Case Study

From Transcripts to Trust: How AI Helps Us Win Deals with Heavily Personalized Proposals

The Vision

At DataCose, we believe that tech should enable and empower businesses, not hold them back. But selling tech transformation requires more than just explaining features, it requires empathy and being able to communicate how the solution helps the business owner you’re speaking with.

In one project, we faced a tough challenge:

Two key decision-makers.
Very different personalities.

One led with emotion and people.
One led with logic and data.

We only had one shot to earn both of their trust. We needed a way to speak to both of them at the same time, without losing either one.

The Challenge

This wasn’t your typical sales presentation.
We were deep in discussions with a company where:


- The Head of the business cared about logic, numbers, and measurable value
- The Heart cared about people, security, and the team’s lived experience

They didn’t always see things the same way.
And we knew that a generic pitch wouldn’t work.

We had hundreds of pages of call transcripts from early conversations spanning weeks. We knew it was a goldmine but it was too much to comb through by hand in time.

We needed a fast, smart way to analyze what mattered most and craft a compelling message that would land with both owner

The Turning Point

We turned to AI for help. Using AI to Craft a Dual-Persona Sales Plan

Loaded 100+ Pages of Call Transcripts

We gave the AI 100+ pages of raw call transcripts messy, unstructured, real-world conversations.

Assigned AI a Role: Communication Expert

We asked the AI to act as a personality expert, breaking down how each stakeholder communicates and what they care about.

Got a Clear People Map

The AI gave us something powerful, a people map:

- Co-Founder A was the Heart of the company: team-focused, mission-driven, rooted in people and security.
- Co-Founder B was the Head: data-driven, long-term thinker, focused on logic and efficiency.

Co-Created a Message That Landed for Both

Then we asked AI to help us design a sales plan that spoke to both personalities.It gave us a core message:

“Empowering your mission through efficiency.”

Then, it broke down how to position each milestone:

For the Heart: how it helps the team feel supported
For the Head: how it improves metrics and solves problems at scale

The Transformation

In less than an hour, we had:

A sales strategy tailored to real people

Messaging that aligned both values and outcomes

A presentation outline that ultimately landed us the deal

What usually takes hours of analysis and research, we had a proposal that effectively communicated the value of the project to both stakeholders.We didn’t just make a pitch.


We ensured our clients understood that the tech plan tied directly to their personal goals

Why This Matters

AI helped us communicate effectively to the people we’re trying to serve.

It saved time.

It surfaced insights we may have missed.

And it helped us build trust faster.

This is what we mean when we say AI isn’t just about automation.It’s about elevation, thinking better, connecting faster, and showing up smarter. It’s for amplification.

The Transformation

Coastline Boat Lift Covers didn’t just digitize, they leveled up. Here’s what changed:

More Leads, Less Work

The team now handles more inquiries than ever without adding headcount. They can quote, measure, and close deals remotely, no more bouncing between tools or waiting to “get back to the office.”

Paperwork Monster Gone

Previously, information had to be manually transferred between paper notes, spreadsheets, and emails, introducing delays and frequent errors. By automating these steps, we eliminated critical bottlenecks. Data now flows seamlessly from one stage of the process to the next, dramatically reducing turnaround times and enhancing internal collaboration.

Smarter Decisions, Happier Customers

From the shop floor to the office, everyone knows what’s happening. Leaders get real-time visibility. The team feels in control. And customers feel it, too.

Want to Sell Smarter and More Human?

We’re not just using AI to move faster. We’re using it to optimize strategy, sales, and communication.

If your sales team is trying to win complex deals with simple tools, we can help.

Let’s explore how AI can help you sell like a human at scale.

Check out our video testimonial with
Michael Jade, Founder of Renaissance Club

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