Fractional CTO

This is a fully remote position, open to applicants in Pennsylvania.

📋 Description

• Perform Phase 1 AI Readiness Assessments for small law firms, including technology audits, data infrastructure evaluation, compliance reviews, readiness scoring, opportunity analysis, tool demonstrations, workflow implementation, and delivering final reports.

• Facilitate AI coaching sessions (two per Phase 1 engagement) and act as an on-call AI consultant for clients on Phase 2 retainers.

• Nurture ongoing relationships with Phase 2 clients through monthly check-ins, dashboard upkeep, oversight of AI tool adoption, and light IT/security responsibilities.

• Oversee the client pipeline in collaboration with the SMB Team sales; participate in pre-sales scoping discussions and proposal assistance.

• Keep abreast of the latest legal AI tools (such as Harvey, Clio Duo, Copilot for M365, Casetext, etc.) and revise the SMB Team’s recommended technology stack as necessary.

• Record all client-related activities in the SMB Team's systems; contribute to the practice library with reusable templates and playbooks.

• Promptly report any obstacles, scope alterations, or delivery risks to the CTO.

⛳️ Requirements

• Over 5 years of experience in a technology leadership position (CTO, VP of Engineering, Director of IT, or equivalent); prior experience in a client-facing or consulting role is highly desirable.

• Proven hands-on experience with AI tools and workflows, particularly in professional services contexts (legal, finance, or healthcare experience is a plus).

• Capability to independently conduct a credible technology and data infrastructure audit; familiarity with cloud platforms (M365/Google Workspace), practice management software, and integration tools is essential.

• Strong and confident communicator, able to convey AI concepts to non-technical law firm leadership without being patronizing.

• Preferred familiarity with the legal technology landscape (Clio, NetDocuments, Harvey, Casetext, etc.); extensive legal knowledge is not mandatory.

• Experience in creating structured deliverables is required.

• Ability to independently manage all Phase 1 deliverables without supervision—this role encompasses the entire engagement from kickoff to report submission.

• Must be comfortable representing the SMB Team with law firm clients; a professional demeanor and clear communication are essential.

• A legal background is not necessary, but a genuine curiosity about the legal field and a willingness to quickly understand the industry is crucial.

• Must stay updated on generative AI tools and be capable of demonstrating them effectively to non-technical audiences.

• Willingness to work within the SMB Team’s systems and contribute to collaborative playbooks is essential (this is not a solo role).

• Availability for client-facing activities during standard business hours; occasional travel to client locations may be required.

🏝️ Benefits

• We cover 75% of your Medical, Dental, and Vision insurance for YOU and YOUR FAMILY.

• FLEXIBLE VACATION TIME - We encourage you to take time off to recharge so you can perform your best at work.

• Budget for team member education and learning on courses, events, and books.

• Company-sponsored activities, outings, and retreats.

• 401(k) plan with a 3% match.

• You can choose to work from home or come to the office. The choice is yours!