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The Nitty Gritty Of Sales Engagement with Ollie Whitfield

Published on June 27, 2022


In this episode of the Love Selling Hate Sales podcast, Joshua talks to Head of Growth Marketing for VanillaSoft, Ollie Whitfield. Ollie talks about the need for sellers today to stop using spam-based marketing techniques, and why intentionality is the name of the game when it comes to cold outbound email outreach.


  • How social selling hooked Ollie into sales engagement
  • Being a salesperson is a lot like being a CEO
  • What’s hot and what’s not with sales engagement in 2022
  • Personal Relevance vs Business Relevance 
  • Best practices for outbound cold email


Joshua: “People’s attention are at a premium and it’s our job as sellers to get creative really do your research, understand the person, connect with them at the human level and really start to break through that way, as opposed to these spam-based approaches.” 

Ollie: “You have to build relationships with people, you have to do the hard stuff, you have to be productive, you gotta organize your calendar, you’ve got targets, you know revenue, all of that stuff. If you’re good at sales you could probably be, in most cases or at least close to being a pretty decent founder.” 

Ollie: “In our market, for example, at Salesforce or at Hubspot, if they have this groundbreakingly new study or this new stat that I should know about based on what you know about me, my persona, my job, that’s a way to create some commonality. What people do all the time that’s wrong about this, they always recite some company I’ve never heard of and I could care less about and I don’t even know if it’s real. And then the stat is always something stupid like ‘Marketers are 79% more likely to achieve their goals if they do A.'”

Ollie: “It’s kinda like saying when you go bowling, do you use the rails? I don’t use the rails. I’m kind of like, no I don’t  do that I’m too cool for that. But writing with a framework is kind of the opposite of that. You should be proud of saying yeah, I do. I’m intentional about how I write my emails.” 

Connect with Ollie and his work in the links below:

About Josh Wagner: 

Josh is a growth advisor and the host of the Love Selling Hate Sales podcast. He specializes in helping executives understand modern marketing and sales to drive growth in a scalable way. 

To learn more about Josh and his work, follow the links below: