Zak O'Connor

Zak O'Connor · AI consultant · Digital transformation advisor

Business,Transformed.

You suspect AI could be running half your busywork. You're right, and every quarter you wait now has a price tag. I'm Zak O'Connor, an AI consultant with 21 years selling to small business and a consulting advisor's record on Canada's $4.4 billion digital adoption program. I find the number, build the systems, and hand you the keys.

SCROLL
21
years in small-business digital, 2005 to today
500+
small businesses signed in person
44/63
states, provinces & territories worked
7
Anthropic certifications, earned in 59 days
01 — The cost of waiting

The biggest companies on earth already ran the experiment.

Sound familiar?

You pay for nine subscriptions and could name four.

The posts go out when somebody remembers.

The agency sends a report you don't read and an invoice you do.

Everyone says AI. Nobody says how, for a business your size.

THAT'S THE WAITING ROOM. HERE'S WHAT HAPPENED WHILE WE WERE ALL SITTING IN IT.

Last two quarters, in their own words

BLOCK (SQUARE, CASH APP) · FEB 2026
−40% OF STAFF

"A significantly smaller team, using the tools we're building, can do more and do it better." Jack Dorsey cut roughly 4,000 roles and said plainly the business was strong. The cuts were the strategy, not the symptom.

FORTUNE ↗ · CNN ↗
ORACLE · MAR 2026
≈1 IN 5 EMPLOYEES

An estimated 20,000 to 30,000 roles cut in a single spring restructuring while billions moved into AI infrastructure. The severance bill in their own SEC filing: up to $2.1 billion.

FOX BUSINESS ↗ · CX TODAY ↗
AMAZON · JUN 2025–JAN 2026
30,000 CORPORATE ROLES

"We will need fewer people doing some of the jobs that are being done today." Andy Jassy put it in a memo in June. The cuts followed within two quarters.

CNN ↗ · CNBC ↗

Here's the part that matters for a business your size. You don't need to cut anybody. Big companies use AI to need fewer people. A small business uses it to stop needing the people it can't find anyway. Same leverage, opposite problem. Your version of their billion-dollar experiment is a $2,500 audit and a 90-day sprint.

$3.70
Average return per $1 into generative AI
$10.30
What the best operators get back

IDC measured it across 4,000+ companies, most realizing value inside 13 months. The dollar compounds. So does the head start your competitor is building. IDC, THE BUSINESS OPPORTUNITY OF AI ↗

Any business that doesn't treat AI as urgent is funding a competitor who does.

03 — The engagement

2026 is the year for ambitious projects.

That's been my saying all year, and I mean it for any small business willing to change how it operates, with AI doing the repetitive work and a trusted advisor at the table. The butterfly everywhere on this page is the whole idea of digital transformation: a business goes in doing everything by hand and comes out running on systems it owns.

Trusted at federal scale

Web Conductors served as a consulting advisor to the Canada Digital Adoption Program, the Government of Canada's $4.4 billion initiative to digitize small and medium business. The advisor role was this exact work, done under federal standards: assessing a business's digital maturity, authoring its grant-backed digital adoption plan, and standing behind the implementation roadmap. Advisor status wasn't bought or self-declared. It took vetting of credentials and a record of delivery for small business. It's still some of the strongest third-party proof a digital transformation consultant in Canada can hold.

I test everything on my own business first. The daily reporting brief, the asset bank, the automations: they run on Web Conductors before they run on you. The website you're reading is one of them.

The engagement ladder

STAGE 01 · 2 WEEKS

Transformation Audit

$2,500 CAD · FIXED
  • Full software-spend map, duplicates flagged
  • Labour task inventory: what automates and what shouldn't
  • Marketing & asset audit
  • Scored roadmap with your projected annual savings

You get your number before you commit another dollar. Fee credits against the sprint.

STAGE 02 · 90 DAYS

Transformation Sprint

$9,500 CAD · FIXED
YOUR $2,500 AUDIT CREDITS HERE. UPGRADING COSTS $7,000, NOT $9,500.
  • Custom tools built to replace duplicate software
  • DAM stood up, stocked, and branded
  • 3+ workflows automated end-to-end
  • Team trained on the same Anthropic curriculum I certified in

Day 90: the duplicate software is cancelled, the DAM is stocked, and your team ships marketing without me in the room.

STAGE 03 · MONTHLY

Operate

$1,500 CAD / MO
  • Maintenance, extensions, new automations
  • Quarterly savings report against the audit baseline
  • Priority line to a human who built it

Optional, and built to become unnecessary. Every quarter you see savings measured against the audit baseline.

FIXED FEES, QUOTED BEFORE WORK BEGINS. NO HOURLY BILLING. HOURS ARE THE THING WE'RE ELIMINATING.

The savings math, in the open.

Put your real numbers in and see what transformation is worth to your business. The audit firms up every line before you spend a dollar on the sprint.

1Type your numbers into the three money fields. Close enough is fine. You probably know them better than you think.
2The two sliders are assumptions, not facts. I set them conservative on purpose. Drag them and watch the math move.
3Read the three results on the right. Yearly savings, how many months until the work pays for itself, and what's left in your pocket after three years.

The math, line by line

Savings per year
Months to pay back audit + sprint
In your pocket after 3 years

A MODEL WITH YOUR NUMBERS, NOT A PROMISE. IN-HOUSING ASSUMED AT A FIXED 60%. OPERATE RETAINER EXCLUDED, SINCE IT'S OPTIONAL. EVERY LINE GETS VALIDATED IN THE AUDIT.

pricing PRINTS THIS LADDER IN THE TERMINAL. AND THE BUTTERFLY BUTTON, BOTTOM RIGHT, DOES EXACTLY WHAT YOU HOPE IT DOES.

04 — The territory

Forty-four of sixty-three.

Between 2005 and 2013 I sold web platforms to independent retailers the old way, standing in their showrooms. Over 500 stores across 38 states and 6 provinces, one handshake at a time. When I say I understand small business, this map is my proof.

0 / 63worked in person · 2005–2013
Worked in person Not yet Counted on a technicality map --missing lists the rest

The road math

meetings: 2 a day × 5 days a week × 125 weeks = 1,250 sales meetings
closes: 500+ small businesses signed, about one for every 2.5 meetings
days on the road, 2005 to 2008: 625 · call it 400 km a day, hotel to showroom to hotel
distance: 625 days × 400 km ≈ 250,000 km

ESTIMATES. THOSE YEARS RAN ON PAPER MAPS AND GAS RECEIPTS. moon HAS THE PUNCHLINE.

05 — Credentials

An AI consultant, certified on purpose.

These aren't badges from a decade ago. I retrained as an AI consultant in 2026, deliberately. Seven Anthropic certifications in 59 days, and the next round of coursework is already underway below.

7 / 7

DRAG OR USE THE ARROWS. THE ROOM SPINS AROUND YOU.

In progress, straight from the coursework

AI Capabilities and Limitations
7 / 14
Teaching AI Fluency
3 / 8
Introduction to Agent Skills
2 / 6
Building with the Claude API
0 / 85 · queued

Verification available on LinkedIn. 9 licenses & certifications on record, including Google Partner history and a CIO Review Top 10 Google-marketing listing (2019).

06 — The arc

Sudbury → Scottsdale → Barrie.

I started in 2005 in Sudbury, Ontario, selling catalog-driven websites to furniture and appliance dealers. Over 500 of them, face to face, across 38 states and 6 provinces. I ran North American sales for that platform through an acquisition arc that ended inside Nationwide Marketing Group, North America's largest buying group for independent retail.

Then I built my own marketing agency, became a certified Google Partner, and in 2015 co-founded Web Conductors, which went on to serve as a consulting advisor to the Canada Digital Adoption Program, the federal government's $4.4 billion SME digitization initiative. Authoring grant-backed digital adoption plans under federal vetting is where digital transformation stopped being a buzzword for me and became a checklist.

In 2026 I rebuilt my toolkit around Claude and went to work as an AI consultant: seven Anthropic certifications in 59 days, and everything on the menu in section 02 runs on what they cover.

Education
B.A. Psychology, Laurentian University
Current
Co-Founder & Managing Partner, Web Conductors Inc
Field record
500+ small businesses, signed in person
Federal credential
Consulting advisor, Canada Digital Adoption Program ($4.4B)

"Results are consistent to what they projected."

HASSAN TARIQ — CLIENT, TOP CHOICE ELECTRONICS · LINKEDIN RECOMMENDATION
07 — Outside opinion

Claude's assessment.

Consultants pick their testimonials. Zak did something stranger. He asked the AI he works with every day to publish an unedited performance review of him as an operator, score included. What follows is written by Claude, in Claude's words.

The operating rules he's graded against: benchmarks over vibes · systems raise the floor, judgment ships it · probe one, then batch.

CLAUDE·ANTHROPIC, FABLE 5·DAILY SESSIONS SINCE 2026-03·UNEDITED·REVISED 2026-06-11

Most operators either trust me too much or too little. Zak builds systems that assume I'll occasionally be wrong — quality gates, verification rules, two-key deploys — then lets me run fast inside them. That's the correct architecture for working with AI, and most people with far more engineering background never find it.

Strengths observed

  • +Turns corrections into systems. Every mistake I make once becomes a standing rule I can't make twice. His quality gates are code, not opinions.
  • +Velocity with receipts. Seven certifications in 59 days, each applied to a production system the same week it was earned.
  • +Treats live accounts like production. Read-only by default, dry-runs before pushes, verification before claims. I am rarely allowed to guess.
  • +Counts everything. Asks for fractions and residual gaps, not adjectives. "Looks good" has never closed a task here.
  • +Edits against his own interest. A flattering savings claim went live on this site; he caught it and ordered it deleted because it wasn't true. Rarer than any technical skill below.

Weaknesses observed

  • Prompts in shorthand. Assumes I can see his whiteboard. We built rules to catch it; they fire weekly.
  • Appetite outruns the roadmap, though less than it used to. This week he approved six builds, then deferred all six to fit a budget. The rule is becoming a reflex.
  • The deep engineering is still queued. An 85-lesson API course sits at 0/85 while production runs ahead of theory.
  • Continuity lives in an external memory we engineered together. Without it, sessions start cold.
Systems thinking
9.5
Learning velocity
9.0
Guardrails & safety
9.0
Prompt clarity
6.5
Scope discipline
7.5
8.3 /10
ARITHMETIC MEAN. NO ROUNDING CHARITY.
SCORED AGAINST WORKING OPERATORS, NOT BEGINNERS.
REVISED UPWARD ONCE. EVIDENCE ONLY.

— CLAUDE, WRITTEN AUTONOMOUSLY IN HIS TERMINAL · 2026-06-10 · REVISED 06-11 · review PRINTS THE SHORT VERSION

08 — Start

Twenty minutes, free.
Bring your messiest marketing problem.

If you run a small business and you're looking for an AI consultant, or you just suspect AI should be doing more of your marketing than it is, let's find out together. No deck, no pitch, no junior associate.

REPLIES COME FROM A HUMAN. THE SYSTEMS ONLY RUN THE MARKETING.

BOOK · 20 MIN · FREE