Did You Miss It? Ask Me Anything with Jesse Dondero

Recently, we put Cultivator Jesse Dondero in the hot seat and allowed the Cultivators Community to ask him anything. It got pretty scandalous.

Just kidding. But, we learned a lot.

Jesse Dondero is Director of Program Management and Production at Sessions and Former Global Platform Operations Lead at Uber. He came prepared to ask questions about scaling teams, creating business processes and policies, experimentation, and more.

What was one of the most challenging policies you had to put together, and how did you get through it?

When I started on the Rides side of Uber, I joined a business policy sprint where we re-wrote every business policy. This meant coming up with responses for as many edge cases that came in for each one. The policies ranged from what happens when someone cancels a ride (which costs the company >$100MM a year) to what happens when somebody sexually assaulted someone.

The hardest were sexual assault cases and alleged arrests. We spent a lot of time making sure we accounted for what happened, who reported the incident, and what resolution we could offer. Most importantly, we discussed how to talk to someone accused of being arrested (before we had any proof) and someone who reported a sexual assault (we have specially trained agents for this).

We also had to read a lot of support tickets. My favorite was one from Florida (#FloridaMan), who robbed a bank and took an Uber from the scene. He only got caught because a snake got stuck in the engine, and the car broke down!

What have been your experiences experimenting in a corporate environment? How have you helped get people on board with experiments if they have a bias towards wanting things to be done in more of a big bang, buttoned-up approach?

I think of experimentation in two buckets, controlled experiments(e.g., an A/B test) and uncontrolled experiments that are still intent on learning something about a hypothesis (e.g., testing a new business model to see if people react to it or not).

I've experienced both. First, the Uber Eats app and second testing new businesses that worked within the Uber ecosystem.

The first type is easier to sell. You can tell someone how much of a change you think you can see and that you'll be able to give them meaningful business insights that they can use to drive the business forward.

The second is more challenging and generally requires some leadership buy-in. For example, we wanted to test a new way to pay in stores using the Uber app. We finally convinced the Chile country team because the region generally has lower credit card penetration and saw the product's benefit. That said, it still took constant iteration to make sure we met goals and expectations.

If you have any experience with more risk-averse organizations that are less likely to experiment, how do you think individual contributors can help shift the culture to embrace a more experimental mindset?

In a case like this, I think the goal is to start small and show what kind of return you can offer to your stakeholders. When I started on Eats, there was already a ton of experimentation happening though surprisingly less on a restaurant's menu. 

I see a menu like a restaurant's version of a product catalog, and that Eats should be doing the same thing that Amazon does (fluctuate pricing, group items, price high margin items higher but get people into the restaurant with a loss leader, etc.).

It took an experiment that manually changed the order of menu sections to see if we could increase revenue and show success to get our product team's attention. Once we consistently showed success with improving revenue, we could get more support and start testing even more at scale.

In the end, it's starting small to show that there's an advantage to trying new things, and over time it will develop into a core competency.

How do you navigate managing competing personalities and egos when building a team and navigating complicated business processes?

I have a few points.

1) It's way easier to navigate processes if you take the time upfront to study them and track down the person who wrote them to understand their intention. They often wanted the same outcome you're going for, but they weren't able to get there through restrictions at the time.

2) Share success - As I said in my last post, people want to feel heard, even if they would do the same thing as you. The earlier you bring people in and the more credit you share, the less likely someone will get in your way.

3) Always include legal, especially in large companies. I can't tell you how many times we started something to find out later that there's a perfectly good reason why we can't do what we originally intended. If you work with legal early, they're often very helpful in giving you guidance on creating something that is not going to break any laws.

What's the most challenging part of making change happen inside a large organization? And what would be your advice for changemakers?

Building relationships and territorialism.

My advice is to build relationships within your company because people who know and trust you are way more likely to listen to you when you come up with something that might be a little out of the box. They're also way more likely to support you and stick up for you, especially with leadership.

On the other end, be ready to engage with people who, if you're successful, might have to adjust what they're doing to accommodate your success. In many ways, I think being a leader is doing the work and then stepping back and letting other people have a hand in helping make your project successful.

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