AI Strategist / Chief of Staff (Ontario)

AI Strategist / Chief of Staff (Ontario)

24 Sep
|
AMZ Prep®
|
Ontario

24 Sep

AMZ Prep®

Ontario

AMZ Prep is an Amazon-first 3PL and commerce enablement company. We run 20+ warehouses across the US and Canada, move over 200,000 units a day, and support more than 1,300 brands.

We started as a fulfillment company, but we are becoming an AI and software-first one. That shift is not a side project. We are deploying AI across the brands we work with, embedding it into how we run operations, serve clients, and grow the business. This role sits at the center of that shift.

Core Values
Our team operates on a few simple principles. If you do not align with these, we would recommend you do not apply.

Win Relentlessly. We work hard and stay resilient when the build gets ugly. We move fast, adapt when reality does not match the plan, and push to raise the bar every day.

Own the Outcome. We are responsible for what we ship, not for having tried. We do not wait for someone else to solve the problem. When something breaks in production, we step in, fix it, and make sure it does not happen twice.

Be Humbly Confident. We are confident in our work and grounded in how we treat people. We communicate directly, avoid politics and ego, and call out problems early instead of managing around them.

Obsess Over Data. Numbers decide. We measure what the system does before and after, we quantify what we saved the client, and we let the metrics tell us when something is not working.

About the job
The AI Strategist owns the relationship as we build AI solutions for the brands we work with. This role runs the discovery, finds where the money is leaking, builds the roadmap, and stays on to ship it alongside our engineering team.

You are accountable for adoption and for the brand’s outcome.

Every operator we work with has said a version of the same thing. We looked at AI, we ran a pilot, and nothing changed. The model is almost never the reason. Nobody mapped how the work actually happens, nobody owned the rollout past launch, and nobody stuck around when adoption stalled in week three. That is what this role exists to fix, across every brand AMZ Prep touches.





You find the problem, you size it, and you make sure it gets fixed and used. You are accountable for adoption.

What you'll do:
Brand Discovery and Process Audit

Run the deep dive audit that opens every recent brand engagement: systems, process, people, volume

Surface how work actually happens, which is never how the SOP says it happens

Sit with the brand owner in the morning and the operator on the floor in the afternoon, and stay credible in both rooms

Ask the questions that get the truth instead of the org chart answer

Roadmap and ROI Modeling

Put a dollar figure on what is broken: hours, margin leakage, errors, headcount avoided

Rank the bets by easiest win with the highest ROI impact

Deliver a roadmap the brand can actually act on, not a maturity model

Set the baseline metrics before anything ships so the impact is provable later

Hands-On Build With the Pod

Build alongside our engineering team; you are expected to be in the tooling yourself

Turn vague brand asks into technical direction the engineers can work from

Translate technical constraints back into plain language for the brand

Design and run short sprints that move decisions from quarters into weeks

Adoption and Change Management

Own the rollout past go live; shipping something nobody uses counts as not shipping

Train the brand’s team and develop the internal champion who owns it after we step backWatch usage, find out why it stalled, and fix the workflow or the training

Report measured impact back to the brand against the baseline you set

Account Health and Expansion

Own the relationship at the top; you are who the owner calls,



and who tells them the uncomfortable answer

Drive renewals by making the ROI visible and undeniable

Find the next workflow worth building inside the account

Turn what you learn in the field into the playbook the next brand starts from

What you'll need:

Strategy or Operations Background. 3 to 7 years across strategy, operations, product, or process design. Consulting, an AI-native company, an operations role in a real business, or you have founded something.

A Workflow You Personally Redesigned. Formally or informally. You can walk through end to end what you changed, why, and what happened.

Daily Hands-On Use of the Agentic Stack. Claude, ChatGPT, n8n or Zapier, Cursor, whatever is current. Building with them across multiple contexts, not reading about them.

Discovery Instincts. You know how to get to what is really happening on the floor.

Credibility Both Ways. You hold a room with an owner and hold a room with a warehouse operator, and neither one thinks you are a consultant.

Bias to Ship. You see three people doing something by hand and you have automated it before the next check in.

Travel. Willingness to travel to brand and fulfillment sites, particularly in the first weeks of a new account.

Background as Chief of Staff, ops lead, PM at an AI-forward company, management consultant (McKinsey Digital, BCG X, Bain Vector), service designer (IDEO, Fjord), or founder

Published writing, public speaking, or other public artifacts of your point of view on applied AI

Performance Metrics:

Account retention and renewal (primary KPI)

Adoption rate of shipped workflows at 30 and 90 days

Documented ROI delivered per brand

Time from kickoff to roadmap delivered

Expansion revenue within existing accounts

Playbooks and reusable assets contributed

Compensation:

Variable: Quarterly performance bonus tied to account outcomes, adoption, and retention. Target total cash meaningfully above base.

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📌 AI Strategist / Chief of Staff (Ontario)
🏢 AMZ Prep®
📍 Ontario

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