AI Enablement Facilitator
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Job Description
AI Enablement Facilitator helping Scale Army, an international staffing agency, sell and deliver AI implementation pods to U.S.-based companies. Facilitating executive workshops, live AI builds, and roadmap closes.
Responsibilities:
- Present free AI diagnoses to CEOs or COOs as findings and convert credibility into paid Leadership Intensives
- Run the close with the account executive, owning the narrative and the ask
- Facilitate deep-dive sessions inside client systems and data to identify ranked AI opportunities
- Lead hands-on build sessions where executives create clickable first versions using their own data and AI tools
- Teach AI concepts, build-versus-buy-versus-hire considerations, and routine-versus-judgment distinctions
- Manage deliverables between sessions, including data exports and input from client leaders
- Deliver approximately 70% fixed, reusable Intensive content and 30% client-specific content
- Co-present 90-day technical roadmaps with senior engineers and close pod engagements
- Position client-managed pods, fully managed pods, on-call senior support, and credited Intensive fees correctly
- Handle objections regarding in-house hiring, nearshore talent, and implementation risk
- Provide weekly structured feedback to diagnosis systems, decks, playbooks, and close scripts
- Record sessions with consent, tag important moments, and support facilitator onboarding
- Help define hiring standards and train future facilitators
- Deliver two to three Intensive sessions, one or two diagnosis presentations, and one roadmap close in a typical week
- Run the full client-facing arc and meet conversion, session-quality, deal-durability, and machine-contribution targets
Requirements:
- 5+ years in quota-carrying consultative B2B sales, sales engineering, or paid advisory selling to founders, CEOs, and C-level operators
- Specific executive-level closes with numbers attached and references who were in the room
- Experience running paid workshops, executive offsites, enablement programs, or high-stakes demos
- Working AI fluency; daily use of AI tools and ability to live-demo a working automation or agent flow
- Ability to explain technical approaches in plain English and provide credible build-vs-buy recommendations
- Business-process literacy, including ability to map manual hours in processes such as quote-to-cash or month-end close
- Magnetic, quick, slightly irreverent presence combined with disciplined agenda and closing skills
- Full professional fluency in spoken and written English
- Spanish or Portuguese is a plus, not a requirement
- Availability to work 9 AM–5 PM EST / U.S. business hours aligned with client time zones
- Resume must be submitted in English and PDF format
- Must complete the application form and record a video showcasing skills
Benefits:
- Full-time role at 40 hours/week
- Remote work arrangement
- Opportunity to work with international talent and U.S.-based clients
- Career progression toward facilitation-team leadership or revenue leadership
- Training and mentorship through founder shadowing and co-facilitation during the first 90 days
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