Behind the Purchase

Interview with Aaron Kenney VP of Revenue Operations at Dialpad

In partnership with

Welcome to Behind the Purchase!

If you’ve been reading The Seller’s Daydream, you’re used to sales lessons through stories set in ancient markets. This is going to be different.

In Behind the Purchase, we’re diving straight into the buyer’s world. Imagine sitting face-to-face with your customer, hearing firsthand about the real emotions, challenges, and decisions they face. We bring you insights directly from buyer interviews—revealing what truly drives their choices.

My goal? To help you create effortless buying experiences, build stronger relationships, and close more deals.

Let’s jump in!

What's to come!

Interview:

Click the link above to access a Notion page where you can easily view the questions and jump directly to their answers in the transcript with just one click.

Full Audio Recording

3 Learnings

1: Focus on the Admins, Not Just the Decision-Makers

Learning:
Contrary to the common approach that prioritizes engaging only the economic buyers and champions, Aaron points out that the admins or end-users — the ones who will actually use and manage the tool — are often overlooked but play a crucial role in the decision-making process. If these individuals are not bought into the product, it significantly increases the risk of the deal falling apart.

Question: "What can sellers do to best serve you during those post-demo conversations to make those valuable for you and your team?"

Quote: "It is kind of... I've never thought about that way to be honest with you after a lot of time of doing this. But yeah, that's a big-time deal breaker in there. Like, did you find that person who is actually gonna build this? And did you get them on board?"

"It is kind of a hidden decision maker... because if Shawn (admin) didn’t feel comfortable running it (software), I probably wouldn't have moved forward. Because who am I going to get to run this tool that everybody in the field is supposed to be using?"

2: "I'll Get Back to You" Creates Doubt

Learning: Contrary to the common belief that deferring an answer with "I'll get back to you" is a sign of thoroughness, Aaron reveals that it actually can diminishes trust and confidence.

Question: "Tell me about that. How do you feel when a seller says, 'let me get back to you on that?"

Quote: "I think you lose faith in a way, or lose confidence that you can do what you want to do with it.”

"You start asking those tricky questions, and there's not a good answer. I think that's the one for me, which is... you know, you're not prepped for, or you don't have a good way to answer them. That for me is when I start to lose faith of like, man, I just sat on an hour, Demo. I had like 10 questions that I asked, 8 of them didn't get answered."

3: Productivity Isn’t About Activity; It’s About Revenue Impact

Learning: Aaron's approach strips away these activity-based metrics and focuses solely on the output—closed bookings relative to headcount—aligning productivity directly with revenue impact rather than busyness or effort. This perspective implies that it doesn’t matter how much activity a rep does; what matters is the tangible financial result they produce. By focusing on the bottom-line impact, Aaron challenges the traditional view that values quantity of activity over the actual revenue outcomes.

Question: "How do you define sales rep productivity? Because you said productivity is one of the biggest levers."

Quote: "It's just annual bookings divided by productive headcount. So if you're on a ramp, whatever your head count was for that year, we don't count a ramped rep as one. It's, you know, whatever your percentage ramp was.

1 Idea to Apply Today

Use ChatGPT to analyze your call transcripts and pull out common questions and your answers, creating a Q&A bank.

Prompt

"I have a call transcript that I want to analyze to extract the most common and challenging questions that were asked during my conversations with prospects or clients. I want to create a Q&A bank that includes both the questions and my responses. Please analyze the following transcript and identify each question asked by the prospect or client and the corresponding answer I provided. Highlight questions that seem challenging or require detailed responses. Also, group similar questions together if possible. Here is the transcript: [insert call transcript]."

How the Prompt Works

  1. Transcript Analysis: The prompt instructs ChatGPT to review your call transcript and focus on identifying all the questions that prospects or clients ask during the conversation.

  2. Extracting Questions and Answers: It also directs ChatGPT to pull out the answers you provided for each question, helping you see how you handled the inquiry and what specific information you offered in response.

  3. Highlighting Challenging Questions: The prompt requests ChatGPT to flag the challenging questions that required detailed responses or might have been difficult to answer in the moment. This step helps you prioritize which questions need more preparation.

  4. Grouping Similar Questions: ChatGPT is asked to group similar questions together, allowing you to identify patterns or recurring themes in the questions that you can address with a standardized response.

  5. Creating the Q&A Bank: Once ChatGPT extracts and organizes the questions and answers, you'll be able to compile a Q&A bank that you can use to study, refine your answers, and prepare more thoroughly for future conversations.

Step-by-Step Guide to Apply the Prompt

  1. Gather Your Call Transcripts: Collect your call transcripts for the past year and organize them in a digital format (like a Word document or PDF) so that they are ready to be inputted into ChatGPT.

  2. Chunk the Transcripts: If your transcripts are lengthy, break them into smaller chunks, as ChatGPT has a limit on how much text it can process at once. Aim to keep each chunk within 3,000-4,000 words to ensure ChatGPT can handle it.

  3. Input the Transcript into the Prompt: Copy a chunk of your transcript and paste it into the prompt where it says "[insert call transcript]." If you have multiple transcripts, you will need to repeat this process for each one.

  4. Review the Extracted Q&A: ChatGPT will extract questions and answers from the transcript. Carefully review the output, paying special attention to the challenging questions and the quality of your responses.

  5. Organize and Standardize: Create a spreadsheet or document where you can organize the extracted Q&A pairs. Group similar questions together and refine your answers to create a standardized response that you can use in future conversations.

  6. Update Regularly: As you continue to have more calls, update your Q&A bank with new questions and answers. Over time, this will help you create a comprehensive resource that you can use to prepare for a variety of scenarios.

Shape the Next Interview

If you could ask your prospects any questions what would you ask?

Submit questions here.

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https://www.thesellersdaydream.com/p/behind-the-purchase

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