Sales Development sits at the intersection of Marketing, Sales, Ops, Product, and Executives… and the natural result will be Sales Development Leaders bringing those together in their career to become Chief Sales Development Officers and eventually, Chief Revenue Officers. 

But what is the process of becoming a CRO? What do you actually have to do to be successful?

OUR guest this week is going through that process now, and breaks down his process specially, the good, the bad and the ugly. 

This is critical listening to all the strivers out there who want to leverage their career to new heights!

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Notable Quotes:

“It needs to be safe. They need to say they can disagree with you.” – Darryl Praill on kicking VanillaSoft’s CEO out of the company’s communication channels

“I’m just executing what other people have already done.” – Darryl Praill

Brief Summary

Darryl Praill is Canada’s leading B2B marketer, and today he’s VanillaSoft’s Chief Revenue Officer. In this episode, David welcomes Darryl as a return guest and together they break down what it means to be a modern CRO.

Today’s Guest: Darryl Praill

Darryl Praill is the CRO of VanillaSoft, a software that helps sales development representatives streamline processes and generate more revenue. He made his way through the ranks from CMO to CRO and now he’s enjoying his own yacht. In this episode, David talks with Darryl about the opportunities and challenges he has faced since becoming VanillaSoft’s CRO.


The episode touches on the following key topics and ideas:


  • Darryl shares his past roles that led him to being VanillaSoft’s CRO today (02:36)
  • How has the CRO role changed over the last decade? David and Darryl dives deeper into the responsibilities of CROs today (03:13)
  • Darryl narrates the moment when he was offered the role of CRO and the main responsibility that came along with it (05:07)
  • Where do sales and marketing intersect and where do things get blurry? Darryl shares his personal experience on distinguishing between the two (05:48)
  • Darryl divulges what he did upon learning that he was going to be a CRO (07:57)
  • The 90-day CRO plan that Darryl is following (09:22)
  • The questions that Darryl asked his newly-acquired Sales team during his first days as CRO and the problems that arose from the answers he got (09:45)
  • Sitting in sales calls and pinpointing the main challenges of the team (13:16)
  • How Darryl figured out that regular product and skills training was the simple yet transformative solution to their current sales challenges (14:50)
  • Restructuring SDRs to manage inbound and RAEs to conduct outbound, account-based approach (15:31)
  • Implementing ABM for a more focused sales model (15:49)
  • Darryl shares the idea behind VanillaSoft’s Book Club and how Book Club helps in sales training (17:40)
  • The importance of encouraging your team to communicate constantly especially during WFH arrangements (19:04)
  • Building two differently-focused teams, Sales Enablement and Revenue Operations, to translate Darryl’s CRO plants into actual revenue (20:10)
  • What is the biggest skill that a CRO needs to have? Darryl shares his answer based on his learnings on the job (23:04)
  • Why it is vital to communicate plans and expectations when restructuring a sales model (23:35)
  • How Darryl is preparing for pipeline reviews with concepts he came up with months ago (25:32)
  • Sifting through and reviewing content with transcription and captions to ‘mine gold’ and to train sales representatives (27:28)
  • Closing statements (30:08)

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