Sales Enablement, Demonstrated
The Sales Enablement and Proposal Specialist role at Data Society runs from prospecting to proposal. Rather than describe how I would do that work, I did it. This page walks through one complete run, on Walmart, built entirely from public information in a single working session.
Three days before this exercise, on October 14, 2026, Walmart and OpenAI announced an expanded partnership: Walmart is among the first partners embracing OpenAI Certifications, is rolling out ChatGPT Enterprise across its teams, and has committed roughly $1 billion to training through 2026. About 1.5 million US associates already use deployed AI tools. It is a Fortune 1000 account with an announced budget, a live trigger, and a named learning organization. It is also the honest hard case, because the obvious question is what an outside training provider adds when certification is already free. The work below answers that question the way the role would: research first, qualify honestly, then tailor everything to the answer.
Step 1
Public source research on the account: trigger events, announced investments, deployed tools, the buying center, and the capability gap an instructor led provider can fill. The brief ends with a recommended first move, because research that does not change the next action is decoration.
Read the research brief (PDF)Step 2
The account scored against a written rubric of six criteria, the same discipline I use in CRM across roughly 15,000 contacts. Walmart scores 29 of 30, Tier A, with the one held point explained. Named prospects are mapped by buying center role, each with an engagement angle and an honest verification note.
Read the prospect map (PDF)Step 3
Sales collateral written for this audience, not a generic capability sheet. It speaks to Walmart's learning team in their own public language, positions Data Society as the application layer on top of certification, and closes with a low risk pilot as the first step. Data Society capabilities are described from its public website.
Read the one pager (PDF)Step 4
A proposal draft for AI Fluency in Practice, an instructor led program for store and supply chain managers: executive summary, understanding of the need, program design, a 10 week delivery plan, scope and assumptions, and measurement. Pricing and cohort size are deliberately left open for scoping with the Data Society team, the way a real proposal specialist would leave them.
Read the proposal outline (PDF)Step 5
Every record logged the way the role requires: account, contacts, stages, activity history, next steps with owners, and a handoff note a salesperson can act on without asking a single follow up question.
Read the tracker view (PDF) Download the tracker (CSV)This page and its documents were prepared by Mike Dirks for the Data Society Sales Enablement and Proposal Specialist application. They are a demonstration of process, built from public information only. Mike is not affiliated with Walmart Inc. or Data Society, no contact has been made with Walmart, and nothing here has been sent to Walmart. Data Society capabilities are described from datasociety.com.