Case Study


How Windsor Scaled Sales and Closed High-Value Deals with Activated Scale

4X increase

Average Deal Size


What they do

AI-powered, personalized videos

Windsor, backed by Y Combinator, is a startup founded by two engineers with limited sales experience. The founders, Pranay and Andrew, were struggling to close deals and maximize their revenues. Their initial attempts to sell their services resulted in lower prices than they desired. They needed a sales expert to help them improve their conversion rates and negotiate better deals.

We sat down with Pranay Prakash, Co-Founder and CEO at Windsor, to understand how Activated Scale helped them to reach and close deals faster than ever before.

“We started looking through our network... but here was Nathan. He wanted to get involved in the startup space and wanted to help out so it was perfect because that is the kind of person that we would have spent a lot of time looking for.”

The Problem

There were 3 main challenges that the founders faced:

1. Limited Sales Experience of the Founders: Most startups are built by Technical teams who struggle to build sales momentum. As Technical founders, coding a great product comes easy, but selling it is difficult

2. Struggling to find the right sales talent through platforms like Upwork and Fiverr: Marketplaces such as Upwork and Fiverr are fantastic for roles that aren't sales related. Most freelance platforms don't vet their talent for skill putting the hiring risk on the customer.

3. Difficulty in committing to a full-time hire without proper evaluation: A good enough salesperson can interview well. But, the real results show up in a few months. By when a company has spent a lot of time and a lot of money. If the salesperson is unsuccessful, then all this time and money has gone to waste.

While there are countless clever ways to hire sales people, Windsor identified Activated Scale as the best way to hire vetted and experienced sales talent they can try before they commit full-time.

“We love this model of having somebody do a work trial with us. And that's exactly what Activated Scale gave us is the ability to have a contract to hire with somebody. You've already found the right people.”

The Solution

Hiring salespeople is tough and Windsor got the flexibility and experience they needed to build and execute their go-to-market. Windsor hired 2 experienced sales professionals through the Activated Scale platform. One of whom after a 3 month contract was hired as their Head of Growth.

Nate is an experienced sales professional with over a decade spent in building and scaling startups and scale ups.

“With Nate, we were not only reaching deals we couldn't have before, we were closing them at a faster rate than ever before”

The Results

After hiring Nate through Activated Scale, Windsor observed the following improvements:

  1. Significant increase in deal size: Nate was able to close deals at $2 to $2.50 per video, compared to the previous range of 85 cents to $1 per video. This represented a 4x increase in average deal size.
  2. Faster sales growth: Nate's prior sales experience allowed him to plug the gaps in the sales process, build their outbound motion, iterate their messaging and close deals.
  3. Smooth hiring process: Activated Scale provided a seamless and efficient way for Windsor to find the right sales talent without the risk of a full-time commitment. It took just 8 days from an initial call with an Activated Scale onboarding specialist to having Nate start!
  4. Greater flexibility: The contract hiring model provided by Activated Scale allowed Windsor to assess Nate's skills and suitability before offering him a full-time position.

“He was just really good at what he did. Closing deals that were very favorable for us... he increased our average deal size by Four X”

The Future

Activated Scale played a crucial role in helping Windsor scale their sales and close high-value deals. By connecting them with experienced sales talent like Nate, Activated Scale helped Windsor achieve greater success in their business. The flexible contract hiring model provided by Activated Scale made it easier and more affordable for startups like Windsor to access top-tier sales professionals, ultimately ensuring a strong return on investment.

“Activated Scale has fundamentally changed the trajectory for Windsor.”
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