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Roy Osing

Former President and CMO who scaled a startup data company to $1B in annual revenue; author, entrepreneur, and business advisor with 40+ years of leadership experience.

Aug 24, 2026

9:15
So what single piece of advice, and I know that's difficult, Roy, what single piece of advice can you give a business leader wanting to step out and do things differently?
9:25
Yeah.
9:25
And just before I, I get into that, Ian, I just wanna hit on a couple of, um, of, of points around actually not just overcoming the challenges, but actually getting people to accept the moves that we're trying to make because there's two things that were really, really important here.
9:43
One we kind of touched on, which is all about performance.
9:46
There's nothing more effective, okay, than getting people to accept change than when they see the results of that change in front of their very eyes.
9:56
And in this particular case, it was, it was top-line revenue performance.
10:01
So, uh, m- I personally, um, focused on making sure that that revenue line was going the right way, and not just talking about the need for change, but showing that it worked.
13:59
Yeah
6:32
What were some of the most important decisions that made that growth possible?
6:37
Yeah, and this is really going to be simple stuff, and people are going to scratch their head and say, what? Did that stuff really work? But let me just give you – there wasn't one thing, okay, Henry? There never is.
6:48
Success is not a function of one thing.
6:52
It's a function of many things working in harmony.
6:57
all working relentlessly towards a single endgame, where learning through execution is actually the modus operandi.
7:07
And so let me give you a couple of examples.
7:09
First of all, I mean, we spent probably 80% of our time on execution.

10 MINS LATER

17:24
What are the key characteristics of an audacious leader?
24:26
But also be fast about admitting when it's looking like it's not going to work and pivot again and learn from it.
24:34
Well, it's pretty obvious, but one of the problems that people have is that they operate without context.
24:42
And I want to talk to you that a little bit, because without context, you can't execute.
24:49
Or if you do, you're executing without some sort of picture of the end game you're looking for.
24:57
And so my kind of mantra around this is you need to be context led and execution driven.
25:04
And what I mean by that is the context piece should only occupy about 20% of your time.
25:10
The execution piece in terms of thinking should occupy 80% of your time.

6 MINS LATER

31:13
Where did that idea originally come from?
Kavon KayeHOST
5:13
Yeah.
5:13
Being different is about being special in a way other people care about, okay? So going back to this challenge, um, we had to look for literally in every nook and cranny of this business, we had to look for opportunities to be different, and it started with the planning process.
5:30
I remember thinking, "Wow, I mean, I, this is a huge...
5:33
I mean, I'm gonna either make this thing or it's gonna break me, one or the other.
5:36
What am I gonna do? I don't have a strategy." And so I looked around, uh, at traditional, um, uh, planning models, and none of them were helpful.
5:44
Okay? It took too long, they were too complicated, and they were way too expensive.
5:48
So I had to create my own.

29 MINS LATER

Kavon KayeHOST
34:55
Yeah.

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