Independent advisory · San José, Costa Rica · see deeply.

Guillermo Sandí

I help mid-market and enterprise organizations in LATAM make better licensing and cloud decisions, and pay only for what they actually use.

01 — What I do

Licensing advisory, not license resale.

Twenty years on the commercial side taught me where to look. Today I look from the buyer’s side.

Software Asset Management (SAM)

Inventory, usage rights, and real licensing position. Know what you have, what you use, and what you lack before sitting down to renew.

Cloud economics

A reading of cloud spend against real consumption. Where commitment exceeds use and where the licensing model no longer fits.

Contracting and negotiation

EA, MPSA, MACC, CSP. Renewal preparation and closing discipline — T-minus, T-36 — from the buyer’s side, not the vendor’s.

Multi-vendor advisory

Licensing optimization beyond a single manufacturer. Independent judgment with no quota to defend at the table.

02 — Record

The record, without inflation.

Figures from a complete Microsoft licensing cycle in the region’s large markets.

Deep Sight metrics panel: fiscal years over quota, attainment, cloud consumption, NSAT, partners, and Puerto Rico.

✓ Figures verified against Guillermo’s own record
FY13 110% · FY14 122% YTD · NSAT 195 FY13 & FY14 (#1 LATAM) · Puerto Rico +97% YoY growth.

03 — Trajectory

Twenty years learning the other side of the table.

From emerging-market coverage to licensing cycles across 41 territories in the Americas — eight countries in North and Central America, thirteen in South America, and twenty in the Caribbean.

+20 years — Technology sales and marketing

Two decades in the industry, learning how licenses are bought and sold before learning to question that motion.

10 years · Microsoft — Multi-country coverage, Americas

Costa Rica as operating base, with extended coverage across LATAM emerging markets — Central America, the English- and French-speaking Caribbean, and island dependencies of the United States, United Kingdom, and Netherlands.

5 years · Commercial Executive — Microsoft licensing cycle

The region’s top markets: Mexico, Brazil, Argentina, Chile, Uruguay, and Colombia — plus support coverage for Peru, Ecuador, and Venezuela.

2012 · Puerto Rico — Licensing Sales Specialist

Relocated from Costa Rica to Puerto Rico to hold the licensing specialist role in the island market.

Today · San José — Principal, Deep Sight Consulting

Independent advisory for CIOs, CISOs, and CFOs at mid-market and enterprise organizations across LATAM.

Territory coverage · 41 territories

Territory coverage across 41 territories — Territory coverage modeled as an NGC 4038/4039 galactic collision: Central America, South America, and a tidal arm toward the Caribbean.

04 — Capabilities · 2024 → present

From zero to an agent system in production.

In October 2024 I started programming from zero. Eighteen months later I operate my own agent system.

I build the agents I advise on.

It is the bridge between twenty years of licensing and the way I work today — an advisor who automates his own analysis, research, and due diligence. Deep Sight’s GaaS thesis, made practical.

Aug 2024

Deliberate model practice: systematic evaluation of ChatGPT, Gemini, Claude, DeepSeek, and Perplexity.

Oct 2024

Python from zero, with VS Code and PowerShell from day one; local-agent experiments on GPU.

Sep 2025

First real scripts: GPU transcription pipeline. Migrated from NeMo to faster-whisper/CUDA — same task, simpler architecture.

2026

Agent engineering: RAG, multi-agent, structured output. NotebookLM → Claude Code → Obsidian system in production.

Current stack

AI / Agents · Python · PowerShell · VS Code · Obsidian

AI / Agents I operate a personal agentic system: prompt engineering, custom commands and skills, and a voice interface — speech-to-text and text-to-speech — behind security guardrails.
Python Custom multi-engine toolkit: profiling and confidence scoring, ingestion, GPU transcription, and a RAG voice assistant. Not loose scripts — shared design principles: confidence routing, read-only source, append-only brain.
Obsidian Knowledge architecture at scale: 110 permanent notes, 174 ingested research notebooks, 4,000+ conversations in navigable maps, and 15 indexes.
Design principles Read-only system of record · Append-only brain · Confidence over hard rules · Controlled vocabulary, not NER · Two-stage gated pipeline.

05 — Credentials

Training that connects licensing, negotiation, and networks.

MS 70-705 — Designing and Providing Licensing Solutions to Large Organizations

Certified Licensing Specialist · Pearson VUE.

Oracle LMS — Oracle License Management Services

Partner’s Technical Champion.

Schranner — Schranner Negotiation Institute

In-house negotiation program.

Cisco CCNA — Cisco Certified Network Associate

Cisco Systems Networking Academy.

06 — Contact

Let’s talk

Current contact details, operating notes, and the verified email form live on Contact.

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