Welcome to my corner of the internet

I'm Zachary.

I build revenue engines for SaaS and AI companies in eCommerce. From zero to $3M+, from founding AE to scaling teams across two continents.

When I'm not closing enterprise deals or architecting go-to-market strategies, you'll find me analyzing charts, grinding ranked matches, or hunting for the perfect pour-over.

Trading Gaming Chilling
Read my story Let's talk
The Origin

I learned to build in basements

Before the fancy titles, I was just a kid with hustle and a laptop. These two exits taught me everything that matters.

Starting Item — 2012
Expand Your Roots
Supplements out of a basement. No brand, no budget, just hustle. Landed the Mutant exclusive. Became #1 in Canada.
Exit Complete
Starting Item — 2013
Zero-Value Inc
Zero dollars, zero connections. Just me and a laptop. 60 days to $30K MRR. Scaled it, sold it, moved on.
Acquired
The Pivot

Then I got curious about markets

Those basements taught me I could build. But I became obsessed with why some businesses scale and others die.

Not just stock charts — the mechanics of growth. That obsession pulled me from analyzing crypto at eToro to building revenue engines from scratch at startups.

Been the first AE hire twice. Taken products nobody knew existed to $3M+ ARR. Closed enterprise deals across US and LATAM that others swore were dead ends.

Career Stats
2007 — PRESENT
Years in the game 10+
Founding AE roles 2x
Revenue generated $3M+
Successful exits 2
TOTAL VALUE PRICELESS
ZC-2026-EXIT
THANK YOU FOR READING
The Journey

How the basement kid became an enterprise AE

$ZACH EQUITY
Price
$3.2M
Change
12,400%
High
$3.2M
$3.0M
$2.0M
$1.0M
$0
2012
2013
2017
2018
2022
2023
2012 2014 2016 2018 2020 2022 2024 2026
Click points to explore
The Loadout

Class setup: Enterprise AE

Primary Weapon
Enterprise Sales
Full-cycle B2B sales with focus on SaaS and AI products. From first touch to close, handling complex stakeholder dynamics across US and LATAM markets.
$3M+ Generated
400+ Accounts
2 Continents
Secondary
GTM Strategy
Building playbooks from zero. Market expansion, positioning, and revenue architecture.
Founding Team
2x Deployed
Perk 1
LATAM Markets
Regional expertise. Cultural fluency, local networks, and expansion execution.
Regional Specialization
Perk 2
AI / eCommerce
Deep domain knowledge selling AI tools to online sellers and enterprise eCommerce.
Domain Expert
Perk 3
Partnerships
Strategic alliance building. Channel sales, integrations, and ecosystem development.
Relationship Builder
Tactical
Financial Analysis
CFA Level 1 & 2. Market analysis, modeling, and data-driven decision making.
CFA L1 & L2
Side Quests

Advisory Board

Helping founders architect GTM strategy and revenue engines.

Octane AI
GTM Strategy
AI / eCommerce
Smartr Subscriptions
Revenue Architecture
Retention
Northern Commerce
Enterprise Sales
Canadian Market
253 Media
Service Expansion
Agency
Out Of The Blue AI
Sales Playbook
AI Automation
The Next Chapter

What's next?

Always hunting the next thing. Building something in SaaS, AI, or eCommerce? Let's talk.

EMAIL zach.chester@gmail.com PHONE 204.260.0004 LINKEDIN linkedin.com/in/zchester
LOCATION Winnipeg, MB