Chief Technology Officer (CTO) AI, Legal Technology & Systems Integration

• Lead the firm’s AI, legal technology, automation, systems integration, and infrastructure strategy.
• Work directly with attorneys and leadership to evaluate existing workflows, identify inefficiencies, and develop technology-driven solutions.
• Design, develop, implement, and scale AI-powered tools, workflow automation, and legal technology integrations.
• Optimize litigation workflows, case management systems, document management, and legal operations.
• Integrate AI solutions with existing legal technology platforms to improve efficiency, accuracy, and scalability.
• Evaluate and enhance existing systems, including case management platforms, legal research tools, and internal applications.
• Oversee cybersecurity, data privacy, AI governance, and compliance frameworks.
• Lead developers, IT teams, consultants, and technology vendors while remaining actively involved in technical development and implementation.
• Manage technology budgets, project execution, and strategic investments.

Direct Counsel is seeking an experienced, hands-on Chief Technology Officer (CTO) to lead AI innovation, legal technology development, automation, and systems integration for a rapidly growing plaintiff-side employment law firm.

The ideal candidate brings a strong combination of direct law firm experience, technical leadership, AI implementation, and hands-on experience developing and integrating legal technology solutions.

We are specifically seeking someone who understands law firm operations, litigation workflows, case management systems, and attorney technology needs, and can translate those needs into practical, scalable solutions.

This position requires more than overseeing technology projects. The successful candidate must have experience working directly with attorneys to identify workflow challenges, develop solutions, and implement technology that improves legal operations., * 10+ years of technology leadership experience, including CTO, CIO, VP of Technology, Head of Engineering, or similar roles.

• Direct experience working within a law firm, with a strong understanding of law firm operations and attorney workflows.
• Demonstrated hands-on experience developing, implementing, and integrating legal technology solutions, rather than solely overseeing projects.
• Experience with litigation workflows, legal case management systems, and legal process automation.
• Proven experience implementing AI solutions, automation tools, and systems integrations within legal environments.
• Experience working directly with attorneys to understand operational needs and translate them into functional technology solutions.
• Strong knowledge of software development, cloud infrastructure, cybersecurity, data management, and technology risk.
• Proven ability to lead technical teams while remaining involved in solution architecture and execution.

Preferred Qualifications

• Hands-on experience with legal technology platforms such as Filevine, Clio, Litify, Actionstep, Trellis, LexisNexis, or comparable systems.
• Experience developing or integrating AI-powered litigation tools, case management automation, document analysis, and attorney workflow solutions.
• Background supporting plaintiff-side litigation, employment law, or high-volume litigation practices.
• Experience integrating third-party legal platforms, APIs, and AI applications.
• J.D. and prior legal practice experience are highly desirable but not required.
• Experience building scalable technology infrastructure for a growing law firm.

Join a rapidly growing, forward-thinking law firm that has already invested significantly in AI and automation and is looking for a technology leader to take its capabilities to the next level.

This is an opportunity to work directly with executive leadership and attorneys to build, implement, and scale practical AI and legal technology solutions that transform how the firm operates.

This is a strategic, hands-on technology leadership position-not a traditional IT management or project oversight role.

Direct Counsel is committed to connecting exceptional talent with premier legal employers and fostering inclusive hiring practices.