Fractional CTO (Full Time Role)

About the Role

The role entails conducting AI readiness assessments, delivering AI coaching sessions, and serving as an on-call AI advisor for law firms. You will also be responsible for maintaining ongoing relationships with clients, managing the client pipeline, and contributing to pre-sales scoping calls and proposal support.

SMB Team is a fast-growing company that is committed to providing its employees with a flexible and supportive work environment. As a remote worker, you will have the opportunity to work from home or come into the office, depending on your preferences.

What You Will Do

• Conduct Phase 1 AI readiness assessments for small law firms, including technology audits, data infrastructure mapping, compliance reviews, readiness scoring, opportunity analysis, tool demos, workflow implementation, and final report delivery
• Deliver AI coaching sessions and serve as an on-call AI advisor for Phase 2 retainer clients
• Maintain ongoing Phase 2 retainer relationships, including monthly check-ins, dashboard maintenance, AI tool adoption oversight, and light IT/security tasks
• Manage the client pipeline in coordination with SMB Team's sales team
• Contribute to pre-sales scoping calls and proposal support
• Stay current on legal AI tooling and update SMB Team's recommended stack as the landscape evolves
• Document all client-facing work in SMB Team's systems and contribute reusable templates and playbooks to the practice library
• Flag blockers, scope changes, or delivery risks to the CTO in a timely manner

What We Are Looking For

• 5+ years of experience in a technology leadership role, such as CTO, VP Engineering, Director of IT, or equivalent
• Experience in a client-facing or consulting capacity, with a strong ability to communicate technical concepts to non-technical stakeholders
• Demonstrated hands-on experience with AI tools and workflows, including generative AI applications in professional services contexts
• Ability to conduct a credible technology and data infrastructure audit independently
• Comfort with cloud platforms, practice management software, and integration tooling
• Clear and confident communication skills, with the ability to explain AI concepts to non-technical law firm leadership
• Familiarity with the legal technology landscape, including Clio, NetDocuments, Harvey, and Casetext
• Experience writing structured deliverables and executing all Phase 1 deliverables without hand-holding

Nice to Have

• Experience working in the legal industry or with law firms
• Familiarity with legal AI tools, such as Harvey, Clio Duo, and Copilot for M365
• Experience with project management software and tools
• Certification in AI or a related field

Benefits and Perks

• Flexible vacation time and remote work options
• 75% of medical, dental, and vision insurance paid for you and your family
• Education and learning budget for courses, events, and books
• Company activities, outings, and retreats
• 401(k) with a 3% match
• Opportunities for professional growth and development
• Access to the latest AI tools and technologies
• Collaborative and supportive work environment

• Be prepared to demonstrate your expertise in AI tools and workflows, and your ability to communicate complex concepts to non-technical stakeholders.
• Highlight your experience working with law firms or in the legal industry, and your familiarity with legal AI tools and workflows.
• Emphasize your ability to work independently and manage multiple clients and projects simultaneously.
• Be prepared to discuss your experience with cloud platforms, practice management software, and integration tooling.
• Show a willingness to learn and adapt to new technologies and workflows, and a commitment to staying current on the latest developments in the field.
• Make sure to tailor your resume and cover letter to the specific requirements and qualifications listed in the job description.
• Be prepared to ask informed questions during the interview process, such as what the typical client engagement looks like, and what the biggest challenges are in the role.