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- Insights from a Design Leader: Maria Pentkovski
Insights from a Design Leader: Maria Pentkovski
Maria has led successful design teams and is the founder of Careercoach.design

I’m travelling and I regret not bringing my podcast-level mic for this narration 🫠
Intro
This week, I have the pleasure of chatting with Maria Pentkovski, an experienced design leader and hiring manager whose practice is deeply human and rooted in craft. She started her career in the early 2000s and was interested in showing the value of design as it relates to business.
I’m excited to do this more and hope that these conversations help meet readers where they might be at. Let’s go.
Maria PentkovskiDesign leader, Founder of Careercoach.design For most of her career, Maria has been leading teams and initiatives of all sizes. She has worked at iconic companies such as Upwork, Evernote and Turo where she built incredible teams who under her leadership shipped many growth experiments and 0-1 designs. Maria is an inspiring leader, trustworthy partner and an overall good selfless human who is always open to feedback and practices highest integrity in all her actions and decisions. | ![]() |
In addition to her career in tech, Maria is a career coach working with designers of all levels to help them navigate and conquer the job search, interview process, and their careers. Check out her website or book a session with her here!

After chatting with Maria a bit over the past month or so, I thought she’d be a great guest to have here due to her extensive experience building design teams. In future posts of the Un-Employer, I’m thinking of including video or, at the very least, audio interviews for those who prefer to watch or listen. Let me know by replying here or reaching out on LinkedIn if that’s something you’d be interested in.

What experiences or decisions helped shape your path into design?
I was always passionate about design for commercial purposes. I loved things like school supplies, packaging, billboards, and commercials. I also always got a kick out of the design details — looking at the back of the box and seeing all the tiny print arranged along with the barcode was fascinating and incredibly satisfying.
Then when I was in high school I realized I was a good drawer and painter. It was nothing groundbreaking, but I could do more than an average person and enjoyed the process. Going to a regular college didn’t appeal to me much, so I went to art school, where I found my path and a place where I felt like I not only belonged but could also inspire others.

What’s a project you’re particularly proud of, and why?
One that comes to mind is a vision project I initiated and led at Turo that drove real organizational change and greatly enhanced a frustrating experience for customers.
We uncovered a neglected area in the core product that contributed to an astronomical volume of support calls. Through this vision work and strategy, a new product domain was formed to bring it to life, resulting in a substantial reduction in support call volume.
Side note from Nick: It’s not always the super sexy visual projects that become favorites throughout your career. I’ve worked on many projects that were either more on the back end or internal tools-focused which I had a great time with.
Okay, back to Maria.

How has your approach to UX changed throughout your career?
When I first started my career, there was no UX. Design was very selfish at that time. But, I learned UX inadvertently when I started my career in the growth initiatives without even realizing it.
I worked on acquisition funnels and learned that creating journeys that focus on the user as opposed to only focusing on the business, tend to impact that business the most. Today the landscape is changing all the time, and I’m trying to stay aligned, even ahead of the changes as they impact UX (of course, AI is top of mind for me, and there is so much potential there).

What skills or qualities are important for those looking to move into leadership roles?
Autonomy: You need to be able to work independently of others while owning your work to progress it forward.
Curiosity: Explore new perspectives and approaches, even for small tasks.
Empathy: Give a damn about others and see the world through their eyes.
Grit: In design, and tech in particular, things often change faster than any of us would like. That’s the nature of the game, though. This industry is not for everyone, and especially when going into leadership. Do it with a purpose, represent your team with pride, get work done that makes a difference.
You should want to be in leadership for the sake of others, not for selfish growth reasons.

Another side note, but I love something that Netflix includes in their culture memo that says “disagree then commit.” Meaning that even if you disagree with the direction of a project, you’re still on the same team that wants it to be successful.
Alright, let’s shift gears a little and talk about how Maria builds her teams.

As a design leader, what are some things you look for when building or growing your team?
I hire great people!
I hire people who want to be in the company and team, who bring in expertise but are also wanting to learn new things (Maria’s law of Curiosity that I, Nick, just made up), people who are selfless and want to be a part of a team, people who own up to their actions and expressively learn from them, and overcome challenges (Maria’s laws of Autonomy and Grit).

What is your view on design portfolios?
Your portfolio is so important, and I can’t stress it enough, it shouldn’t have a speck of dust on it. Every pixel and punctuation mark matters, but only if the story is there. In terms of the format, it is unique to each person—their work, their style. Whatever format you choose should enable you to tell a good story. I have seen way too many deathly boring case studies, but once in a while, one is told in a relatable way and shows not only how the project was done but how YOU (the designer) specifically went through the journey and how it impacted your own growth. | I’d recommend having a version that works with and without a voiceover, in case you’re not there to walk someone through the work. Make it accessible on desktop and mobile. I know that not all hiring managers are looking at portfolios on their phones, but you should ensure it looks great on all devices. Make it simple and elegant. Whether your medium is a website, a deck, or video - I personally don’t think it matters! It should look good and tell a good story. |

What advice would you give to those navigating the wavy waters of today’s job market?
I am not a quitter, and I think it comes from my immigrant mentality. So, I say to anyone who wants to be in this industry (design specifically) - stick with it but don’t expect to sit and complain or wait for “markets to get better.” You have to work hard to earn a spot in this industry. So here are the main pieces of advice:
🎨 Make sure your design is high polish (AKA craft) - this means design foundations like color, type, composition, and grid. If you didn’t go to art school, you should take a graphic design foundations class - it will teach you a lot!
📖 Tell a good story: Make your portfolio engaging, interesting, and fun. Steve Jobs was one of the best storytellers. If you haven’t seen it, watch his Stanford Commencement speech and, of course, the MacWorld keynote when he introduced iPhone.
🛜 Network: Make connections, extend yourself to help others, contribute to the community. Don’t expect anything in return, and, if you are selfless in your networking approach, people will have your back when you need it most - our community is incredible.

Gif by NickCageMovie on Giphy
🚀 Stay Inspired/Informed
Job Market Articles & Resources
Careercoach.design (where you can book sessions with design leaders and career coaches like Maria)
“Grit” by Angela Duckworth (for those interested in learning more about this quality and how you can use it in your life)
“The First 90 Days” by Michael D. Watkins (for those who may have started a new job (CONGRATS, BTW), this is a book that outlines how you can plan out your first 90-days at a company)