Hunters + Unicorns: The 33 CxOs – Scott Sinatra #013

I think it’s really important when you’re leading or building a sales organization to pay attention to the nuances of the sale and modify the playbook to meet the growth strategy of the business. There is no cookie cutter. There are no shortcuts. There are elements that stay static, but adapting with agility has helped me contribute to building and growing these companies.”  Scott Sinatra 

Hunters and Unicorns shares the playbooks from leaders, founders, executives and investors from high growth technology companies.  

In this special edition series The 33 CXOs we investigate the greatest success story in the history of software sales. Discover how thirty-three sales execs from one organisation, BladeLogic, became CXOs in the world’s 100 fastest growing technology companies. We uncover the stories and playbooks of the most prolific sales leaders in the industry. 

Episode 11 features Scott Sinatra, an accomplished CRO, investor, advisor and mentor with over 20 years of experience leading and building word-class enterprise software sales teams.   

Scott’s SaaS career began at PTC in the 1990s. After reading an article in Forbes Magazine about their “elite team of sales athletes capturing the market,” he was instantly attracted to this challenging industry and the opportunity to be surrounded by a next level sales force that he could learn from. He took a job as an Individual Contributor so that he could learn the ropes and master the science of selling and since then, his career has taken an upward trajectory. He went on to hold senior sales leadership positions at Bladelogic (IPO 2007) and BMC Software (acquired Bladelogic 2008). He also served as Senior Vice President of Worldwide Sales at Glassdoor and was, until very recently, leading global expansion at Glint as Vice President of EMEA.  

I’ve been managing teams since I was 28 but what I didn’t know going into PTC was how to sell software. It wouldn’t have been appropriate to put me in a management position at PTC right away, and I was fine with that. Let me go and learn some new skills, let me learn what software is all about, and then potentially from there, I move up and through the organization. That was my mindset, and it was absolutely the right thing for them to do, and the perfect thing for me to go through at that time. 

With a determination to learn and grow, Scott mastered the playbook at PTC. He rolled up his sleeves and “got dirty” doing deals in order to acquire the vital knowledge and “scar tissue” he needed to succeed in the software sales industry. He witnessed first-hand how the implementation of methodologies, coupled with the right team of people could turn a stagnant company into a growth engine and he used his experiences to further progress in his career and form a unique leadership style of his own. 

You can’t just take a playbook and plop it into a situation without adjustment. You have to be able to use it to the benefit of making strong decisions about people, growth strategies and targets. I was able to implement the playbook, with tweaks, to grow fast and consistent at both Glassdoor ($1M to $20M in 18 months, eventual exit) and Glint ($0 to exit in less than 5 years). Those outcomes had everything to do with execution and the playbook was the foundation.” 

In this vodcast you will discover: 

  • How to use MEDDIC as a compass 
  • The importance of creating actionable feedback  
  • How to use “the walkaway” strategy to test whether you have a champion 
  • Why it is important to adapt and change to new situations 

Scott’s unique insight and experiences in this industry have enabled him to build teams of exceptional skill and achievement. He believes that building companies is a team sport and is passionate about culture, asking questions and gaining feedback to find out what is driving his people. Scott’s playbook is a reflection of his ability to adapt to the everchanging landscape of tech and his dedication to the wellbeing of his teammates.  

We discuss Scott’s incredible career journey from IC to VP and find out what he thinks it takes for a company to reach unicorn status. This wide-ranging discussion is essential listening for those with an interest in sales strategy, as well as anyone with a passion for the technology space. 


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