AI Enablement Facilitator – Executive Sales & Implementation

Role Overview

Scale Army is seeking an AI Enablement Facilitator to lead the commercial and delivery middle of our AI Implementation Pods business. You will be the primary client-facing executive who guides mid-market companies from free AI diagnosis through paid Leadership Intensives to signed 90-day pod engagements. This role combines consultative B2B sales, executive facilitation, and AI product delivery into one integrated craft.

Key Responsibilities

• Present free AI diagnoses to C-level executives as credible findings, then convert them into paid 30-day Leadership Intensives with 40%+ conversion target
• Facilitate high-stakes working sessions where executives map manual processes, identify AI opportunities, and build clickable prototypes on their own data
• Co-present 90-day technical roadmaps with senior engineers and close pod engagements with 50%+ conversion from completed Intensives
• Handle complex objections (in-house hiring, nearshore concerns, execution risk) with proof-based responses and fast-start guarantees
• Generate weekly structured feedback on session outcomes, objection patterns, and playbook improvements to continuously sharpen the delivery system
• Shadow and co-facilitate sessions during onboarding; lead independently by day 60; mentor future facilitators as the team scales

What You Bring

• Executive-room selling: 5+ years in quota-carrying consultative B2B sales, sales engineering, or paid advisory to founders and C-suite, with named closes and references
• Facilitation under stakes: Proven experience running paid workshops, executive offsites, or high-stakes demos where session quality directly impacted revenue
• Working AI fluency: Daily hands-on use of AI tools; ability to live-demo automation or agent flows; credible build-vs-buy analysis; no hand-waving on technical concepts
• Business-process literacy: Can map manual hours from operational descriptions; backgrounds in operations consulting, revenue operations, or P&L management are strong signals
• Executive presence: Magnetic, quick, slightly irreverent personality paired with genuine discipline—tight agendas, on-time delivery, consistent closing
• English fluency: Full professional proficiency, spoken and written, for daily US executive presentations

Strong Pluses

• Experience selling or delivering paid diagnostics, assessments, or pilots that converted into recurring engagements
• Direct experience with nearshore delivery teams and ability to address related objections authentically
• Personal AI side projects (automation stacks, agents, internal tools) you can demonstrate
• Background at services firms during staffing-to-solutions transitions or outcome-based consulting

First 90 Days

1. Days 1–30 (Absorb): Shadow founders on all session types; master diagnosis system, Intensive kit, and pricing; co-facilitate one Intensive; pass internal certification by delivering full core to team
2. Days 31–60 (Invert): Lead at least two Intensives end-to-end; present three+ diagnoses; close your first diagnosis-to-Intensive deal solo
3. Days 61–90 (Own): Run full client arc independently; close first pod without founder present; ship first playbook revisions

Success Metrics

• Diagnosis-to-Intensive conversion: ≥40%
• Intensive-to-Pod conversion: ≥50%
• Consistent executive satisfaction and 90-day renewal/expansion tracking
• Weekly playbook and process improvements based on field learnings

Location & Schedule

Remote role open to candidates in LATAM, Africa, and Eastern Europe. Must be available during US business hours aligned with client time zones.