UpShift Collective × Hilton Grand Vacations

Technical AI Enablement Program

From fluent to fearless. Five Fridays. A focused SLT activation sprint built for the Hilton Grand Vacations technical leadership team.

Hands-on in your HGV sandbox. Anchored by a capstone hackathon and Demo Day.

01 — What we heard

Training that meets your team at their level

Senior, technical, skeptical

Your leaders have a decade or more in systems, operations, and development. Generic AI training loses that room in the first hour.

Built in your environment

Every session runs against a real sandbox on your own stack. Skills transfer to production, not to a demo.

Your use cases, not generic ones

The curriculum is scoped to hospitality operations and P&L scenarios specific to HGV.

02 — Program at a glance

Program at a glance

Audience
~10 technical SLT
Pre-work
3 hrs of diagnostic interviews before Friday 1
Format
Five Friday virtual sessions, 3–4 hours each, plus structured homework on the Section AI platform
Cadence
Five Fridays, mid-June start (US ET / MT)
Environment
HGV sandbox on Azure and Databricks — not localhost
Stack
Azure AI Foundry, Databricks Agents & Genies, Cursor, Claude Code & CoWork
Use case focus
HGV hospitality operations and P&L workflows
Delivered by
Senior AI specialists with a Big Four–caliber engineering bench
Total commitment
~33–36 hours over the sprint
03 — Who delivers this

Led by senior technical specialists, not generalists

The calibre of the person at the front of the room is the single biggest predictor of whether technical training lands.

  • More than a decade in enterprise systems, operations, and software development
  • The technical depth you would expect from a top-tier global consulting and engineering practice
  • Fluency in real AI deployment: architecture, integration patterns, and production guardrails
  • A working command of AI economics, budgeting, and build-versus-buy decisions
  • The credibility to challenge and be challenged by senior engineers
"Practitioners who can talk the talk with your technical people, sit inside your stack, and turn AI from a buzzword into a deployment plan your team can run."
04 — The five-Friday sprint

The five-Friday curriculum

WEEK 1Foundation — Frame, govern, discover

  • AI strategy and the CTO mandate: where HGV is and where it is going
  • Governance frameworks — NIST AI RMF, EU AI Act, HGV's policy stack. Each leader leaves with a one-page governance template for their function
  • Token economics and cost defense at HGV scale, hands-on with Azure Cost Management
  • Use case discovery: each leader brings 2–3 hospitality or P&L candidates and selects one to build across the sprint
  • Homework: document the chosen workflow and sketch the agent architecture

WEEK 2Build — The stack, hands-on

  • The four-pillar stack: Azure AI Foundry, Databricks Agents & Genies, Cursor for devs, Claude Code & CoWork for business and product
  • Hands-on Foundry: provision a project, deploy a model, ground an agent on HGV sandbox data
  • Databricks Agents & Genies: lakehouse-native RAG and Mosaic AI essentials
  • First working agent shipped to the HGV sandbox by end of day — not localhost
  • Homework: build out the workflow agent on the Section platform

WEEK 3Clinic — Guided build, identity foundations

  • Live build clinic: each leader works on their chosen agent in small groups of three with the engineering bench coaching
  • Identity and Entra ID for agents: authentication, least-privilege patterns, audit trails
  • Data classification and customer data handling — sets the foundation for the CISO session
  • Multi-agent orchestration patterns: practical introduction, when and why
  • Homework: finish the agent build and prep for capstone team formation

WEEK 4Secure — CISO red-team, production readiness

  • CISO red-team session: 90-minute deep dive on the questions your CISO will actually ask — permissions, prompt injection, data exfiltration
  • Production readiness: observability, evaluation, red-teaming, incident response
  • Cost optimization at scale: model selection, batching, open-source hosting tradeoffs
  • Cloud and CoWork security at scale: audit trails and governance dashboards
  • Homework: team formation and capstone agent dress rehearsal

WEEK 5Capstone — Hackathon and Demo Day (~6–7 hrs)

  • Three teams of three (plus pairs), each taking one discovered hospitality or P&L workflow
  • Sandbox build day with the engineering bench coaching in the room — working agent shipped to HGV's Azure or Databricks sandbox
  • Demo Day to the CTO, Evgeny, and CISO
  • Winning agent earns a sponsored Phase 1 production deployment
  • Phase 1 deployment plans handed in by each leader for their function
05 — What your leaders walk away with

Outcomes

  • Working agent shipped to HGV's sandbox on Azure or Databricks
  • Governance memo for their function — NIST, EU AI Act, and HGV-aligned
  • Cost-control framework defendable to the CFO and CISO
  • Ability to shepherd their team through AI decisions and speak the language with confidence
  • Phase 1 deployment plan with three or more prioritized use cases
  • Sponsored production deployment for the winning capstone agent
06 — Investment

Investment

$4,000
per participant

Five-Friday custom sprint, live virtual delivery, dedicated sandbox, senior specialist-led, scoped to HGV hospitality and P&L use cases.

Final cohort total confirms once the roster is locked. Any third-party platform or licensing costs, if introduced, are billed separately and disclosed in advance.

Let's get the dates on the calendar.

Five Fridays from mid-June. We are ready to meet your team where they are.

Scott Walker
Founder and CEO, UpShift Collective
scott@upshiftcollective.com
Book a time

Questions? Email scott@upshiftcollective.com.