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?

Final question: When faced with a challenge, do you get excited or run away?

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Disability Law Group is dedicated to guiding individuals and families through some of life’s most challenging moments. From Social Security Disability benefits to Veterans’ claims, we advocate for people who need strong, compassionate representation. Our team is based in Troy, Michigan, and we’re known for combining deep legal expertise with a client-first culture that values empathy, precision, and results.

We’ve grown steadily by staying committed to both our mission and our people. At Disability Law Group, success is measured not only in cases won but in lives changed. This is where advocacy meets accountability, and where every member of our team plays a role in creating impact.

This role is ideal for a strategic, hands-on technology leader who can help the firm use AI, automation, CRM/case management tools, analytics, and legal technology responsibly and effectively. The Director of AI and Legal Technology will own AI strategy, CRM evaluation, workflow automation, analytics, governance, and change management.

This person will support the 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. This is not a traditional IT support role; it is a legal technology transformation role focused on reducing friction, improving consistency, increasing visibility, and helping the firm serve clients more effectively while protecting confidentiality, accuracy, ethics, and client trust.

What you’ll do:

• 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.

What we’re looking for:

• 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.

Nice to have:

• 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.

Why you should work here:

• 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.