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Keepin’ it 100 with Jesse Osborne, Tipalti

Keepin' It 100 is a series of five-minute episodes of bite-sized tips and encouragement for revenue practitioners.


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Our guest for this episode is Jesse Osborne, Senior Director of Sales Development at Tipalti.

“Listen to your people and give them the platform to be heard. Not just through questions in a big conference call where anyone has questions at the end or an anonymous poll. Do it with them in person. It'll make them feel a lot more engaged. I guarantee it.”

From working at big box companies to mixed-bag startups to joining a rocket ship at Tipalti, Jesse shares the team exercise he does to gain alignment and start winning on day one.

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Jesse is an experienced sales leader with a passion for building and leading high performing sales teams.

Transcription

Nelson Gilliat: I'm Nelson Gilliat with Usergems. And today I'm keeping it 100 with Jesse Osborne, Senior Director of Sales Development at Tipalti, an accounting software company for accounts payable. Jesse shares a number of insights, revenue leaders that are newly hired or thinking about making the jump to regularly obtaining feedback from your team on what they should stop doing, what they should start doing, and what they should continue doing.

So you can implement bottom-up solutions that are more likely to succeed from working at big box companies to mix back startups, to joining a rocket ship at Tipalti, here's Jesse's advice. So you can be your best and key moment. 

Jesse Osborne: I've done this twice now at two different companies going in your first month and do a start-stop until you exercise.

And here's, here's how I set it up. You take three different colors. Post-its like a blue, one pink, one, and a green one or whatever. Uh, you put everybody in a room and you say on the yellow, post-its write down what we need to stop doing. What's wasting time. On the blue ones, write down what we should start doing.

What do you guys have been saying? Like, Oh, we should be doing this, and no, one's listening to me. And then, and then what are some things we should continue doing? Right. And maybe invest more. I'd put that on the yellow post-it Lima loan for 45 minutes. You come back in and have them put all their post-it notes on the wall, and then you start picking them off.

I'm telling you it's the most engaging exercise that I've been able to do, with the team. That's how you can't do what the team of like a hundred people. But if you've got a team of say five to 15 people really, really effective, because then you start to see those common themes. You start to see the well everybody's asking about X.

When I did this at Tipalti, II did this with my team in the first week, we had 12 SDRs on the team and 11 out of 12 people put, we need to redo our quotas. They don't make sense. I don't know how to calculate my own commission. Everybody said that. So by noon. On my first Friday, I sat down with our CFO.

We ironed out a new quota and a comp plan and rolled it out that Friday afternoon and the team loved it and we haven't changed it since. And that’s my point, like that may have taken a while to, to uncover that, but listen to your people and give them the platform to do it. And it's not just through anonymous questions, right?

Those are hard to do, like in a big conference call where anyone has questions at the end, right. Or like here's an anonymous poll. Do it with them in person. It'll make them feel a lot more engaged. I guarantee it. 

Nelson Gilliat: Do you have a note of encouragement or insights to share email me and we'll get you on the show podcast@usergems.com