HCThe Hess Collective
Built with purpose. Led by experience.

Ideas, ventures,
and work that endures.

The Hess Collective brings together technology advisory, talent and business development, publishing, and creative ventures under one family-led company.

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EST.2026
01 — Our Story

A shared point of view

Experience gives an idea weight.
Curiosity gives it momentum.

Founded by Brent and October Hess, The Hess Collective is a home for work shaped by practical experience, thoughtful execution, and the belief that how you approach a challenge matters.

We connect people, technology, and opportunity—helping businesses make stronger decisions, build meaningful relationships, and turn good ideas into durable results.

BPhoto coming soon

Brent Hess

Technology advisor · Builder · Author

Brent is an enterprise technology advisor and architect whose work spans cloud transformation, managed services, Microsoft platforms, infrastructure, AI-enabled operations, and client strategy. He brings technical depth together with an executive perspective, helping organizations turn complex environments into clear roadmaps and practical outcomes. He is also an author and builder of digital products focused on making ideas more useful and accessible.

LinkedIn profile · Coming soon
OPhoto coming soon

October Hess

Recruiter · Business development leader · Connector

October is a relationship-driven recruiting and business development professional with a talent for connecting people, opportunities, and organizations. Her work centers on understanding what businesses truly need, cultivating trusted relationships, and helping the right people find the right place to contribute. Her complete professional biography and career highlights will be added in the next update.

LinkedIn profile · Coming soon
02 — The Collective

What we build

Distinct ventures.
One standard.

Each part of the collective begins with a useful idea and is built with clarity, care, and a bias toward action.

01
A

Technology Advisory

Strategic guidance for organizations navigating cloud, infrastructure, managed services, AI, and enterprise transformation.

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02
T

Talent & Growth

Recruiting, relationship development, and business-growth support built around finding the right people and creating the right opportunities.

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03
P

Publishing & Ideas

Books, frameworks, and practical thinking designed to help people lead, communicate, and solve problems more effectively.

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04
D

Digital Ventures

Useful, human-centered products that transform complex information into clear and intuitive experiences.

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03 — Expertise

Two disciplines. One advantage.

Connecting strategy, technology, and people.

Brent and October bring complementary strengths to the collective: deep technical and advisory experience paired with relationship-led recruiting and business development.

01

Technology Strategy

Roadmaps, modernization planning, architecture, and executive decision support.

02

Cloud & Managed Services

Azure, AWS, Microsoft 365, infrastructure, resilience, governance, and service optimization.

03

Recruiting & Talent Strategy

Relationship-centered recruiting, candidate engagement, talent alignment, and workforce growth.

04

Business Development

Partnership cultivation, opportunity development, client relationships, and strategic growth.

05

AI-Enabled Transformation

Practical use cases, workflow automation, adoption planning, and responsible implementation.

04 — Selected Work
Cover of It’s All About The Approach: Shaping Your Life, One Choice at a Time by Brent M. Hess

Book · Leadership & Communication

It’s All About
The Approach

Shaping Your Life, One Choice at a Time. A practical framework for approaching conversations, leadership moments, and everyday challenges with greater intention.

View on Amazon
TripCraft mobile travel app created for Brent and October’s 2026 Europe trip, showing the live dashboard, city guide, and route through Italy and Spain

Built for our Europe tripSorrento → Rome → Seville → Córdoba → Madrid

Custom Travel Experience · TripCraft

Your whole trip.
One personal command center.

TripCraft turns scattered confirmations, reservations, maps, ideas, and day-by-day plans into one home-screen-ready mobile companion—designed around where you’re going and how you want to travel.

01

Live trip mode A departure countdown, current-city travel hub, auto-updating Today card, and the next action you need at a glance.

02

Complete daily agenda Every travel day, hotel, activity, transfer, and flexible moment organized in one clear itinerary.

03

Flights and transportation Routes, times, terminals, seats, baggage, layovers, rail details, private transfers, arrival plans, and live flight-status links.

04

Personal city concierge One-tap maps, attractions, restaurants, hotel-area suggestions, and a ready-made “Tonight” plan for every stop.

05

Weather and local know-how Destination forecasts, quick currency guidance, and useful Italian and Spanish phrases while you’re on the move.

06

Safety and essentials Emergency numbers, embassy information, passport reminders, current-hotel details, and important travel contacts.

07

Moments worth remembering Date-night ideas, food and photo challenges, favorite-dish ratings, and a trip-memory checklist.

08

Easy finish and return home A practical departure checklist for passports, chargers, AirTags, souvenirs, and boarding passes.

Planning a future trip? We can talk through your destinations, travel style, priorities, and reservations—then shape a TripCraft experience around your journey.

Let’s talk about your trip
ASSESSALIGNADVANCE

Framework · Enterprise Services

From complexity to clarity

Operational frameworks that turn business and technology strategy into measurable outcomes.

05 — Study Tools

Interactive learning

Practice with purpose.

Focused, scenario-based exam preparation built to strengthen technical judgment—not just memorization.

60 questions · 100 minutes

MD-102 Mock Exam

Microsoft Intune, endpoint security, application deployment, device management, automation, monitoring, and reporting.

Start the exam 30 questions · 50 minutes

Datadog Fundamentals

Agent configuration, integrations, metrics, tagging, dashboards, monitors, logs, tracing, and synthetic testing.

Start the quiz
06 — What Partners Value
“A rare combination of strategic perspective, technical credibility, and a genuine ability to build relationships that move work forward.”

Client testimonial · Full attribution coming soon

Trusted adviceHuman connectionPractical execution

Let’s build something worthwhile

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conversation.

Have a business challenge, a talent need, a partnership idea, or a venture worth exploring? Tell us what you’re thinking.

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