Managing Director, Legal & Associate General Counsel

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.

Behind our success is the unshakeable belief in the value of our people. We value diversity, inclusivity and a sense of belonging. We celebrate work and life events, and we partner with our clients and communities to make great things happen.

We’ve earned recognition time and again as a top place to work—named among the best by respected organizations like Glassdoor and U.S. News & World Report. We’re also proud to be recognized for one of the country’s Top 50 Midsize Early Talent Programs through RippleMatch’s Campus Forward Awards. There’s never been a better time to be part of Insperity, and our best work is still ahead. Learn more at Insperity.com.

Why Insperity?

Flexibility: Over 80% of Insperity’s jobs have flexibility. We want your time to have balance, whether it’s spent with coworkers, clients, family or your community.

Career Growth: Insperity provides many ways to grow with the company. We offer continuous learning programs, mentorship opportunities and ongoing training.

Well-Being: Our total rewards package includes generous paid time off, top-tier medical, dental and vision benefits, health & wellness support, paid volunteer hours and much more. We take care of our people so that you can do your best work.

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 primarily provides practical, business‑oriented legal counsel on privacy compliance, AI governance, and technology contracting, including SaaS and other data‑driven commercial arrangements, both with clients and vendors. This position also requires a significant level of cross-functional collaboration regarding matters having Company-wide impact and requires a team-oriented approach, with the flexibility and willingness to support legal matters beyond the candidate’s core specialty.

RESPONSIBILITIES

• Serves as a key internal legal advisor on data privacy, cybersecurity, data governance, and technology matters, and helps monitor and interpret privacy, cybersecurity, and AI‑related regulatory developments applicable to the Company and translate those developments into actionable guidance, policies, and contractual provisions, in collaboration with the Data Privacy Group of the Company’s information technology organization and, where appropriate, outside counsel.
• Reviews, drafts, and negotiates a broad range of commercial and technology agreements, including MSAs, SaaS and data processing agreements, software licenses and subscriptions, and NDAs, including agreements with AI, data, security, and IP components.
• Provides guidance on strategic transactions and the development of new solutions and related contractual terms, including helping to identify and assess privacy, data, security and AI-related risks, and partnering with business teams to design workable, risk-appropriate solutions.
• Assists with providing advice on the lawful and responsible use of AI and machine learning tools, including reviewing use cases and advising on governance, transparency, testing and monitoring, notices, risk assessments, and human‑in‑the‑loop controls.
• Advises on and support legal aspects of cybersecurity incidents, including investigation support, response coordination, and assessment of notification obligations, in partnership with the incident response team.
• Supports the sales organization in connection with client and prospect engagements by responding to inquiries submitted to the Legal Department (including those relating to privacy) and participating in negotiations as needed.
• Contributes to and helps maintain contract templates, playbooks, and internal knowledge bases; partners with internal SMEs and outside counsel as appropriate.
• Assists with reviews of marketing materials, intellectual property‑related issues, and other general corporate and commercial matters as needed, including coordination with internal teams and outside counsel.
• Collaborates 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.
• Assists the General Counsel, Group General Counsel, and other in-house counsel in providing strategic legal guidance to management and other internal stakeholders that aligns with business objectives while mitigating risk.
• Develops and maintains strong professional working relationships with internal clients and external law firms.
• Performs other duties as may be assigned by the Group General Counsel.

SUPERVISORY RESPONSIBILITY

Supervises others: No direct reports; indirectly directs and oversees Assistant General Counsel, contract counsel, and Legal Administrative Assistants in the Transactions & Corporate Law Practice Group and 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).
• Strong problem solver who can work independently or in a team to develop solutions to accomplish business objectives in a complex, regulated industry.
• Solid understanding of data privacy, cybersecurity, and technology contracting issues, with the willingness to deepen such understanding over time and 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, as well as the 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, with strong fluency in leveraging technology to support efficient legal operations.
• Demonstrates initiative in adopting and optimizing legal technology, including AI and automation tools, and proactively identifies and utilizes opportunities to leverage these technologies to streamline workflows and improve the efficiency, consistency, and scalability of the Legal Department function.
• Demonstrates 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 also desired but not required.
• Travels: Yes, up to 5% of time​

At Insperity, we celebrate the diversity of our employees and our leadership. Insperity is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status or any other characteristic protected by law.