Poshmark CMO on How Adaptive Leadership Skills and a Team-Centric Approach Fuel Success

When Steven Tristan Young, CMO at social commerce marketplace Poshmark, started his career two decades ago, he knew he’d be doing so with the goal of leading a marketing team like Poshmark’s: one focused on brand strategy and aggressive, yet thoughtful, growth.

After taking on roles as a marketing leader at American Express, DirecTV and Grubhub, Tristan Young now wants to leverage Poshmark’s position as a company that straddles the line between traditional retail and digital disruption.

The veteran marketer spoke with us about the leadership traits necessary for success, how he applies those traits to his role at Poshmark, and why taking a team-oriented approach is crucial to bettering a company in the long run.

What leadership traits and skills are necessary to be a successful CMO in 2019?

I’ll give you three points: First, you need to have the ability to really think about how the technology that we use to drive marketing is constantly changing. What I mean by that is, how you do things for the next two years could change three years from now. You have to be able to resist holding on to sacred cows and have the flexibility for continuous learning.

The second one is to always counter. I'm a data-oriented person, but I am the same person who will say, "Data is not always right," because data can be manipulated to a point of view. What you always have to think about is, do you have the right information? Are you questioning information the right way? Do you have enough to make a decision? And what else are you missing that you're comfortable with?

No. 3—this is something that I take from a lot of my experiences—is that integrated marketing always matters. These days, I've noticed that a lot of companies are saying, "Well, here's my brand team, and here's my growth data team, and they don't really have to work with each other."

The harder exercise is to be the kind of leader who shows people how it works, vs. lazy leadership, which is just saying, "Let them figure it out. I don't have to think about how the two intersect."

Keeping these traits in mind, can you expand on the role you’ve played over the past year with Poshmark and what you’re prioritizing for the year ahead?

My main priority in year one was to really understand my team, develop my team, and understand where we can add and move things around—because that's the team that I think is going to build whatever we want to build in the next few years. I didn't come in and try to burn the house down within the first three months, because that wasn't the ask. The ask was, "How do you evolve the team?" And evolving is very different from transforming.

I was also focused on really having message clarity. This is where we start to understand how we create the brand. Most people often confuse brand with just visual design. That's not actual brand strategy. Brand strategy is telling people what you want to be when you grow up and knowing how to make people believe in that. I knew I didn’t want to do that in year one. I want to do that in year two and three—because once I know the team's build and how the company functions, I can be a much better steward of evolving the brand, vs. having to slip in information from external.

As you're working to achieve these goals, what constraints are you working under?

The most important is attracting and retaining talent. I recognize how I'm constantly being pitched different opportunities, and so are members of my team. If I want to create the right incentives for them, I use that Richard Branson line: "Train people well enough so they can leave, but treat them well enough so they don't want to." I can't compete when someone gives you 50% more money, but I can compete when I say, "I'll help develop you. I'll help you grow, and I'll give you depth in your work." I think that intrinsic value matters so much more to people.

How are you driving engagement within your marketing team and strengthening the team’s core?

One of the things that I wanted to make sure the team did was have the proper time to get together to focus on, not just personal development, but group development. I’ve done this in two ways: group off-sites and weekly team check-ins.

In the past year, I’ve organized a couple different off-sites to cultivate our group dynamic. These activities help people understand how to work together. It’s important for your team to know one another as people—not just names and titles—and to understand how and why they work the way they do. As you're scaling and moving faster, you know what you can rely on from people.

I also instituted weekly check-ins with my team, because the larger the team gets, the harder it is to meet. These weekly meetings are actually where we share others’ work. Sometimes people aren't good about sharing their successes, wins or what they've learned. But if you institutionalize it on a weekly or biweekly basis, other people are actually learning more from those meetings—how to speak, how to share information, how to share results—so that they know what it means to run a project well, and it's not just in a vacuum. These initiatives are good for team hygiene and creating what I call "synchronicity in mindset," which I think is what great teams are about and ultimately leads to better results whatever the goal might be.

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