From Pain Point to On Point: Transforming Sales Challenges into Wins

What does it actually look like when AI works with your sales team instead of against them? In this episode, Britt sits down with Royce Mason, a California native turned Oslo resident and sales enablement expert at Umbrella, to dig into one of the most pressing questions in modern sales: how do you integrate AI in a way that your team will actually use?

Royce brings a refreshingly grounded perspective to AI adoption, one that starts not with technology, but with people. Drawing on his background in finance, leasing, and enterprise sales, he walks us through how AI is reshaping the way reps train, prospect, and show up for their customers, and why forcing it from the top down is almost always the fastest way to kill adoption.

In this episode, we cover:
  • Why AI adoption breaks down at every level of an organization, and how to fix it
  • The power of AI-driven role play in reducing sales anxiety and building rep confidence
  • How one sales team improved their close ratio by 30%, increased deal size by 40%, and flipped their talk-to-listen ratio from 60/40 to 20/80
  • What a "future-ready" sales team actually looks like on a normal Tuesday afternoon
  • Why the best salespeople use AI to find 15 sure-thing prospects instead of dialing 1,000 long shots
  • The Iron Man analogy that perfectly captures the human + AI relationship in sales
  • Why sales will always be a trust-based, human-centered profession, no matter how advanced AI gets
About Royce Mason: Royce Mason is a sales enablement and growth expert currently based in Oslo, Norway. Originally from Woodland Hills, California, Royce has built his career across finance, leasing, and tech sales before finding his passion at the intersection of people, process, and AI. He now works at Umbrella, helping organizations build future-ready sales teams that use AI not as a replacement for human connection, but as a tool to deepen it.

Creators and Guests

Host
Brittney Moseley
Go-To-Market Director
Producer
Ellen Young
Marketing Campaign Manager

What is From Pain Point to On Point: Transforming Sales Challenges into Wins?

'From Pain Point to On Point: Transforming Sales Challenges into Wins with Gamification' is the podcast where we dive deep into the common challenges sales managers face and explore innovative gamification solutions to overcome them. Hosted by SalesScreen’s Go-to-Market Director Brittney, every two weeks, we'll bring you expert insights, real-world stories, and actionable tips to help you turn your sales pain points into on-point victories.