Inside The Mind of Design Leaders Ft. Director of Product Experience Design at Mastercard

By Kristie Craft

Within this blog series, Kristie sits down with Design Leaders across the industry to get their insight into their successes, challenges and advice. This week, Kristie speaks to Jess Greco, Director of Product Experience Design at Mastercard.

Kristie: Could you tell us a bit about yourself and how you got into design?

Jess: I'm a Design Director at Mastercard. There are many directors like me across our offices, but I oversee Design and Research for one of our products—this product happens to be one of the only products that is B2B and B2C. However, Mastercard is a huge Enterprise Technology, Financial Data and Services company. So, this is an evolution for the company.

I have Design, Research and Content Strategy working together on my team to deliver an experience that meets business expectations, but also works for our customers and their customers.

I went to college for Fine Arts. I studied Art History and Psychology. I wasn't really thinking about getting a job afterwards. So, I bounced around and did a bunch of things. I was super interested in computers and I figured a mix of computers and art could be a good way to be more employable and to always keep learning… all those good things that are double edged swords!

I went back to grad school for Computer Art. They taught us all sorts of things, some of which were more useful than others, but all of it really taught me how to learn and how to teach myself. I came out of it doing a bit of programming, a bit of design, a bit of robotics, a bit of sound art, and got a job doing design and programming.

This was around the 2008 crash; I got a job six months before graduation and just hunkered down. UX was still a new term and I wanted to be a part of it. I’m a voracious reader, a sponge, and I just kept trying new things.

Over the years, I had a bunch of different jobs… and as it turns out, when you look for jobs that are consistent with your interests, you wind up with a coherent narrative at the end without intending to. I really like working on enterprise things that are also consumer-facing; I like working on complexity.

My career path wasn’t really planned, and the industry was in a totally different place in the mid-2000’s. There was so much less that you could do in 2005.

As things begin to come on to the internet, you needed someone to help organise things, make them coherent and make them usable. I'm good at learning new things, adding things in and making it all coherent. I've worked as a designer, I've worked as a researcher, I've done content strategy work. All of these things go into providing a coherent experience for people.

Kristie: How is your role positioned within the business?

Jess: We have disciplines and each has a discipline lead. For instance, there is a content strategy person on our leadership team who is the resource for all of the content strategy leads, but they’re matrixed to my team. I also have designers and researchers that report to me directly. I'm still working on hiring official researchers, so sometimes we have consultants, sometimes we do it ourselves. I've also been teaching my team to do more; it's nice to be able to fill the gaps in that way.

Basically, everyone is on my team. Regardless of who they report to, I treat them all equally. We have one to ones and I don't let them get into a situation where people feel treated unfairly. I'm hoping to scale the team based on what we have planned for the year ahead. We are not very siloed at all and we are very much dedicated to our product.

How did you get into leadership? Was that just the evolution of moving around, or was there a clear time for you to step up into being a manager?

It was actually not the easiest step. It was a really hard step. I knew I wanted to, and I was already naturally falling into those situations, but my employers would decline to formalise it—they would be aware of what I was doing and decide not to do anything about it.

I was doing a mix of Service Design and other things in my last roles, but ultimately it got to the point where I realised I could have the most impact by shaping the rules, guidelines and point of view, before we even got to the point where we were making anything.

It was hard, I had to turn down a lot of opportunities and be very clear that I was looking for a leadership role. People don’t necessarily respect that, or they have internal biases that prevent them from understanding. They may not necessarily assume that I'm in leadership, maybe I look too young to them, maybe I'm not what they imagined in their head, maybe I'm too female. I've been with male friends and I've been asked, ‘Oh, are you a student?’ And my friend goes, ‘No, this is the person who helped me have a career.’

My career has not progressed at the same pace as some of my male peers, but I had more horizontal growth than many and I’m well-positioned now.

I'm so glad that I had that time, because now I can run a research team, and work effectively on the product strategy. I can work with my product designers and I can oversee the service design of our product ecosystem. All of those things I would not have necessarily had time to learn to do before. Still infuriating, but it worked out.

Kristie: What are some of the top challenges you faced as a design leader?

Jess: I would say that persuasion and influencing is a skill I've really had to build over time. Sometimes it's not what I say, it's how I say it. If I make the person feel confident that I know my stuff, then they're more likely to calm down. If I sound stressed or answer them in a moderately ambiguous way, their anxiety will increase. Then the cycle of requests for meetings and reviews accelerate. It has diminishing returns over time, because then the team doesn’t have time to get their work done and so on.

I would say that's been something I've really had to learn — it’s much easier to figure out what to say, and it was much harder to figure out how to say it, to give people the confidence in my expertise.

Another thing I've been really learning—and was not good at early on in my career—was de-escalating conflicts.

‘How serious are you about this?’ ‘How strongly do you feel about this issue?’

It’s a conversation that I’ve had with many people, and I’m glad that I can have those now… I would have been too nervous many years ago. Everyone assumes everything is a 10 out of 10. Sometimes it’s not, or sometimes they need to know why it’s not as big a concern as it seems.

Sometimes we debate about how serious an issue something is, and it’s great to be able to prove or disprove hypotheses. A lot of what I do is making sure everything is vetted through the process that we have before we show it off. Sometimes that means a proposal will come out of the blue from design and product to our executive team. At this point, they know that if I'm proposing anything, I’m confident it will work.

It’s exciting to have all of these pieces available to me at my current job, because at past jobs, I might have had part of it, but not all. Running the team in a way that is driving results without losing sight of people, learning how to get work done through others, coaching them to do the things that we need in the way that they feel is best.

I'd say my biggest challenge right now is coaching my design leads to not compromise pre-emptively.

Someone will ask a question, like, ‘Why'd you do that? I'm not sure I agree.’ Then they immediately jump to ‘We could do this instead.’ I want them to feel confident in their point of view and advocate for great design. What is the platonic ideal? Why do you think it should be this way? They're not saying change it… yet.

Getting them to express the rationale without panicking, that's what I want to happen. I want to up level my whole team so they can work really effectively with the stakeholders—without me needing to be there to facilitate.

Kristie: Do you have a design philosophy that you live by?

Jess: I just think that experiences should be as simple as possible, and they should tell you what's going on. So whether it's an enterprise experience or consumer experience, there honestly shouldn't be a difference. There are different amounts of expertise your audiences have, so you can have varying amounts of information, but ultimately, it should be obvious what you need to do. It should be appealing, and you should want to do it.

Some of these companies still think, ‘Oh, I can force things down people's throats, just force them to use it.’ That's not going to fly in this day and age.

My philosophy is straight talk with my stakeholders and helping people understand why the thing that we're offering them can help them, not forcing it on them.

Being a female leader in the position that you're in now, are there any communities that you're a part of outside your current role that really help you?

I'm a really active member of the Interaction Design Association and started running the New York chapter about two years ago. I think that org does a really good job at creating opportunities for people to learn and understand what's going on globally.

I would say the other group that I really like is Tech Ladies. It's an online community and they do events. It's extremely wel-run and well-moderated, I'm a huge fan.

The other one that I'm a fan of is Women Talk Design. They teach people, women specifically and non-binary folks, how to construct talks and share their ideas, practice them in a safe space until they feel ready to take it to their audience. They do a lot of great work.

Kristie: What qualities or characteristics do you look for in a person when hiring?

Jess: I'm always looking at the work itself. There are so many factors that go into that work and that shape it. What opportunities you were given, the way you capitalised on them. I’m looking to see if you just did what you were asked or if you went further, if you could see another opportunity that you could push, or did you try a different technique that added some value.

I'm also curious about process. I'm a huge process nerd because process is the way that we scale our impact. What I mean by that is, if your process works in multiple situations, that means by following the process we are more likely to have better outcomes. That doesn't mean the process can't flex, the process is flexible by nature. I'm looking for their level of flexibility and understanding of different ways of getting things done. If you're following a super-rigid process, you might struggle with a real-world design environment.

I'm looking at ability to articulate a rationale. Can you explain your rationale for your choices? Why did you do it? What did you push back on?

I think vetting requests is extremely hard for people to do without lots of experience. People are very eager in their careers to just take it, do it, show that they did it and get it done… but I would say that the mark of someone truly senior is the ability to question and reshape the prompt that they were given.

Also I look for a good attitude and openness to feedback. Early in my career, I really struggled with taking feedback well. I felt personally criticised, and I get it, it's hard, but it's not a personal criticism and it's necessary to make the work great. Sometimes we’ll debate an idea and I'll go, I haven't thought about it that way, let's change it. That’s what great design can do when you worry less about being “right”.

I do think it's important for everyone to feel like they have a stake in what's being built and how we move forward. I want everyone to be bought in. Getting my team to be really good at taking feedback, but also influencing people's reactions, and persuading then that their approach is actually going to work… The more I think of myself and my team as advisors and facilitators of good decisions, the better our results become.

How are you guys doing now in the current situation. Was it an easy transition going from the office to working from home?

Most of our team is in New York. We work with partners in Dublin, India and a few other places, but that’s not every day, which has made it easier.

The team has struggled because New York has had several waves of COVID-19. There have been protests, there have been helicopters 24/7. My team has gone through a few phases where they're just physically exhausted because they can't sleep; they live in neighbourhoods that are wild all the time.

Other than that, the team are very close. We were co-located with our Technology and Product partners in a space, and we were so happy to be there. Everyone liked going to the office, we like seeing each other and we like working together. Mastercard is fairly meeting-heavy, remote was not the norm, but everyone has adapted really well.

My team has really risen to the occasion and impressed me by how they intentionally reach across the aisle to bring people in before it's too late, before you're dropping it on someone. It does require more intentional conversation of ‘How do we take this forward?’ ‘Who do we need to talk to?’ ‘Who should we socialise this with?’, but I've also noticed that my team is getting really good at navigating the org.

I'm just super proud. I can't be everywhere at once, so I need them to be my emissaries. The more I impress upon them my goals—without specifying the means—the better the results. I’m just constantly impressed.

I've actually been trying to teach my design leads to be more difficult and to push back a little bit more. Efficiency is good… but after the decisions are made. We have to have those high standards and maintain them; otherwise things get watered down. A lot of the time people will bring “requirements” to us, and we'll actually push back on them and reshape the terms, because people won't realise how questionable some of those requirements might be.

My team has been building their negotiation skills. It's not necessarily the easiest thing to do as a designer, because you think your job is to make things, but actually a big portion of your job is to negotiate the terms that are used to evaluate those designs.

Kristie: Any blogs, books or podcasts? Or any resources that are either helping you now, or have previously helped you?

Jess: I am one of those people that can't listen to podcasts, I can't do it. I love reading though.

I am a big fan of all of the Rosenfeld media books, they're fantastic. I have pretty much every book on my bookshelf. I love those books, they’re extremely helpful and they're targeted by topic. There’s one on Meeting Design that’s just wonderful. I actually buy the dead tree versions because my husband loves reading them too.

I'm also big fan of A Book Apart too. They have a new one that I'm working through which I’m really enjoying.

Thanks Jess!