Beyond the Work

The fuller picture.

A quarter-century of enterprise work sits on top of a life shaped by other environments, cities, oceans, air, and ideas. A short field guide.

Timeline

Atlanta to Greenville, by way of the Pacific, the Keys, and Barcelona.

Atlanta · Birth
Origin, Georgia
Born in Atlanta in the early 1980s. At roughly eighteen months old, the family relocated to Raleigh, North Carolina.
Raleigh · Childhood through 1996
North Carolina, Research Triangle
Raised in the Research Triangle during the formative years. Early exposure to personal computing, programming, and technology sparked a lifelong fascination with systems, engineering, and innovation.
Portland & Vancouver, WA · 1984–Present
Pacific Northwest, Second Home
A second home throughout my life. Through family, consistent summers, holidays, and extended stretches in the Pacific Northwest since childhood, a lifelong connection to the region's culture, landscapes, and outdoor lifestyle.
Greenville, SC · 1996–2002
Middle and High School
Completed middle school and high school in Greenville. These years established many of the personal relationships and values that continue to shape my perspective.
Florida · 2002–2004
Adult Life Begins
Began adult life and an early professional career, the transition into independence and new opportunities.
San Francisco · 2004–2010
Silicon Valley, Career Foundation
Built a career in technology during the rise of Silicon Valley, working across startups and enterprise organizations while developing expertise in product management, data, and emerging technologies.
Key West, FL · 2009–2010
Technical Diving, GUE / DIR
A pivotal chapter centered on technical diving and underwater exploration. Expanded expertise through Global Underwater Explorers (GUE) and Doing It Right (DIR) methodologies: disciplined team-based diving, advanced technical procedures, gas blending, dive-site logistics, and underwater grid establishment supporting marine and archaeological survey work. Reinforced a systems-oriented approach to planning, precision, risk management, and execution that still shapes the work today.
Los Angeles · 2010–2012
Southern California
Expanded experience across technology, digital products, consulting, and strategic partnerships while growing a professional network throughout Southern California.
Asheville, NC · 2012–2020
NOAA and Old North
Worked with NOAA while founding and growing Old North, balancing public-sector technology with entrepreneurship, branding, and creative pursuits.
Greenville, SC · 2021–2023
Enterprise Partnerships
Focused on enterprise technology partnerships and strategic business development while preparing for an international move.
Barcelona · 2023–2026
International Perspective
Lived and worked in Barcelona, gaining an international perspective while focusing on enterprise AI, strategic alliances, and long-term product innovation.
Greenville, SC · 2026–Present
· You are here
Enterprise AI and CastleGate
Current base of operations. Focused on enterprise AI partnerships while developing CastleGate, an AI-native platform for enterprise governance, continuity, and intelligent software delivery. A synthesis of years across technology, partnerships, entrepreneurship, and systems thinking into a long-term vision for enterprise software.

San Francisco

San Francisco, During the Dot-Coms

Arrived in San Francisco on an invitation to interview at Telephia (later acquired by Nielsen). Within months, found myself immersed in Silicon Valley's momentum during its defining era.

Grew up in Portland, later Marin. San Francisco, arriving after both, felt like home immediately. Still does. Something missed every day since.

A lone figure on the shoreline beneath the Golden Gate Bridge, wrapped in San Francisco fog. — Golden Gate · Fog

On the ground

The Mediterranean

The Mediterranean, taken as a whole, is the region that most consistently shapes my life and interests. Iberia and the Balkans, the Maghreb and the Levant, the Adriatic and the Aegean, Türkiye and the islands in between. Different operating cultures, different assumptions about how organizations and cities should be built, and a useful reminder that most "best practices" are local defaults dressed up as universal truths.

Day to day I move through Spain, Portugal, Morocco, Malta, Türkiye, and the Balkans, with regular passes through Belgium, the Netherlands, and Germany on the way in and out. A rotation that keeps the work grounded in more than one market's assumptions and makes the contrasts between operating cultures impossible to ignore.

For the last three years I've held both Spanish and Portuguese residency, which turned Iberia from a travel destination into a second operating base and an anchor for the wider region. Next up: a Balkans trip this fall, deeper time in North Africa and Türkiye, and, a little further out, a stone home in Sicily in 2027. Lemon trees and artichokes included.

Creative practice · Spain

Tiger Studio

Time in Spain has also been a dedicated study of creative practice, working alongside a network of creatives to launch several ventures, including Tiger Studio, a graphics and brand incubator building foundational brands for policy work and cross-industry ventures, developed with a range of global partners.

Aerial view of Barcelona at dusk, the Eixample grid running to the Mediterranean, Montjuïc and the port to the right. — Barcelona · Eixample

Jack Roche at the winch of a sailboat in heavy weather, spray across the deck, grey ocean behind. — Offshore · Blue water

Sailing

Captain since 2019. Two ocean crossings. ~15,000 nm logged.

USCG captain's license since 2019. ASA-certified through levels 101-114, Basic Keelboat through Advanced Coastal Cruising and Offshore Passagemaking. Roughly fifteen thousand nautical miles as captain and first mate, including two ocean crossings.

Started in San Francisco beer-can racing on the Bay, moved down to Baja runs, then into Caribbean-to-North Atlantic delivery work, moving other people's boats across real water on real schedules. Circumnavigation planned within five years.

Preferred blue-water platform is a Hans Christian 40. A 50- footer comes later for Mediterranean cruising. Active interest in cold-water passage-making and aluminum hull construction, the boats built to go where the weather isn't optional.

I sail solo often enough to take it seriously. There's no backup out there, just preparation, judgment, and the willingness to be fully responsible for the outcome. It's not a metaphor I reach for lightly, but the discipline maps directly onto how I think about building systems that have to hold up without someone standing over them.

Certifications & Training

ASA credentials and dates

Chronological

2005
2010
2010
2018
2018
2018
2018
2018
2018

Tap a milestone to view details. Scroll horizontally on smaller screens.

All credentials

ASA 101 through 114, Basic Keelboat through Advanced Coastal Cruising, Offshore Passagemaking, and Cruising Catamaran.

Professional credential

RYA Yachtmaster®

Started in 2026 · In Progress

The RYA Yachtmaster® Certificate of Competence is widely regarded as one of the world's most respected sailing qualifications. Unlike most certifications, it is not earned through course completion alone. Candidates must demonstrate extensive sea time, advanced navigation, seamanship, boat handling, and command ability during an independent practical examination.

I began the Yachtmaster pathway in 2026 as part of a long-term commitment to offshore sailing, seamanship, and professional development at sea. The goal is to earn the RYA Yachtmaster Offshore Certificate of Competence, continuing beyond my existing ASA certifications and offshore passage-making experience.

RYA

Yachtmaster® Offshore

In Progress

Started: 2026
Current: In Progress
Target: RYA Yachtmaster Offshore
Focus: Offshore seamanship, navigation, command, and passage making

Aviation

Vero Beach, 2009, and the Cessna I ended up owning.

Private Pilot training, roughly 80% or more complete, never finished the certificate. Trained at FlightSafety Academy in Vero Beach, Florida, in 2009-2010, on a Cessna 172. Extensive cross-country flying, touch-and-goes until the pattern felt like muscle memory, and enough radio work to stop sounding like a student on the frequency.

I later bought that same 172 into fractional ownership - the airplane I trained on became the airplane I flew. Finishing the private pilot certificate, and eventually an instrument rating, is still on the list.

General aviation is the clearest version of the same discipline that runs through the rest of my work: real checklists, real weather, real consequences. Nothing about it rewards improvisation.

Jack Roche at the controls of a Cessna 172 in flight, headset on, lakes and coastline visible through the windscreen. — Cessna 172 · VFR

Underwater

Diving

Divers descending on a large shipwreck in blue water, bubble columns rising from the deck. — Wreck · Descent line

Looking up the hull of a sunken vessel with divers silhouetted against the surface light. — Hull · Surface light

Technical diver in a twinset configuration finning along a wreck at depth. — Twinset · Technical

Over 5,000 logged dives. PADI Divemaster with GUE (Global Underwater Explorers) Technical Fundamentals, PADI Gas Blender, TDI (Technical Diving International) Rescue Diver, and GUE / NAUI (National Association of Underwater Instructors) Cavern Diver certifications earned in Mexico.

Spent several years diving professionally, teaching both recreational and advanced wreck and technical deep diving. In 2009, contracted through Blue Ocean Sailing on a Mel Fisher's Treasures project, running side-scan sonar surveys, grid laying, and technical site assessment, sponsored by the Busch Family Endowment, with data work supporting National Geographic.

Same underlying requirement as the flying and the sailing: rigorous protocol, real certification standards, zero tolerance for skipping steps. The stakes are physical instead of organizational, but the operating instinct transfers cleanly.