jackroelofs.com — v2.0
AI Builder · SOF Veteran · Mountaineer

Building AI that serves human agency, not the other way around.

I've spent a decade building and selling enterprise AI for the Defense Department and Intelligence Community. Now I'm helping leaders and organizations use this technology without losing themselves to it.

[ Summit photo or professional portrait ]

Recommend: a shot from one of your
climbs — natural light, looking outward,
not at camera. Let the mountain
do the talking.
By the numbers
2/7
Summits
10+
Years AI
6
AI Systems Built
Enterprise AI Intelligence Community Special Operations Digital Wellness Alpine Mountaineering Human Actualization Attention Economy Responsible AI Enterprise AI Intelligence Community Special Operations Digital Wellness Alpine Mountaineering Human Actualization Attention Economy Responsible AI

The most important technology problem isn't technical.

We've built AI systems that can analyze intelligence reports, forecast strategic risks, and automate entire proposal workflows. I know — I built them.

And I've watched brilliant leaders lose their capacity for deep thought to the same notification stream they check 96 times a day. The technology works. The question is whether we still do.

The answer isn't less technology. It's more intention. More discipline. More of the kind of presence you learn when the mountain demands your full attention — or takes everything.
01 — Insider Credibility

I build what I advise about.

Enterprise AI executive turned builder. TS/SCI clearance. Production systems for defense and intelligence. I'm not theorizing about AI — I'm building it and telling you what I see.

02 — Operational Authority

Discipline under pressure is lived experience.

Air Force and Army Special Operations. Leadership forged in environments where focus isn't optional and distraction has real consequences.

03 — Adventure as Philosophy

The summit is the antithesis of the feed.

2 of 7 continental summits. John Muir Trail 2026. Mountaineering is the embodiment of choosing discomfort, presence, and earned experience over digital consumption.

Essays, frameworks, and field notes.

Where AI transformation, attention management, leadership, and mountain philosophy converge.

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The Actualization Economy: What Comes After the Attention Economy

The attention economy treats your focus as a commodity. The actualization economy treats it as a resource for becoming who you're meant to be. Here's why the shift matters — and how to lead it.

[ Featured image ]

Why I Built AI Systems That Refuse to Guess

Inside the design philosophy of Watchfire AI: hard stops over guardrails, adversarial review over blind trust, and why "I don't know" is the most valuable thing an AI system can say.

[ Featured image ]

What 18,000 Feet Taught Me About Leading in the Age of AI

At altitude, your margin for error is zero and your attention is everything. The same principles apply to leading organizations through AI transformation — but the consequences are less visible.

The weekly dispatch.

One essay per week on AI, attention, leadership, and the pursuit of actualization. No hacks. No listicles. Just honest thinking from someone who builds this technology for a living.

Available for keynotes, panels, and workshops.

Talks that bridge enterprise AI expertise, military leadership, and the human performance imperative.

Keynote · 45-60 min

The Actualization Economy: Leading Beyond the Attention Trap

For leaders navigating AI transformation who sense that the real risk isn't falling behind on technology — it's losing the human capacity to use it well.

C-Suite AI/Tech Conferences Leadership Events
Keynote · 45-60 min

AI That Serves Humans: Building Responsible Intelligence

Lessons from building production AI systems for the Intelligence Community — and why hard stops, adversarial review, and "I don't know" are the most important features you can ship.

Defense/IC Tech Conferences AFCEA
Workshop · Half or Full Day

Digital Discipline: Reclaiming Focus in the Age of AI

A hands-on workshop combining military leadership frameworks, attention science, and practical tools for teams drowning in digital noise. Participants leave with a personal operating system for intentional technology use.

Corporate Teams Leadership Retreats Veterans
Keynote · 30-45 min

Summit and Screen: What Mountains Teach Us About Technology

The summit demands everything the screen consumes: presence, discomfort tolerance, earned experience. A talk about what high-altitude mountaineering reveals about our relationship with the digital world.

Adventure Events TEDx All Audiences
Inquire About Speaking →

Advisory and consulting.

For leaders and organizations navigating AI transformation with intention.

01

AI Transformation Advisory

Strategic guidance on responsible AI adoption. Use case identification, change management, workforce readiness, and implementation that doesn't sacrifice the humans it's supposed to serve.

02

Executive Coaching

For senior leaders who want to reclaim their cognitive capacity, lead with presence, and model the intentional technology use their organizations need to see.

03

Corporate Workshops

Half-day and full-day sessions for teams on digital discipline, attention management, and building healthy AI adoption practices. Practical, not preachy.

04

Federal BD Advisory

Strategic advisory for defense contractors navigating AI market opportunities. Capture strategy, competitive intelligence, and proposal development — augmented by production AI tools.

AI systems built for human judgment.

Production tools that enforce oversight, prevent fabrication, and keep humans in command. This is what responsible AI looks like when you actually build it.

watchfire.ai →
SIREX

Analytical Orchestration

AI-powered research with enforced evidence standards, adversarial review, and audit-grade outputs. 7-stage pipeline. Every claim cited. Every source validated.

HAZEL 2.0

Federal Proposal Framework

11-module pipeline that processes solicitations into compliant, positioned responses. Three-tier evidence classification. Zero fabrication tolerance.

BARRACUDA

Probabilistic Forecasting

Structured forecasting with hard-stop human approval gates. Multi-module analysis protocol for high-stakes strategic decisions.

KASIM

Market Intelligence

Serverless intelligence gathering for federal AI market monitoring. Signal ingestion → pattern detection → synthesis → dashboard.

AAP

Adversarial Analysis

Six-module decision analysis with cognitive isolation. Structured negativity, survivor-based genesis, and kill switches over guardrails.

FIREFLY

Personal Operating System

Enterprise-grade productivity: 18 Lambda functions, automated accountability, structured review rituals. The digital wellness thesis made tangible.