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Fractional CTO

Job in Pittsburgh, Allegheny County, Pennsylvania, 15289, USA
Listing for: SMB Team
Full Time position
Listed on 2026-07-13
Job specializations:
  • IT/Tech
    IT Business Analyst
Salary/Wage Range or Industry Benchmark: 150000 - 160000 USD Yearly USD 150000.00 160000.00 YEAR
Job Description & How to Apply Below
Position: Fractional CTO (Full Time Role)

SMB Team is seeking a full‑time internal Fractional CTO to serve our portfolio of law‑firm owner clients. The role involves delivering AI readiness assessments and ongoing fractional CTO services to small law firms, helping them adopt AI tools, strengthen their technology infrastructure, and build internal capability.

The salary for this role is $150,000–$160,000 annually based on experience.

Key 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 (two 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.
Qualifications:
  • 5+ years in a technology leadership role (CTO, VP Engineering, Director of IT, or equivalent) with client‑facing or consulting experience strongly preferred.
  • 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 who can explain AI concepts to non‑technical law firm leadership without condescension.
  • Familiarity with the legal technology landscape (Clio, Net Documents, Harvey, Casetext, etc.) is preferred; deep legal knowledge not required.
  • Experience writing structured deliverables.
  • Must be able to independently execute all Phase 1 deliverables without hand‑holding.
  • Professional presence and clear communication are mandatory for client interactions.
  • No legal background required, but genuine curiosity about the legal industry is essential.
  • 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.
  • Must be available for client‑facing work during standard business hours; occasional travel to client sites may be required.
Benefits:
  • Opportunities to work with top law firms as part of the leading legal marketing and coaching company in the U.S.
  • Medical, dental, and vision insurance coverage for you and your family (75% paid by SMB Team).
  • Flexible vacation time to recharge and maintain work‑life balance.
  • Team member education and learning budget for courses, events, and books.
  • Company activities, outings, and retreats to build culture.
  • 401(k) plan with a 3% match.
  • Work style: work‑from‑home or office – flexible arrangement.

SMB Team is an Equal Opportunity Employer. The policy of SMB Team extends opportunities to all qualified applicants and employees on an equal basis regardless of race, color, gender, age, national origin, religion, citizenship status, marital status, sexual orientation, gender identity, transgender status, physical or mental disability, veteran status, genetic information, pregnancy, or other protected categories.

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