Creating a Revenue Team Through Pragmatic Alignments of Sales, Marketing, and Customer Success: Darryl Praill, CRO at

Darryl Praill CRO VanillaSoft Episode Marketing and Sales Alignment Revenue Quote

Episode Summary

In today’s episode, we have a very special guest Darryl Praill who is currently the CRO of VanillaSoft a SaaS leader in enterprise-ready Sales Engagement software.

He’s a seasoned executive software professional, having navigated in his 30 plus year career through senior leadership roles in sales, marketing, and most currently leading the revenue team at VanillaSoft.

He has earned and been awarded the following credentials and honors, voted by the industry and his peers:

2020 Top 10 SaaS Branding Expert ★ Top 19 B2B Marketer To Follow ★ Sales World Top 50 Keynote Speaker ★ Host of the Inside Inside Sales Podcast

He’s helped raise millions in funding and taken companies public. He’s held executive roles with companies like SAP (Sybase), IBM (Cognos). He sought out by industry leaders including AC Nielsen,, UBM, and Tweed

We deep dive into his learned business acumen and experience as a former VP of Sales, recent CMO at, and how he has managed to successfully, with some bumps along the way transitioned into his new CRO (Chief Revenue Officer) role at VanillaSoft.

You’ll get a lot of his proven sales and marketing strategies and leadership insights from the very opinionated, informative, and always entertaining Darryl Praill.

Show Notes & Bio

Darryl shares some of his must-do strategies to build better alignment between sales and marketing to create the revenue engine.

He believes firmly in SLA, sales lead agreements to keep both teams focused on revenue and maintain transparency between marketing and sales goals.

We discuss marketing attribution to sales pipelines and what metrics are important to a CRO.

Darryl shares some lessons learned on the people process of managing a revenue team and how to avoid misunderstanding and negative outcomes with your sales teams.

He explains the criticalness of breaking down silos between marketing and sales, both in process, people and to build a culture of revenue team first, department or divisions second approach.

We discuss some of the mar-tech that he deploys at VanillaSoft to rev up his demand-gen engine and how reverse engineering revenue goals to SQLs is key to putting a strategic demand gen plan for successful revenue attainment.

As always, Darry doesn’t hold back, he injects a bit of his humor but is all business about the practical and pragmatic approaches to build a world-class revenue team at VanillaSoft.

He also gives us some of his favorite marketing/sales book recommendations such as Blue Ocean and some insights on what advice he would have given a younger Darryl Praill.

Darryl Praill CRO VanillaSoft Episode Marketing and Sales Alignment Revenue Quote

The five key CRO take-aways he covers in more detail during the full podcast:

  1. CRO’s #1 Job is to create a revenue-centric team
  2. Focus on people, process, and then mar-tech
  3. Lead one revenue meeting not siloed department meetings
  4. Always drive-up conversations to C-Suite
  5. Create SLAs and Comp Plan Alignment

Bio and Contact information: Darryl Praill

CRO @ VanillaSoft ★ 2020 Top 10 SaaS Branding Expert ★ Top 19 B2B Marketer To Follow ★ Sales World Top 50 Keynote Speaker ★ Podcaster

To learn more about his bio and current role, he can be reached to connect on LinkedIn

Twitter Profile: @ohpinion8ted

Darryl’s Book Recommendation:

Crossing the Chasm, 3rd Edition: Marketing and Selling Disruptive Products to Mainstream Customers

Blue Ocean Strategy, Expanded Edition: How to Create Uncontested Market Space and Make the Competition Irrelevant

Gap Selling: Getting the Customer to Yes: How Problem-Centric Selling Increases Sales by Changing Everything You Know About Relationships, Overcoming Objections, Closing, and Price

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Smart Chickens is intentionally a quirky, yet intelligently poised dialogue B2B SaaS and Demand Gen podcast. In this podcast, you will hear from professionals in SaaS and B2B share best practices they deploy at their organizations as well as a bit about their career journey stories. They also will share their point of view around creativity, innovation, and strategies they’ve used to become better at marketing, sales, and leadership roles to help drive revenue and market share.

We highlight both the wins and losses, what strategies worked, and how their “different way of thinking” made them, their teams, and overall their companies better.

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