Herding Squirrels Ep 14

Podcast Host

Oct 22

Written By Brandon Wetzstein

w Adam Tal

Director of Payments Engineering, Vimeo

Herding Squirrels Podcast: Adam Tal - Building Teams That Thrive in Complexity

Guest Bio

Adam Tal is the Director of Payments Engineering at Vimeo, where he’s spent the past five years leading the teams responsible for Vimeo’s global commerce systems—from billing and payments to fraud prevention and compliance. His career spans multiple industries including fintech, edtech, fashion, and consulting, giving him a unique cross-industry perspective on how technology and business intersect. Adam is passionate about building teams that thrive in complexity, where trust, autonomy, and growth fuel meaningful work. When he’s not leading engineering teams, you’ll find him in the suburbs with his wife Kim, son Daniel, and dogs Lady and Norma, or getting his workout in at Orange Theory.

Episode Overview

You’ve felt it before—that moment when your team just works. Everyone knows what they’re doing, has what they need, and you’re all moving in the same direction. But you’ve also experienced the opposite: the chaos, the misalignment, the daily fight for relevance. In this episode, Adam Tal uses LEGO bricks to build the difference between these two realities. Through hands-on models, Adam reveals what separates teams that thrive from teams that merely survive, why staying at an organization long enough to see the results of your decisions matters more than you think, and what new leaders need to know about supporting rather than directing their teams. If you’re navigating organizational change, leading through uncertainty, or wondering how to create stability in a fast-moving environment, this conversation is for you.

Episode Timestamps

[00:00:01] Introduction to Herding Squirrels podcast and Adam Tal
[00:00:37] Adam builds a model about himself—family, nature, Orange Theory, and suburban life
[00:01:36] The best team experience: Purpose, resources, transparency, and good vibes
[00:03:32] The nightmare team model: Panic, misalignment, and fighting for relevance
[00:06:11] Building a model of what keeps leaders up at night—strategic alignment, market uncertainty, and AI adoption
[00:08:38] The challenge of balancing high performers with those falling behind
[00:10:18] AI’s impact on teams: The full spectrum from moral opposition to enthusiastic prototyping
[00:14:01] Why you can have both amazing and terrible experiences at the same organization
[00:15:22] The value of staying long enough to see the outcomes of your decisions
[00:16:24] Adam’s leadership advice model: Building a stable platform that protects the team
[00:18:03] Final reflections on building with LEGO bricks

Notable Quotes

On great team experiences:
“This is somebody with purpose. This is somebody happy and productive. And they are walking with purpose directionally... The base of it, the yellow, I would say, is sort of objective. This is a person who knows what is expected of them. And then this green piece is, I would say, the resources they need to get the job done, right? They know what is expected of them. They have what they need to get the job done. And then the top one is transparency and clarity and feedback.”

On nightmare team dynamics:
“I mean, this is the opposite. This is a complete mess. This is panic. This is misalignment... You have a lot of members like this, and there’s no comfort here. There’s no progress. You’re fighting for relevancy, and every day you sort of have to start from scratch and redefine your role and your position.”

On leading through change:
“Things happen. Leadership changes, product direction changes, market conditions change, and it’s very easy to disrupt the comfort zone of, you know, I have my purpose, I have my resources, I have my feedback, and, you know, I just want to do my job, and I want it to be sort of consistent, and sometimes you don’t get that, and so you have to... You have to maintain this balance of living in the present and doing your job, but also evaluating how is this going to change and is it changing? And if things are going bad, what is bad about it? Who can I talk to about this and what can we do about it and how quickly can we react to that?”

On tenure and growth:
“I encourage people to stay at an organization long enough to see some change. Hopefully, you stayed in the organization long enough that you can make some decisions and then see the outcome of those decisions and the results over the course of a few years. That’s very powerful because someone’s going to ask you one day, can you tell me about a decision you made and how it turned out? And everything looks great on day one.”

On AI adoption:
“Generative AI tools that are available to us, they’re tools. They are a means to an end. You should experiment with them because you might discover that you can use it for something that you can have an outsized impact. You might be able to leverage this tool to create more value.”

On leadership:
“Your job as a leader, you’re making sure that there are people on the platform, there should be a team, that they are the right people, that they know where they’re going, that they’re going in the same direction... The leader is underneath of them supporting the team and building this stable platform.”

On the LEGO Serious Play experience:
“Fun. Yeah, challenging. It’s great. It’s good to have something... Keeps you occupied. Helps you think. It was actually delightful.”