence), and support the development and delivery of new products and services. The position provides practical, business-oriented legal counsel on privacy compliance, AI governance, and technology contracting, including SaaS and other data-driven commercial arrangements with clients and vendors.

Responsibilities

• Serve as a key internal legal advisor on data privacy, cybersecurity, data governance, and technology matters. Monitor and interpret privacy, cybersecurity, and AI-related regulatory developments, translating them into actionable guidance, policies, and contractual provisions in collaboration with the Data Privacy Group and outside counsel.
• Review, draft, and negotiate a broad range of commercial and technology agreements, including MSAs, SaaS and data processing agreements, software licenses and subscriptions, and NDAs, particularly those with AI, data, security, and IP components.
• Provide guidance on strategic transactions and the development of new solutions, including identifying and assessing privacy, data, security, and AI-related risks, and partnering with business teams to design risk-appropriate solutions.
• Advise on the lawful and responsible use of AI and machine learning tools, including reviewing use cases and advising on governance, transparency, testing, monitoring, notices, risk assessments, and human-in-the-loop controls.
• Support legal aspects of cybersecurity incidents, including investigation, response coordination, and assessment of notification obligations in partnership with the incident response team.
• Support the sales organization by responding to legal inquiries (including privacy-related) and participating in negotiations as needed.
• Contribute to and maintain contract templates, playbooks, and internal knowledge bases, partnering with internal subject matter experts and outside counsel.
• Assist with reviews of marketing materials, intellectual property issues, and other general corporate and commercial matters, coordinating with internal teams and outside counsel.
• Collaborate across the Legal Department and with cross-functional teams, proactively supporting colleagues and contributing to matters outside core areas of expertise as business needs evolve.
• Assist the General Counsel, Group General Counsel, and other in-house counsel in providing strategic legal guidance to management and internal stakeholders that aligns with business objectives while mitigating risk.
• Develop and maintain strong professional working relationships with internal clients and external law firms.
• Perform other duties as assigned by the Group General Counsel.

Supervisory Responsibility

No direct reports; indirectly directs and oversees Assistant General Counsel, contract counsel, and Legal Administrative Assistants in the Transactions & Corporate Law Practice Group. Assists in training and educating team members on privacy-related contract provisions and review practices.

Qualifications

• Doctor of Jurisprudence (J.D.) Degree from an accredited law school is required.
• Minimum seven (7) years of transactional legal experience, with a focus on negotiating and drafting agreements and knowledge of contract law, privacy law, and general corporate law.
• Demonstrated experience negotiating and advising on SaaS, data-driven, and technology-enabled commercial agreements.
• Current law license required, preferably from the State of Texas.
• CIPP/US certification preferred (or willingness to obtain, with Company support, within a reasonable period).

Skills

• Strong problem solver who can work independently or in a team to develop solutions in a complex, regulated industry.
• Solid understanding of data privacy, cybersecurity, and technology contracting issues, with the ability to translate legal requirements into practical, business-ready guidance.
• Experience with SaaS and cloud-based solutions, data processing arrangements, and AI-enabled products and services, including associated commercial, contractual, and risk considerations.
• Excellent contract drafting and negotiation skills, with sound judgment and a business-minded approach to risk identification and mitigation.
• Ability to manage complex matters, prioritize effectively, and deliver timely, high-quality work in a fast-paced environment.
• Clear, persuasive communicator with the ability to work effectively with a diverse range of stakeholders, including senior leadership.
• Highly collaborative, adaptable, and able to work independently when needed; demonstrates tact, diplomacy, and discretion when handling sensitive issues.
• Highly proficient with Microsoft 365 and experienced in CLM systems and other legal technology platforms.
• Demonstrates initiative in adopting and optimizing legal technology, including AI and automation tools, to streamline workflows and improve efficiency, consistency, and scalability.
• Sound judgment in identifying when to escalate matters or engage outside counsel, and effectively incorporates such guidance into practical, business-oriented solutions.
• Experience working with large sales and marketing organizations is desired but not required.

Schedule

Travel required: up to 5% of time.