Employee Spotlight: Sky Wolfe

Parker, Smith & Feek Account Executive Sky Wolfe went from small town Idaho to the big city of Portland before discovering the freedom of the insurance industry. Learn more about his love of music, sports, and more in our Employee Spotlight

What’s your role at PS&F?

I’m in a producer role, so I’m bringing in new business and serving existing clients in the real estate and development world, as well as some food and beverage companies. I’ll be officially joining both the Real Estate and Food Resources Practice Groups.

What got you into the insurance business in the first place?

I graduated college back in 2007, which was not an awesome time to enter the workforce. I was keeping myself busy with a few odd jobs, one of which was valeting at a steakhouse downtown. I was trying to be creative about getting my career off the ground despite the poor job market at the time, so I had little business cards made up with my resume details that I would hand out to folks when I parked their cars.

One of those cards worked, and I built a relationship with a gentleman who was a regular and owned a small insurance brokerage in Portland. He asked me what I knew about insurance. I answered honestly and said, “Not much.” He suggested that I come and meet with him and his partner at their offices, so I did.

I liked both of them a great deal. They were both musicians like myself, and were looking for people to come in and help grow their company. Basically, they told me that if I was interested in the industry and passed my license, that they’d  pay for it, give me a small salary and a desk, and I could go after whatever kind of clients I wanted.

That freedom is what initially spurred me to accept their offer; I could work with anyone and any business I chose. Everybody needs insurance, right? So, I started going after the kinds of businesses that I enjoyed – food and beverage places, restaurants, entertainment spots, live music venues, and the like. From there, I’ve just worked my way up to where I am today.

What’s going on in the insurance industry right now that’s particularly exciting to you?

It’s all about disruption. The world is changing incredibly fast, so those who can adapt quickly will come out ahead. Those who aren’t as flexible will fall behind, and eventually their business and clients will suffer.

That’s what excites me right now, is watching the current cycle of change and seeing how the industry is adapting. We are all changing how we look at, transfer, and manage risk. There’s been exciting advancements in blockchain technology, and our firm specifically has developed capabilities that allow some certificates of insurance to be created with minimal human touch points and in less than fifteen minutes.

Parker, Smith & Feek Account Executive Sky Wolfe went from small town Idaho to the big city of Portland before discovering the freedom of the insurance industry. Learn more about his love of music, sports, and more in our Employee Spotlight

Tell me about your family?

My wife is from Boston and moved to Oregon about 13 years ago. She’s a realtor in Portland with a company called Urban Nest. We have a lovely little spitfire of a girl name Phoebe Rose Wolfe, who is in full-blown toddler mode and turned two in July. We’re just now starting to look into getting her into the kind of pre-preschools.

But we are very excited because we have a little boy coming literally any day now (due date is October 17th). His name will be Malcom James Wolfe. I know that you can’t play god or predict what kind of person your kid will turn into, but we’ve already created a life for him before he’s even born (laughs).

My mom and dad are still around and live in Sun Valley/Ketchum area in Idaho. My mom’s a retired postmaster, and my dad’s a jeweler (and hoping to retire with mom soon). I’ve got a brother in Bozeman, Montana and a sister in Denver, Colorado, too. We’re definitely a family of outdoors folks.

We talk a lot about the PS&F difference. How do you make a difference for your clients?

First and foremost: communication. I am a strong believer in the ability of good communication to solve most problems. When it comes down to it, buying insurance isn’t a terribly complicated transaction. The real challenge is ensuring you have the right folks assessing your business needs and risks, and designing programs that intend to and accomplish covering risks and losses.

As the service provider, it’s my responsibility to set things up and be available for my clients. I need to anticipate their needs and be proactive about reaching out. I like to think that I’m pretty successful on that front.

What’s something your co-workers would be surprised
to learn about you?

Well…I am a DJ (laughs).

A lot of times it feels like the life insurance commercial where they take a DJ with long dreadlocks, clean him up and put him in a suit, and have him talk to people about financial planning. After responding that they would buy from him and trust him as a consultant, he busts out his DJ outfit and totally blows their minds.

The only difference is that I actually know what I’m talking about when reading insurance policies and consulting.

You’re a DJ? Do you play any instruments?

Yep! I play guitar a little bit, and grew up playing the piano. My whole family was very musical, and my mom got me into lessons early. My wife’s a bit of a country fan, so we went up to the Kenny Chesney concert in Seattle.

Personally though, I like all kinds of music. I grew up on everything from hip hop to more of the melodic music. I like a little bit of house, a little bit of dance, anything that gets people going. But I also like some Bon Iver when the mood is right. I’m all over the place.

You have a unique name, is there a story behind that?

When I ask my mother why she picked Sky it seems she tells me a different story every time. It really boils down to she was very spiritual and musical after she moved west from New York when she was old enough to drive. I was born in Snohomish Washington and we had a little farm house with a few animals, horses, chickens, and apparently an eagle. We moved when I was three so I rely on my mom for details but she saw the eagle flying in the sky and had an epiphany that I should be named Sky.

Remember…my parents were very musical, spiritual people.  Hard to forget a Sky Wolfe so it’s helped in many situations.

If you could change one thing about the insurance industry that you could change what would it be and why?

I’d have to say the speed of the industry. If you’re a consumer, procuring a policy is a pretty slow and clunky process. Why does securing a policy from the carrier over to you take three months? Anyone can go online and get an auto insurance quote, and bind it as quickly as you can type. But commercial insurance is still so archaic. This goes back to my earlier answer about disruption, because within that frustration with how the system operates is my excitement for the coming solutions. Technology will start to catch up and things will become faster for the buyers.

Parker, Smith & Feek Account Executive Sky Wolfe went from small town Idaho to the big city of Portland before discovering the freedom of the insurance industry. Learn more about his love of music, sports, and more in our Employee Spotlight

So you grew up in Idaho. How did you make your way
over to Portland?

Essentially, it’s because I attended the University of Oregon. I went to the University of Idaho my freshman year on scholastic scholarships. I wasn’t for me; it was just…too small of a town and environment. One of my friends was going to school at U of O, had a house in Eugene with an open room, and offered it to me for a while. I really enjoyed it there, so I started working and got my residency for in-state tuition after a year.

After graduating, I moved in with a friend in Portland, got my first job in the industry as I said earlier, and never looked back.

Is there anything that you miss about Idaho?

I miss the wildness of it. I rode motorcycles growing up, and being able to just jump on a bike and take off and clear the mind was amazing. I grew up in a place that had one road in and one road out. It didn’t matter which direction you turned, you were headed towards the mountains. The only choice you had to make was whether you wanted to go to the Sawtooths or the Rockies. I miss being able to get off the grid for a while.

What did you want to be when you were growing up?

I was big into sports, so I definitely wanted to be a basketball player. I started playing at a very early age and developed some advanced skills, but unfortunately my genetics weren’t as advanced. My ceiling was 5-foot 9-inches.

I could still dunk in tenth grade though, so that was a highlight (laughs).

Are you still a sports fan?

Right now with a baby on the way, my time isn’t necessarily dedicated to sports…but yes! My dad was a big Colts fan, so I grew up watching Peyton Manning lead the team.

I’m really into golf, football, basketball, tennis, as well as the mountain activities, like snowboarding a skiing. A good number of my friends from growing up have even become professional snowboarders or Olympians.

What’s the best career advice you’ve ever received?

You should always be trying to push yourself beyond your comfort zone. If something begins to feels comfortable to you in your job, then you’re probably not working hard enough.

That came from my mother; she was an incredibly hard worker, and I took a lot of my dedication and work ethic from her. I’m a very busy body these days and I like it that way.

What’s kept you in the industry for so long?

Definitely working with good clients and people whom I respect. As far as working with real estate specifically, I really enjoy seeing the owners, developers, and architects make places. We’ve all heard people talk about placemaking nowadays, but when I actually get to be a part of that process and see it before it’s completed, that really excites me. Especially if it’s something that may not come to fruition for 10 years or longer. Being an integral part of the project keeps me invested, if you will.


Where are you from? Sun Valley/Ketchum, ID

Family? Mom, dad, sister, brother, wife, daughter, son on the way

Favorite vacation spot? Gearhart, Oregon

Favorite food/meal/restaurant? Tacos, or my wife’s cooking

Portland favorites? Alberta Street (Bunk Bar, the Radio Room, Three Doors Down Restaurant, and more!)

Childhood heroes? Tiger Woods, Michael Jordan, Karl Malone, Clyde Drexler, Joe Torre

Interviewed and edited by Sara Brauchla, Parker, Smith & Feek’s Marketing Specialist. She is our dedicated copywriter and editor of all published materials, including spotlights, which offer a peek at who our hardworking employees really are when not consulting on our clients’ insurance programs. Stay tuned for her next installment, and refer to our blog or articles page for more of her work.
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