Insights from Checkpoint On Using AI-Based Sales Training Roleplay

BY:  Rebecca Herson
October 7, 2021
Updated on March 18, 2024

Table of Contents

A Session with Check Point’s Sagy Kratu at SES Experience

According to Sagy Kratu, Head of Training and Product Positioning at Check Point, there are three main challenges in training salespeople:

  1. Getting the company’s messages out to sales employees. Sagy uses monthly “Cyber Monday” all-hands briefings, and weekly deep dive “boost” activities of 20-30 minutes targeted to specific sales roles.
  2. Standardization. A sales employee may have read a briefing or watched a video, but can they repeat the same messaging in a sales conversation?
  3. Verifying that once employees understand the messaging, they are consistently using it in live conversations.


Sagy, together with Second Nature’s CEO, Ariel Hitron, recently presented at the Sales Enablement Society Experience virtual conference about his experience using AI-based role sales training role play software to help overcome these challenges.

Check Point is a leader in cybersecurity solutions with over 60 different solutions and products, more than 100,000 customers worldwide, and an appropriately large sales team of around 2,000 sales people, channel partners, and security engineers (SEs). As you can expect, this creates a challenge in terms of rolling out new messaging, positioning, and/or products, and the challenge only deepened when COVID-19 forced everyone onto remote.

You can watch the full SES session here, or keep reading for a brief overview.

The Challenge: Getting Sellers to Practice, Managers to Listen to Recordings

In order to ensure salespeople were up to speed on key messages, Sagy described how they tried to encourage sales employees to practice their pitches, but also shared that it wasn’t working. The company was struggling to provide a safe place for sellers to practice without judgement, but with feedback. Sales teams weren’t interested in practicing more than once, max, plus managers didn’t have time to listen to recorded practice pitches and send feedback.

“These are major challenges: getting them to create the message, practice the message, and get feedback on the message to see how they deliver,” says Sagy.

The Impact of AI-based Role Play in Sales Training

That’s when Sagy discovered Second Nature and tried working with Jenny, our AI sales coach. All Check Point’s sales people and security engineers were invited to try an exercise or simulation with Jenny, and around 1,800 participated.

Sagy showed an expert example presentation that told the story of Check Point’s new cloud tools, and then left his employees to replicate it in their own way with Jenny. As Sagy notes “We’re a tech company, so our people are techies, they’re attracted to the edge of technology, the new things,” so there was a lot of excitement to be part of something so cutting edge.

On average, each of the 1,800 participants completed a practice session at least 3 times, when they’d normally have to be convinced to record a single session, and jumped from a median starting score of 60 to a final score of 80.

When asked for feedback, over 90% said they preferred to use an AI exercise like Jenny rather than a video exercise, an overwhelming vote for AI. “This is something that will take us one step ahead in our effort to provide more knowledge and, of course, the skillset,” said Sagy. “This is the main thing. You give them a skillset and a sandbox, a safe area where they can make tons of mistakes and correct them.”

Integrating AI Role Play into a Sales Training Cadence

Running a pilot sales training program isn’t the same as including something as part of your regular sales training cadence. Sagy has since been using Second Nature to roll out a new exercise every month, requesting sales people and sales engineers to complete the exercises as part of their weekly “boost.”

Sagy emphasizes that they use Second Nature’s AI sales role play as part of a unified sales training system. “I believe that each trainee or salesperson needs to have one system and we can’t send them different links, this system, that system, and so on.” Check Point’s Learning Management System is a one stop shop that includes Second Nature as part of the system.

Second Nature’s API automatically updates the LMS with data and it’s all integrated with the active directory, so each manager can enter the system to see a heat map showing their team and where they are with the different solutions.

“It’s an amazing tool because it provides the first line managers with the information they need on what to invest, where to invest, in terms of knowledge and skills,” comments Sagy.

AI for Remote Onboarding

COVID-19 also threw a monkey wrench into Check Point’s onboarding system. Ordinarily, inexperienced new hires would be brought to their headquarters in Israel for an extensive nine-week onboarding experience, and experienced sales talent for one week, but the pandemic made that impossible.

Check Point had to create a lot of e-learning content instead, but “we were fed up with tests.” Sagy also noted that just because a new hire can answer questions correctly, it doesn’t mean that they understand it properly or can turn it into an effective real time conversation.

That’s where AI-based role play came. With the addition of Jenny, Check Point had new hires consume information, participate in some live synchronous and asynchronous sessions, ask questions as much as they like, and then use Jenny for the final exam instead of a multiple-choice test.

“Down the line, we get better-prepared people after an onboarding process, and hopefully we’ll be able to cut short the onboarding process, which means we’ll have more viable salespeople faster in the field, and that in itself is worth millions,” said Sagy.

Moving Forward with AI Role Play

The story isn’t yet over of Check Point and its adoption of Second Nature’s AI-based sales training software. Currently, the company is only offering the software to Check Point sales employees, but much of their sales take place through channel partners, so Sagy and his team are discussing ways to leverage Jenny for their partner community to promote Check Point to their wider sales ecosystem.

Sagy also hopes to improve his ability to track KPIs that prove the impact of AI role play. Check Point has been using Second Nature for around eight months, so they are reaching the point where they can compare conversion rates, pipelines, and deal sizes between last year, without Second Nature, and this year. He hopes to see an increase on Check Point’s regular yearly growth.

Sales Training that Utilizes AI Role Play Offers Scale and Speed

Overall, Sagy emphasizes that Second Nature’s AI-based role play brings scale and speed to ongoing sales training and onboarding processes.

“It’s the scale and speed again,” he concludes, adding “For sales people, it’s a no brainer.”

Watch the full interview from the Sales Enablement Society Experience virtual conference.

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About the author

Rebecca Herson

Rebecca is head of marketing at Second Nature.

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