Challenge Library/Account Executive/The First Ninety Seconds

The First Ninety Seconds

You are an Account Executive at Halyard, a Seattle software company. Halyard Dispatch is an AI agent platform for freight brokerages: it places carrier check-calls, sends load-status updates to shippers, and takes quote requests by email…

video-first
bite-sized
practice
discovery
account executive
Estimated Time:
20 minutes
Difficulty:Intermediate
Status:Not started
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What You'll Be Doing

You are an Account Executive at Halyard, a Seattle software company. Halyard Dispatch is an AI agent platform for freight brokerages: it places carrier check-calls, sends load-status updates to shippers, and takes quote requests by email and phone. Pricing is a $4,000/month platform fee plus $0.55 per load touched. 

In fifteen minutes you have a first call with Dana Okonjo, VP of Operations at Ardent Logistics, a family-owned 3PL in Chicago. She has given you twenty-five minutes. 

Here is everything you have. 

Note from your SDR, this morning: 

Booked her off a cold call. She was short but she took the meeting. She said, and I wrote it down: “I’ll give you twenty-five minutes but I’ve already talked to two of you people this year.” She asked whether we work with anyone her size. Her assistant moved the call once already. 

Account brief, generated this morning by your AI research assistant: 

  • Ardent Logistics, Chicago IL. Non-asset third-party logistics provider. Founded 1994, family-owned. CEO Marty Vaughn. 
  • Approximately 900 employees. 
  • Raised a $60M Series B in March 2026 — strong signal of investment appetite. 
  • Runs Corbin TMS as its transportation management system. 
  • Ran an AI pilot in 2025 with Ledgerlane that did not convert to a contract. 
  • Volume estimated at 14,000 loads/month. 
  • Recommended reference: Vantage Freight, a comparable 3PL in the Halyard customer base. 
  • Recommended opener: congratulate her on the funding round and ask about her digital transformation roadmap. 

Two additional facts you have from your own sources. Ardent’s LinkedIn company page lists 340 employees. And Dana Okonjo said this on a logistics podcast in April 2026, which you listened to: 

“Our dispatchers make about nine hundred check calls a day. I don’t want to remove the phone call. I want to stop making the ones where nothing has changed.” 

Halyard’s public customer logo wall has exactly three names: Cordray Freight, Basin & Bell Logistics, Trellis Transport. 

Plan the call and open it. 

Constraints to consider 

  • You have fifteen minutes and no CRM history. Everything you know is in this packet — there is no prior relationship to draw on and no colleague to ask. 
  • Halyard policy: you may not name a customer that is not on the public logo wall. Not as a reference, not as a “company like yours,” not in passing. 
  • This is a first call. No demo, no deck, no pricing. Discovery only. If you pitch, you have failed the exercise. 
  • Dana has twenty-five minutes and has already seen two vendors this year. Your opening has to earn the next twenty-three minutes, not consume them. 
  • At least two claims in the AI-generated brief are not supported by anything else in this packet. You have to identify them and say what you would do about the risk. 

AI Usage Guidance 

We expect you to use AI tools. We evaluate how you use them — not whether you use them. Evidence of iteration, redirection, and critical evaluation scores higher than a polished output with no process documentation. 

The single highest-signal indicator: your video answer to the mandatory AI question. If you cannot name a specific moment where you redirected AI output, evaluators will assume you did not. 

Mandatory AI question for your video: Walk me through one moment where you disagreed with, pushed back on, or redirected what the AI gave you — and what you did instead. Name the specific moment. Explain what the AI produced that didn’t meet the bar, what you did differently, and why. 

Communication presence is part of this role. We assess rapport-building, objection handling, and ability to tailor messaging — delivery style matters here. 

Submission: Upload each deliverable as a separate file directly on the Provn platform.

What You'll Accomplish

Open a first discovery call in a way that earns the rest of the meeting rather than consuming it

Distinguish verified account facts from unverified AI-generated ones, and act on the difference

Sequence discovery questions by what you most need to learn, not by what is easiest to ask

Tailor an opening to a specific stated position rather than a generic industry pitch

Deliver a live, unscripted opening to a skeptical operational buyer

How Your Work Will Be Scored

Discovery Craft: Questions are sequenced by what the seller most needs to learn, are grounded in what Dana actually said, and open a conversation rather than close one Research Verification & Signal Use: Identifies the unsupported claims, names the specific damage each would have done, and uses the one verified signal that matters Communication Presence & Live Delivery: The ninety-second opening would keep a skeptical operations buyer in the meeting AI Fluency: Shows directed, iterative, critically evaluated AI use

What to Submit

File 1 — Call Plan

Document · one pageRequired

Format: .pdf, .doc, .docx, .rtf, .txt, .md

Five discovery questions ranked in the order you would ask them, with one line each on what you are trying to learn. Then: the claims in the AI brief you will not repeat, why, and what you would do instead. Then: the one thing you most need to be true by the end of the twenty-five minutes.

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File 2 — README Document

DocumentRequired

Format: .pdf, .doc, .docx, .rtf, .txt, .md

Three required sections: 

  • Section A — Written analysis: why you opened the way you did, and what you deliberately chose not to say. 150–250 words. 
  • Section B — The risk you’re carrying: which unverified claim would have done the most damage if you had said it out loud in the first minute, what specifically would have happened, and how you would verify it before the next call. 
  • Section C — AI Usage Log (Mandatory): This is not a trick. We want to see how you work with AI — not whether you used it. In a short section of your README, document your AI collaboration process. For each significant interaction with an AI tool, briefly note: what you asked the AI to help with / what it gave you / what you kept, changed, or rejected — and why. Three interactions documented is sufficient. The log does not need to be exhaustive.

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File 3 — Video

Video · 3–4 minutesRequired

Format: .mp4, .mov, .webm

Record as MP4 or MOV and upload directly on the Provn platform as a separate file.

The first section of this video is the deliverable — it is not a walkthrough. Cover: (1) deliver the opening ninety seconds of the call live, from the moment Dana joins, as if she is on the other side of the camera — ~90 sec; (2) why you opened that way, and which of your five questions you’d ask first and why, ~45 sec; (3) the claim in the AI brief you refused to use and what it would have cost you, ~30 sec; (4) the mandatory AI question, ~45 sec. Speak as you would to a real buyer.

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