Episode TwoHundredFiftyNine

Don’t Assume Nothing: Sales Enablement Insights

Guest: Jonathan Ashkenazi, Head of International Sales Development at Guardicore

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About This Episode

Yes, they picked up the phone. But that doesn’t mean they actually want to talk to you — or that they have time right now.

Make this your motto: Don’t assume nothing.

Recently on Sales Engagement, I had the chance to speak with Jonathan Ashkenazi, Head of International Sales Development at Guardicore, about “Don’t assume nothing.”

Jonathan started his sales career at age 13 selling books door-to-door and most recently showed explosive growth by bringing his sales team from 2 to 7 in under a year. 

“That’s something that I really love in sales development, because it’s human development as well. It’s not just about the sales development,” he said.

Let’s dive into the conversation!

Conscious selling

Jonathan uses a method called Conscious Selling, which he described as the Sandler technique taken to the human level, credited to GuruGanesha.

This has helped him overcome the internalized stigma of selling with — let’s be honest — sleaziness. Instead, he learned about the triangle of fit.

  1. Technical fit. Can you even solve this technical problem before you go ahead?
  2. Business fit. Can they even pay for your solution?
  3. Personal fit. How do they feel about buying from you?

“In my life, I avoided or tried to avoid my best to buy from people I don’t like. I did not want them to make the money because they did not treat me with the right respect as a buyer,” he said.

When the triangle of fit is the right size, that’s a winning moment.

Don’t assume nothing

People tend to overlook the personal fit to their detriment. “Be conscious of the person you speak with. Be aware of their time. Don’t assume nothing,” Jonathan said.

Don’t assume nothing is one of the trademarks of conscious selling.

  • Don’t assume they need your product even if the webpage says so.
  • Don’t assume they want a demo even if you get a request.
  • Don’t assume they think they need you even if they’re reaching out with interest.


“By going with the notion and respect for him that you did not assume, even if I did my research, I can show the difference between assumptions and leading questions,” he said.

Here’s the crux of conscious selling and not assuming: Be conscious of who you are. Be conscious of the fact that you’re talking to other humans.

Pro tip: One of the best sentences that people don’t use on the phone is “I don’t know.” This gives you a chance to be human, be vulnerable, and move together on a journey of learning.

Dos and don’ts of cold calling

Here’s something you shouldn’t do:

“Don’t assume that I care about your product in any way,” Jonathan said.

When Jonathan himself takes a call and explains that it’s not a good time, and the other rep keeps talking…he’s just burned his vendor. If someone says it’s not a good time, the only answer is, “Sorry to disturb you, when would be a better time to talk?”

(Remember personal fit? Yeah.)

“You will be shocked how many of them will tell you when would be a good time to call. You put 10 minutes in their calendar, you’ve got a proper call setting,” he pointed out.

And here’s something you should do:

Connect the first line of a cold email to someone or something the recipient likes.

Jonathan read a cold email because it opened with a quote from Trish Bertuzzi, the author of a book he really esteems (The Sales Development Playbook). He even took a demo even though he wasn’t in the market.

Similarly, Jonathan connected with someone on LinkedIn because she was the only person to send a voice note, and that was intriguing because it was different.

<“They can take my knowledge as a top SDR in the past and be better than what I ever was. Why? Because they build upon my knowledge.” — Jonathan Ashkenazi>

Changes in the sales engagement space

Jonathan was in sales for many years before there was any sales enablement tool. He worked chiefly with Salesforce and Excel.

As an individual contributor, honestly, he didn’t like being told to use a sales enablement tool, but as a manager, he built the cadences and sequences the way that he thought they should be done.

“Be social, be nice,” he said. “That’s why it worked better for me rather than what I was told before. It helped my team tremendously.”

Build the templates… 

“I would build for all of them. I would let them basically do their job from a person who knows the job.”

…then let them keep building. 

“They can take my knowledge as a top SDR in the past and be better than what I ever was. Why? Because they build upon my knowledge.”

That’s what Jonathan loves about sales enablement tools, that it enables SDRs to avoid starting from scratch in creating their own cadences. They can build on the knowledge and methods that are already proven.

“Each and every one of my team members, basically I told them the same sentence: You will be better than I am,” Jonathan said. (You really have to listen to our conversation to hear how happy and proud Jonathan sounds about this.)

He hires curious, eager, smiley people. “You come to Guardicore with a smile, you leave with a smile, and I hope you will not leave anytime soon,” he said.

Jonathan’s parting wisdom

Jonathan: Don’t assume nothing. Really go with that. When you talk to a prospect, what’s in it for him? Don’t assume that he needs you just because you think he needs you. Listen to him, be conscious of what he’s saying. And be yourself. 

Connect with Jonathan on LinkedIn (and if he’s hiring, his profile will say so).

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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