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SkillMastery
Careers

Build the Infrastructure
for AI Transformation

We are not a training company. We build the operating system for enterprise AI transformation. If you are an operator who drives outcomes, not decks — we want to hear from you.

Our Mission

Transformation, not education

To equip organizations with the infrastructure, systems, and leadership capacity to thrive in the age of AI. Every engagement we run is structured around execution, accountability, and measurable outcomes — not course catalogs and completion rates.

Who We Hire

Operators. Builders. Leaders.

  • Operators who drive execution and accountability over theory

  • Builders who create systems and infrastructure, not just content

  • Leaders who thrive in ambiguity and make decisions under pressure

  • People who measure their impact in outcomes, not activity

Open Roles

Fractional Chief AI Officer (fCAIO)

Lead enterprise AI transformation engagements as an embedded executive partner

Actively Hiring
Contract / Part-time Remote (US preferred) Flexible — 10–20 hrs/week per client

About the Role

As a Fractional Chief AI Officer at SkillMastery, you serve as an embedded executive partner inside client organizations. You are not an advisor who sends emails and slides. You run the operating cadence, facilitate leadership alignment, coordinate the people driving execution, and deliver the Monthly Business Review.

This role is for operators who have led transformation — who know what it feels like to own an outcome inside an organization, navigate executive dynamics, and make a complex program actually run.

Responsibilities

  • Serve as embedded fractional Chief AI Officer for client organizations

  • Design and run the monthly AI transformation operating cadence

  • Facilitate executive alignment sessions and 90-day roadmap development

  • Coordinate AI Champions and Internal Operators across client departments

  • Deliver Monthly Business Reviews with transformation scorecards

  • Identify and escalate blockers that slow client transformation progress

  • Build client capability over time — not dependency on you

Qualifications

  • Proven experience in executive leadership, transformation, or operations roles

  • Deep familiarity with enterprise AI tools, workflows, and adoption dynamics

  • Track record of managing multi-stakeholder programs with measurable outcomes

  • Ability to navigate C-suite relationships and present with clarity and confidence

  • Strong systems thinking — comfortable designing and running operating cadences

  • Comfortable with ambiguity and skilled at creating structure where none exists

Apply for This Role

Don't see the right fit?

We are always interested in operators, builders, and leaders who want to drive AI transformation at scale. Submit a general interest application and tell us what you do best.

Submit General Interest

Build the future of AI transformation

Work with organizations that are serious about execution. Drive outcomes that compound.

Apply Now