Director of AI and Legal Technology

Are you the kind of technology leader who can look at a messy workflow, spot the friction, and build practical systems that actually make people’s jobs easier?

Do you know how to use AI, automation, data, and legal technology to improve efficiency without creating shiny chaos?

Can you translate technical possibilities into real operational improvements attorneys, staff, and leadership can actually use?

• Please do not reach out through our website's contact information (telephone, email, or web chat) or via direct messaging on any social media platform.

• →AI Strategy & Practical Implementation: Identify, evaluate, and guide practical AI use cases that improve efficiency, accuracy, and responsible adoption across the firm.
• →Analytics, Adoption & ROI Measurement: Recommend KPIs, dashboards, and reporting tools to measure AI adoption, CRM usage, workflow efficiency, automation impact, team adoption, and ROI. Help leadership understand whether technology investments are producing measurable value.
• →Legal Technology & Workflow Optimization: Support evaluation, selection, migration, and optimization of the firm’s next CRM/case management platform, which may include Salesforce, Filevine, a custom CRM, or another solution. Compare potential systems using clear decision criteria, map current workflows, identify automation opportunities, and ensure technology decisions fit the firm’s real day-to-day needs.

• →Data, Reporting & KPI Visibility: Improve dashboards, data quality, and KPI reporting so leadership has clear visibility into performance and operational bottlenecks. 
• →Automation & Systems Improvement:  Find repetitive tasks, build or coordinate automations, improve integrations, and ensure systems work reliably after rollout.
• →Training & Change Management: Train the team, create practical documentation, and build buy-in so attorneys and staff can confidently adopt new tools and processes. Work collaboratively with the existing IT team members to support adoption, reinforce clear workflows, and ensure technology changes are implemented with clarity, consistency, and team trust.
• →Collaborative IT Leadership: Partner with, guide, and support an existing IT team member involved in AI, CRM/case management, automation, and legal technology initiatives. Clarify roles, responsibilities, priorities, and ownership so projects move forward smoothly without confusion, duplicated effort, or morale issues.
• →Governance, Compliance & Risk Management: Create responsible AI and technology standards that protect confidentiality, accuracy, compliance, security, and client trust. 
• →Client Experience & Service Improvement: Use technology to improve communication, handoffs, escalations, and service consistency so the team can focus more on client advocacy.

• Experience leading AI, legal technology, automation, systems, reporting, or workflow improvement initiatives.
• Strong understanding of law firm operations or other compliance-driven professional services environments.
• Ability to map workflows, identify inefficiencies, and implement practical solutions.
• Strong data and KPI mindset, with experience creating or improving dashboards and reports.
• Experience supporting technology implementation, system migration, or process redesign.
• Strong communication skills with the ability to work across attorneys, staff, leadership, and vendors.
• Collaborative leadership style with the ability to coach, delegate, and work productively with an existing IT team member or direct report while maintaining clarity, accountability
• Ability to train teams, manage change, and drive adoption.
• Sound judgment around confidentiality, data privacy, legal ethics, and responsible AI use.
• Highly organized, proactive, and comfortable owning projects from idea to implementation.

• Experience in a plaintiff-side law firm, disability law firm, veterans’ benefits practice, or high-volume legal services environment.
• Familiarity with Salesforce, Filevine, Prevail, Clio, Litify, SmartAdvocate, custom CRM tools, or similar systems.
• Experience evaluating, selecting, migrating, or optimizing CRM/case management platforms.
• Experience comparing technology options using decision matrices, business requirements, workflow fit, adoption needs, reporting capability, cost, scalability, and risk.
• Experience with workflow automation, APIs, no-code tools, dashboards, legal AI tools, or CRM integrations.
• Experience creating AI policies, technology governance standards, risk controls, or firmwide training materials.
• Experience designing dashboards or KPI frameworks to measure adoption, efficiency, productivity, and ROI.

• Mission-driven work: Help a growing firm serve clients during some of the most challenging moments of their lives.
• High-impact role: Your work will directly improve workflows, reporting, accountability, and client service.
• Room to build: You will have the opportunity to shape the firm’s AI and legal technology roadmap.
• Collaborative culture: Work with a team that values accountability, empathy, precision, and results.
• Practical innovation: Use technology to solve real problems — not just chase shiny tools.

At Disability Law Group, you’ll do more than manage technology. You’ll help build the systems, workflows, and AI strategy that allow the firm to operate with greater clarity, consistency, and impact.

This is your chance to step into a role where innovation, accountability, and client service meet.