Chief Technology & AI Officer

About the Opportunity:

A rapidly growing digital marketing and coaching business for attorneys nationwide is seeking a Chief Technology & AI Officer. This pivotal role focuses on leading technology and AI strategy to support scalable growth and enhance client outcomes across the organization.

Responsibilities:

• Own company-wide technology and AI strategy.
• Define and maintain long-term architecture for the organization and affiliated entities.
• Ensure technology decisions support scalability, leverage, and client results.
• Design and implement an agentic operating model.
• Architect AI agents across sales, service delivery, finance, operations, and internal reporting.
• Define which decisions are automated versus human-led.
• Establish a single source of truth for client and operational data.
• Ensure real-time updates, notifications, and intelligent recommendations across teams.
• Manage governance, security, and compliance, including data security and AI governance standards.
• Ensure compliance across all tools, vendors, and integrations.
• Set standards for tools and platforms, approve or reject technology investments, and manage the technology budget.
• Lead through influence and clarity, avoiding micromanagement.
• Collaborate closely with department leaders to redesign workflows and operating models.

Requirements:

• 5 to 10+ years in senior technology, platform, or systems architecture roles.
• Experience designing and scaling complex, integrated systems.
• Strong understanding of AI, automation, and agent-based architectures.
• Proven strategic decision-maker beyond implementation.
• Experience supporting or integrating multiple business units or acquisitions.
• Exceptional communication skills to translate technical vision into business impact.

Benefits & Perks:

• Medical, dental, and vision insurance with 75% coverage for employees and their families.
• Flexible vacation time to encourage recharging.
• Education budget for courses, events, and books.
• Company activities, outings, and retreats.
• 401(k) plan with a 3% match.
• Flexible work style allowing remote work or office presence.

Key skills/competency:

• AI Strategy
• Technology Leadership
• System Architecture
• Automation
• Data Governance
• Scalability
• Compliance Management
• Strategic Decision-Making
• Workflow Redesign
• Cross-functional Collaboration