Technology Leadership Masterclass feat. Kelsey Ruger

March 1, 2024

Empower @ PROS presents Interface

In this episode, our hosts Jennifer, Matthew and Siara engage in insightful dialogue with Kelsey Ruger, the Chief Product and Technology Officer at Hello Alice. They dive into topics such as the synergy of being leading both product and technology teams, the value of investing in becoming a good leader, and the importance of learning how to operate in the business world while specializing in technology. The Heat Check segment introduces listeners to several conspiracy theories surrounding this year's Super Bowl game and a special Black History Month tribute to Doug Williams, the first black quarterback to play in and win a Super Bowl game.

Notable Quotes

“Yeah. I don't think people appreciate breaking things enough. Like when you break it and you have to fix it, you learn a lot. Even if your life is at risk at the moment, you learn a lot about how to get things working…”

“…start with making sure the vision is clear. So, if, for example, I want to do a new feature around AI, I'm not going to just go and say, we need this feature. I need to plug it into what our vision is. Like, what is our vision as a company, how this fits with what we said are the particular OKRs we're working on in that particular timeframe, and then make sure that the expectations are clear. Sometimes I will sketch out things or I'll give them an idea, especially if it's something really new that we haven't talked about before. What I do try to avoid is giving them the solution because that's why you hire people, right? Like you don't hire people as an executive to dictate to them, go build this thing that I thought of."

Chapters

00:00 Introduction and Guest Background
02:28 Kelsey's Journey into Technology
06:10 The Importance of Breaking Things and Learning
07:10 The Evolution of Technology and Its Accessibility
08:35 Transition to Chief Product and Technology Officer
10:18 The Role of a Manager and Leadership Skills
10:58 The Cognitive Load of Managing Multiple Teams
16:50 Advice for Aspiring Designers and Engineers
20:49 Building Diverse Teams and Hiring the Right People
23:14 Increasing Black Talent in Technology
27:14 Understanding Business Motivations
28:31 Personal Experiences in Corporate America
29:14 The Burden of Representation
30:29 The Heat Check Segment Begins
31:26 Super Bowl Conspiracy Theories
34:41 The College Admission Game
44:35 Black History Month Tribute
46:23 Wrapping Up and Guest Contact Info