Fractional CTO (Full Time Role)

SMB Team • Philadelphia, PA

37d • $150,000 - $160,000 • Hybrid

About The Position

SMB Team is seeking an internal, full-time hire to serve as part of their team of Fractional CTOs for their portfolio of law firm owner clients. This role involves delivering AI readiness assessments and ongoing fractional CTO services to small law firms. The goal is to help these firms adopt AI tools, strengthen their technology infrastructure, and build internal capability, ultimately generating revenue and client impact for SMB Team.

Requirements

• 5+ years in a technology leadership role (CTO, VP Engineering, Director of IT, or equivalent)
• Experience in a client-facing or consulting capacity strongly preferred
• Demonstrated hands-on experience with AI tools and workflows, including generative AI applications in professional services contexts (legal, finance, or healthcare a plus)
• Ability to conduct a credible technology and data infrastructure audit independently; comfortable with cloud platforms (M365/Google Workspace), practice management software, and integration tooling
• Clear, confident communicator. Able to explain AI concepts to non-technical law firm leadership without condescension
• Experience writing structured deliverables
• Must be able to independently execute all Phase 1 deliverables without hand-holding—this role owns the full engagement from kickoff to report delivery
• Must be comfortable as the face of SMB Team with law firm clients; professional presence and clear communication are non-negotiable
• Must have genuine intellectual curiosity about the legal industry and willingness to learn the landscape quickly
• Must be current on generative AI tools and able to demonstrate them credibly to non-technical audiences
• Must be willing to work within SMB Team’s systems and contribute to shared playbooks (i.e. this is not a solo practice)
• Must be available for client-facing work during standard business hours; travel to client sites may occasionally be required

Nice To Haves

• Familiarity with legal technology landscape preferred (Clio, NetDocuments, Harvey, Casetext, etc.); deep legal knowledge not required

Responsibilities

• Conduct Phase 1 AI Readiness Assessments for small law firms (technology audit, data infrastructure mapping, compliance review, readiness scoring, opportunity analysis, tool demos, workflow implementation, and final report delivery)
• Deliver AI coaching sessions (2 per Phase 1 engagement) and serve as on-call AI advisor for Phase 2 retainer clients
• Maintain ongoing Phase 2 retainer relationships: monthly check-ins, dashboard maintenance, AI tool adoption oversight, and light IT/security tasks
• Manage client pipeline in coordination with SMB Team sales; contribute to pre-sales scoping calls and proposal support
• Stay current on legal AI tooling (Harvey, Clio Duo, Copilot for M365, Casetext, etc.) and update SMB Team’s recommended stack as the landscape evolves
• Document all client-facing work in SMB Team’s systems; contribute reusable templates and playbooks to the practice library
• Flag blockers, scope changes, or delivery risks to the CTO in a timely manner

Benefits

• We pay for 75% of your Medical, Dental, Vision insurance for YOU and YOUR FAMILY.
• FLEXIBLE VACATION TIME
• Team member education and learning budget on courses, events and books.
• Company activities, outings, and retreats.
• 401(k) with a 3% Match.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed