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Lead Compassionately, with OfferUp’s Vice President of Community and Communications, Natalie Angelillo

Below is an article originally published on Dec 10, 2019, in OfferUp blog. Go to OfferUp's company page on PowerToFly to see their open positions and learn more.

The executive team at OfferUp is full of standout individuals, but there is one among them that is known to always capture the attention of a room: Natalie Angelillo — Vice President of Community and Communications. In addition to being a reputable and accomplished businesswoman in the Seattle tech scene, she's also one of OfferUp's first female executives, and it's a differentiator that she wears with pride.

For almost four years, Natalie has worked closely with our founder, Nick Huzar and the rest of our executive team to help make OfferUp what it is today: a top-five consumer shopping app that is transforming how people buy and sell locally. As part of her role, she oversees internal and external communications, community outreach, and OfferUp's external brand messaging.

One of Natalie's biggest strengths is her history of entrepreneurship. She has worked with a wide range of companies at all different stages, including a startup (PhotoDisc) that became a public company (Getty Images), and many companies at stages in between. She has also founded companies, and been the CEO herself, and is an active board member and advisor to many, currently serving as an active advisor to Styylize and Nonlinear Materials.

She's an empowered female executive, a mom to two, and a proven leader with an entrepreneurial mind, so we wanted to talk to her to learn about how she found her perfect work and life balance, and her rules for leadership success.


Prior to founding your own companies like SteelheadGroup, SwopBoard and Swink Style Bar, you were in visual media with companies like Getty Images and PhotoDisc, Inc. How did you get started in that industry?

I was pursuing my master's in art history at the University of Washington and was interested in the intersection of art, technology, and law. I took what was supposed to be a one-day temp job and was introduced to the founder of a company that was just starting called PhotoDisc.

PhotoDisc was the very first royalty-free stock photo agency. It was a disruptive licensing model powered by technology and I was fascinated by the potential. I started as the assistant to the President and over the next 5 years worked in a number of roles, ultimately running the Content and Product teams. Through a merger and then an IPO, PhotoDisc, Inc. became Getty images. After spending another 2 years at Getty as a public company focussing on organizational development and integration, I decided it was time to try something new.

I had just had my son when I had the opportunity to be the CEO of an event photography startup, PhotoZone. I always say that PhotoDisc/Getty was my MBA and PhotoZone was my PhD in business. We had a great team and concept, but our timing was bad. We expanded to 24 cities across the nation, then the tech bubble burst and we couldn't raise enough to keep going. It was devastating but in hindsight, it was the greatest learning experience I could have had.

After some pretty unique business experience in just 10 years and my second child on the way, I wanted to do something that gave me more personal flexibility and more exposure to a wide range of companies. I started Steelhead Group, my own consulting business, and spent the next eight years coaching and mentoring startups and mid-stage companies. During that time I also co-founded Swink Style Bar, which I eventually sold in 2017, and then SwopBoard which led me to OfferUp.

How did the conversations begin for you to join OfferUp?

I was introduced to one of OfferUp's board members, Serena Glover, who introduced me to Nick Huzar. She thought we could do more good together, and she was right. Nick and I bonded over our shared passion for schools, community building, and funding education, and he convinced me that these interests would fit well into OfferUp's wider vision: empowering people to connect and prosper.

What are some of your personal strengths that have helped you advance in your career as a woman in a leadership position in tech?

There are three guiding principles that I always try to follow regardless of what I am working on: excellence, action, and compassion. I've had so many different roles over the course of my career that it was important to have a guiding framework to anchor my focus.

Excellence may seem obvious, but it's something I consciously work on every single day. Whether its a keynote address or a company email, I believe in working exceptionally hard no matter the task. For me personally, excellence is in the little things, and diving many layers deep to make sure all angles are considered, and all the details have been triple-checked. My team has heard me say it 1000 times, the little things matter.

Action, which sometimes sits in opposition to excellence, is especially important working in a fast-paced start-up environment. Making decisions quickly and moving fast is critical. Coming from an academic environment, where the emphasis is on research and reflection, I had to really work on this skill early in my career. Working with or for startups for all of these years has honed my ability to be decisive and to act fast. Working for Nick has taken it to a new level — I often give him an update on something and his response is, "great, go faster!"

Compassion is something that came to me much later in my career. In fact, I probably would have seen it as a weakness early on, whereas now it's one of my greatest strengths. When you're younger and just starting out, you tend to be harder on yourself, which translates into your working relationships. You expect more from yourself, so you expect more from others. Expecting a lot is great, and I do expect a lot, but you have to balance it by being willing to understand the nuances and the complexity of people, relationships, and how their work fits into their whole life. Leading people as I have matured has become less about judging performance and simply grading outcomes, and more about empowering, motivating and helping people accomplish their very best work. I don't think it's made me "soft," but I do think it has helped me get better results and have more rewarding work experiences, and I think my teams would agree. The compassion piece applies to how I feel about myself as well, but I find it's a bit harder to exercise that self-compassion, and it's something I'm still working on today.

The Community MeetUp Spot program started two years ago and has since grown to nearly 2,000 safe exchange locations nationwide. You've been a passionate advocate for OfferUp to tackle the issue of trust and safety within its community. How did it start? Why is it so important?

We have millions of people looking for a place to meet to complete their OfferUp transactions every year. We are building the largest local marketplace, but we are also building the most trusted one. That means doing things that are hard to scale, and investing in programs that pay off quietly over the long term. Building a program to provide people with places they can trust more than meeting at home or in an empty parking lot was a natural step for us, but it entails measuring success by what doesn't happen, which is as hard as it sounds. Now, there are nearly 2,000 law enforcement agencies participating.

In terms of growth, last year we announced — the only comprehensive national database of safe exchange locations in the nation which is available to anyone, regardless of the marketplace they are using to buy and sell — and launched our retail partnership with Giant Eagle, to bring safe exchanges to local grocery stores in neighborhoods as well.

2020 is right around the corner. What are some of your proudest moments in 2019, and what are you hoping to achieve next year?

I'm so proud of my team. They've accomplished so much this year, and all of their individual victories mean a lot to me; it's an amazing feeling to watch people rise to the occasion when given the chance, explore new skills, and discover things they excel at that they wouldn't have found anywhere else.

Natalie, Head Honcho of the community and communications team at OfferUp, pictured at her desk with her team!

This year is going to be a really exciting one for OfferUp, and I'm grateful to be part of it. I'm looking forward to continuing to raise our profile, elevate the brand, and make OfferUp a household name.

How do you balance having a full-time career and being a full-time mom?

I have two really great examples. My mother and grandmother are the "OG" entrepreneurs in my family. My grandmother had a thirty-year career as a photographer that she started at 65, and my mom stayed home with us as kids, and was always an incredible artist. Once we left for school, she started a successful interior design business which she still runs in California. Their creativity, curiosity, drive, and determination was something I grew up around and have in my genes.

My kids are very supportive and understanding of my schedule. I may not be at every event, or I may bring store-bought cookies to the bake sale, but they know I am here for them for the big and the small moments. I'm incredibly proud of them both; it's such a joy to watch them grow into these amazing humans. They're both independent, capable, and self-reliant because they've had to be, and those are all valuable skills to have these days.

It's important to take time for yourself, outside of work and home responsibilities. You have to find a work/life balance that suits you, even if that means getting up at five in the morning to hit the gym or make it to kettlebell class on time. I start my mornings productively for me, I follow them with being productive at work for the company, and I try to spend my evenings at home with my family.

What does your OfferUp search history look like, and what are some of your tips from over four years of using the app?

  • "West Elm furniture" is a popular search for me — I just bought a brand new West Elm Souk rug for 80% cheaper than the retail price. I've been remodeling our basement and OfferUp as been my go-to for deals on high-end brands.
  • "Kettlebells" — so many kettlebells! I just had a kettlebell sport competition and have been training hard to prepare, using great equipment I found on the app. OfferUp is the perfect place to look for gym equipment — it's usually "lightly used" and people are selling to make more space so you can find great deals!
  • After that, there's "mirrors." Everyone should look up mirror posts on OfferUp — its high comedy to see how people try to photograph a mirror without being in the photo — some of those pictures are hilarious!
Natalie recommends setting a search alert for things you find yourself looking for all the time — that's how she found such a great deal on this West Elm rug!

As for my tips, the first one is don't post anything right before bed. You get so many messages that you're distracted from going to sleep at a reasonable hour. If you're someone who's busy like I am, I think descriptions matter the most. Try to include as many anecdotal pieces of information about your item as possible so that buyers know if it's a good fit for them. Having a good description means there's less back and forth, and you can get to the sale much faster.


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