Behind the Scenes of a Successful Deal Desk

Tips for Staying Motivated and Achieving Results with OutSystems

Cockpit Counsel

Behind the Scenes of a Successful Deal Desk



In this episode of Cockpit Counsel, Tim Parilla sits down with Shawn Hoyt, Vice President, Commercial within the legal team at OutSystems. Shawn brings a wealth of experience from various roles and dives deep into the secrets of building and managing a successful deal desk. He also shares invaluable tips on staying motivated in every aspect of life, both personally and professionally. Tune in for an inspiring conversation filled with wisdom! 

Key takeaways

  • The importance of expressing curiosity in the business 
  • Transforming how the deal desk operates as the business grows 
  • Challenges and opportunities that come with leading non-legal teams 
  • And more!


  • 00:48 What is your preflight ritual?
  • 02:12 Tell us a bit about your career path
  • 05:38 When you started at OutSystems, what was the customer and employee base?
  • 08:06 How have you changed the way the deal desk operates as the business has scaled?
  • 11:45 How do you approach different deal thresholds?
  • 13:09 What was the most difficult adjustment to managing a team of non-lawyers for the first time?
  • 16:47 What was your biggest challenge as a COO?
  • 24:12 Let’s talk about your fitness journey. 
  • 26:45 What drew you to Spartan racing?
  • 32:52 What is your number one tip for maintaining motivation, personally and professionally?
  • 34:31 How does your mindset help you lead and develop your team professionally?
  • 37:41 What is your hot take about working in-house?


Tim Parilla Headshot
Tim ParillaChief Legal Officer, LinkSquares
Shawn Hoyt headshot
Shawn HoytVP, Commercial, OutSystems

The sky’s the limit. Hey, why not get a demo?