14 | Jason Siciliano: Marketing and Copywriting

Todays episode we speak with Jason Siciliano who is the Creative Director at SquareTrade, and founder of ModernCopywriter.com. We talk about content marketing, copywriter portfolios, and destroying digital devices for research. 

About Jason Siciliano

  • Creative Director at SquareTrade
  • Formerlly at Target & Yahoo in creative roles
  • Founder of Modern Copywriter

What I try to tell copywriters who are just coming out or just starting to put their stuff together is find a copywriter out there who’s doing it and has a portfolio that blows you away and do that.

Jason Siciliano

Show Notes

Matt: Found out more about him, but welcome to the show Jason.

Jason: Thanks for having me man. It’s great to be here.

Matt: Well, I guess let’s get into currently, what you’re up to these days at SquareTrade. I did check out the website this morning and I love the phone dropping into the cereal. Did you have any play in that?

Jason: Yeah. That’s my team. I’m Creative Director at SquareTrade. I also have Coms. The Coms team here, as you’ve said, do protection plans trying to disrupt the warranty industry which was traditionally known for horrible service.

Matt: Yes. (laughs)

Jason: SquareTrade has just started to find out. That’s all I have to say. SquareTrade kind of came along and flipped out on its head and is now the protection plan provider at most US retailers and we’re in six countries in Western Europe. And we protect everything. You know at Walmart, Target, Sam’s Club, Costco, phones and tablets and electronics to appliances and furniture and all that. So, a big part of my job as Creative Director is trying to bring that to life. Protection to life and act as an advocate for for consumers. So we do a lot of video breaking stuff. Every time there’s a new Galaxy or iPhone that comes out.

Matt: (laughs)

Jason: We have a bunch of robots that we developed with a robotics engineer from Cal Berkeley.

Jeff: How fun is that?!

Matt: I know! I want your job, Jason!

Jason: It’s a blast. I know. It’s awesome. So we buy like twenty-grand worth of phones and go out and dunk them and drop them and bend them and tumble them and stuff..

Matt: Oh yeah.

Jason: It’s super fun.

Matt: Yeah, instead of All State. You just bring the mayhem to your office.

Jeff: (laughs)

Jason: Exactly! Yeah, nice, nice. Yeah, we were acquired by AllState about two and a half years ago, and as they continue to expand what they need as far as protection today for their consumers from auto and home. Do you know they recently acquire- acquired an identity theft protection company and for armor, us, as far as product protection and there’s expanding how they protect people in a more holistic way. And I think you know back in the day, the first insurance plan everyone had was on their car when they were 16 and they got their first car- and I think today it’s on your phone at probably 12 or 13.

Jeff: Mmhmm.

Matt: Yeah, so speaking of all your marketing and history and everything, is there one project that stands out to you that has always been something you’re super proud of? One of your favorites?

Jason: Oh, god. I mean I love the one at SquareTrade that you specifically mentioned, which is our Breakability Campaign. It’s been going for 8 years, 9 years- where we go and test phones with these robots. It’s a blast. The Galaxy fold has, I’m sure everybody’s aware, has had some problems.

Jeff: Yeah.

Jason: Samsung’s pulled back on that. But let me just say, we’ve got a new robot waiting for that to come out.

Matt: (laughs)

Jeff: (laughs)

Jason: So, that’s pretty exciting. There was a campaign probably, I’m trying to think of something real quick, way back in the day. I’m gonna date myself. Do you guys remember InfoSeek?

Matt: Oh yeah. Yeah.

Jeff: Yep.

Jason: So, back in the dot com days, that was the beginning of my copywriting career. That was in the nineties in San Francisco during the dot com boom, and that was just launch after launch after launch, right? And there was this company, InfoSeek, this was before Google dominated everything. And they were a search engine. And the time that we launched them, they were the number three search engine. They were like, “We’ve got a $30 million budget. We want to do a huge branding campaign but we don’t really know what we are, so don’t say anything about us, just make a big splash.”

Matt: Okay.

Jason: Which is the most awesome thing in advertising you could ask creative person to do.

Matt: (laughs)

Jason:  So, we shot this big campaign for the launch of InfoSeek in Brooklyn with Vic Argo, who is this actor that was in every score cities movie. And kidnapped this guy and took him to an abandoned warehouse. And just made, basically, little movies out of it. It was fantastic.

Jeff: Oh man.

Jason: Yeah. Those days were, those were different days.

Matt: That sounds very familiar. I think I remember those campaigns.

Jason: There was a Super Bowl one. That was my one Super Bowl campaigns back in the day. (laughs)

Jeff: (laughs) That’s great.

Jason: Alright, so I’d have to say it. You talked about- kind of breaking phones. Do you remember the, I’m sure you’ve seen it, the blender. Will it blend? Have you guys?

Jeff: Yeah (laughs). I heard that it was a hoax. Is that?

Jason: I didn’t hear it was a hoax. So there’s a lot of YouTubers out there that are doing really crazy stuff with their phones, and I think that we’re taking a little bit of a different attack because we’re an insurance company.

Jeff: Mmhmm.

Jason:  Actually doing real science with it and trying to give the phones breakability scores so that consumers are really informed. It’s still really fun. We’re still out breaking stuff and shooting video but we’re trying to do it in a scientific way where people can look at it and go “Okay. Is the iPhone 10 more durable or less durable than the iPhone 8 or should I wait until the iPhone Max comes out? Is there a real difference?” Our tests are really about how people actually break stuff: drop it, dunk it.

Matt: Yeah.

Jason: That type of thing. Rather than dropping it in a blender.

Jeff: Right. (laughs)

Jason: That stuff is fun. I think if we did that we’d lose a lot of credibility.

Jeff: Yeah. Yeah. (laughs) Makes sense.

Matt: So I have to go back to Scorcher Rate. You talked about it kind of disrupting the industry. Can you speak to that a little bit? What were some of the few things you guys did to kinda set yourself apart from all the other companies that were providing mediocre service?

Jason: Sure, if you want to talk about warranties. Absolutely.

Matt: (laughs)

Jeff: Hot warranty talk.

Jason: Yeah, hot warranty talk. I think the founders of SquareTrade. So, SquareTrade started actually as the arbitration company on eBay and for the first six years of its life, that’s what it was.

Matt: uhuh

Jason: And it grew to a certain size and then the founders looked around and said “Okay, this is only going to get as big as people argue on eBay. So, where else can we take it?” And they looked at the warranty category, which is just a monsterous category. $20,000,000,000 category, and said the service is horrible, there’s no innovation..

Matt: mmhmm

Jason: And the world is changing. People are carrying thousands of dollars worth of glass techno- expensive technology on them everywhere and protection is not caught up to it. And this was right about the time, they were fortunate, right about the time the first iPhone came out. So they flipped it around and started doing protection based on great service. Realized that people shop through ratings and reviews. So, make a warranty that people would be able to research online and see how good it is. And then they changed how the protections were done too by really focusing on accident protection. The old warranty industry was focused on “If your thing just breaks, we’ll fix it.”

Jeff: mmhmm. Okay.

Jason:  And SquareTrade really focused on “If you break it, then how do we fix it as fast as possible?” Because you can’t be without your phone. So, that’s what we keep doing, and today we’re already to the point where, if you break your phone, if you crack your screen, in most places we can get a check out to you in the same day and fix your screen in like 30 minutes.

Matt: Okay. (laughs)

Jeff: That’s amazing.

Matt: Yeah, that’s impressive.

Jason: Yeah.

Matt: Can we test it right now Jason if I.. (laughs) ..break my phone on this podcast? (laughs)

Jeff: (laughs)

Jason: (laughs) Do you have a SquareTrade?

Jeff: Do I have to have your service ahead of time? (laughs)

Jason: You don’t for the SquareTrade go. The cracked screen, you can just pay for that all in cart, on the site.

Jeff: Okay. (laughs)

Jason: Don’t have a plan. But it’s much better if you do have a plan.

Jeff: Okay.

Jason: It’s cheaper, and  it’s crazy that you look at iPhone, you look at the new Galaxies. They’re just getting more and more expensive and they’re loading up with features. And, the phones are amazing, but they’re getting more and more breakable. And there’s now glass on both sides. You drop the thing and crack it, FaceID doesn’t work.

Jeff: Mmhmm

Jason: How you get into it doesn’t work, you’ve got a brick. So, repairs are on the iPhone Max, like $350 for the phone screen and $550 for the back.

Matt: Oh geez.

Jason: That’s a lot of money.

Matt: Yeah.

Jeff: Yeah, going back to my flip phone. That thing was durable. (laughs)

Matt: (laughs)

Jason: (laughs) Seriously. There was nothing wrong with my little Nokia brick back in the day.

Jeff: Yeah, it’s super dependable.

Jason: Really?

Jeff: Just note: no range. But super dependable.

Jason: Yeah, and texting was like…

Jeff: Oh mean, yeah.

Jeff: Three, three, three. Four, four, four.

Jason: Yeah, right. Right. (laughs) Yep.

Jeff: So there’s a question in here that’s peaking my interest. Sorry Matt if I’m jumping in front of you.

Jason: Yeah.

Jeff: The question is: which content, which marketing, as far as content at SquareTrade, what has worked and what has flopped?

Jason: As far as content, do you mean copywriting?

Jeff: It could be copy video or a campaign, in general.

Jason: I would say what has worked well is making stuff that’s useful to people. Like, the Breakability Campaign. And what’s kind of flopped or not worked as well is stuff that is more traditional advertising or old school advertising that was maybe  brand building without adding the useful piece to it. Or the education piece to it. We’ve done a fair amount of direct consumer advertising here, and it’s just such a complicated product and such a complicated industry that if you go with a campaign that’s pure brand, people don’t really understand what’s being advertised or why you’re better or the value. It’s forced us to be able to tell the story of the category and the product in a very real way- Like the Breakabilty Campaign- People can understand that. “Okay, I can see it. A phone is breaking and I get what you guys do. You protect phones and you do it in a better way.” What did a campaign, maybe five years ago with a big agency out of New York. We had spent like $1,000,000 on it, big tv campaign, and it was beautiful and funny and all that- award winning. But it didn’t really impact sales. And people were still kind of like “I still don’t quite get what you guys do.”

Matt: hmm

Jason: And the benefit of it. I would say the learning for me is maybe something different than working at a big brand, like a Target or a Yahoo, when you’re in a place like SquareTrade. You’ve got to do a lot more about education and  a lot more selling on the value of what we do than at another place where you’re just reminding people of the brand and that the brand is great.

Matt: Mmhmm That makes sense.

Jeff: And you have quite a staple of unique selling points, right?

Jason: Yeah we do. It’s a ton of different categories and each category and each product that we cover has its own staple of products and features. Whether it’s a phone and it’s getting out and fixing it as quickly as possible to a big tv where we’ll say “We’ll come out- We’ll send a guy out to repair your tv in one visit and if we don’t repair it in that one visit then we’ll buy you a new tv.” Service is different for each category so how do we communicate that in as quick of a way as possible? Especially because nobody goes to the store to buy a warranty, right? You go to buy a tv or a laptop or whatever you’re gonna do and then all of a sudden when you’re there, you’ve got to make this purchase decision right there. It’s from awareness to education to value to pulling the trigger all in a minute or two. After you’ve picked this other product that you’ve researched probably a lot. So, it’s a different way to sell.

Matt: And Jason, where are you actually educating those people? Are you driving them to the site or YouTube or how that working?

Jason: It depends on the store that we’re at.

Jeff: Mmhmm

Jason: 95% of our sales is at U.S. retailers. So, if it’s a store you know like a Target that’s not highly assisted more of the sale has to come through online research. Was somebody on their phone there. Or brochures. Merchandising versus, let’s say, if somebody goes into B&H Camera and Photo in New York. That’s a super highly assisted sale so most of education comes through an associate. Talking to people.

Jeff: Mmhmm.

Jason: In that case, we make sure that we’re really arming the associate with materials and everything that they need to talk to a customer.

Matt: Okay. Makes sense.

Jeff: And online are you integrated with the sales process? Like a B&H Photo?

Jason: So people can go online to SquareTrade.com and definitely check out the features and service and get education there. We’ve got a whole page dedicated to new plan holders and making sure that you know what you’re buying and when it starts and how to file a claim and all that. And then we do a lot on the service side to educate people too on “Hey, if you’re gonna file a claim, this is how it works.” We try to make it as easy a process as possible for people online because I think most people these days would prefer to do everything online, rather than have to pick up the phone and call somebody. So, we try to make it so you can do it in just a couple minutes online, and it just works.

Jeff: Alright, perfect.

Matt: Yeah.

Jeff: And yeah, I hate calling people. (laughs)

Matt: And have you integrated with online retailers?

Jason: We have.

Matt: Okay.

Jason: We have integrated with the online component of every retailer that we’re partners with.

Jeff: Okay.

Jason: Whether it’s Target.com or Walmart.com or all those in addition with eBay and other online retailers. All the way to NewEgg. Just very specific type of online retailers.

Jeff: So, eBay, you would even cover used products?

Jason: It’s really new products, mostly.

Jeff: Okay.

Jason: There’s just a couple of categories where we will do products that aren’t new. For example, we’ll protect any smartphone, new or old as long as it’s working. You can go on to SquareTrade.com and protect any smartphone. There’s a little test that you have to do. We just text you and then you reply to the text to make sure that your touch screen’s working.

Jeff: Yeah.

Matt: Oh that’s great. Yeah.

Jeff: Alright, well let’s jump to it. I would love to hear more. I was fascinated in just why you started with Modern Copywriter. Can you tell us a little story about that?

Jason: Sure.

Jeff: Yeah.

Jason: So, I started that Modern Copywriter in 2009 so right now it’s almost the 10 year anniversary.

Jeff: Oh, wow. Congratulations.

Jason: Thanks. Which is crazy to think about. But I started it as sort of a blog on the side. At the time I was at Target and I was the Creative Manager at Target and I had this open position for a Senior Copywriter there and just struggled. It was a great spot, I mean awesome company. In-house at Target’s a great team and struggled to find copywriter portfolios except through recruiters. It was just like “Where is the site online that just has features? A great copywriter portfolios site?” And, there’s a ton for designers, but where’s the copywriter one? And I thought “You know what? Maybe this is my blog idea. Maybe this is what I’ll do.” So I started posting copywriter portfolio sites, pulling them out of communication arts and some of my friends and asking people “Hey, is this okay if I post this up on a blog?” And people were pretty cool with it. And it took like three to six months and then school started picking up on it and using it for students. “Hey, this is, what a copywriter portfolio looks like.” And from there it really kind of took off. It’s been a great side project for me. And has kept me really connected with the copywriting community. And helped a lot of people get jobs. And helped students see what really good copywriter portfolio websites are and made me hate my own portfolio forever.

Jeff: (laughs)

Matt: Isn’t that with everybody in the creative industry? Your own site’s the worst. (laughs)

Jason: Yeah. Oh absolutely. Yeah.

Matt: Yeah.

Jeff: So what are you most proud of with the copywriting?

Jason: With that site? I’ve gotten a lot of really cool texts from people about getting work and stuff. But I’ve also gotten a lot of really cool texts from students saying “Hey, I have used the site a ton to figure out what kind of copywriter I want to be.” I know back when I was in college, I was in journalism school in Oregon and knew pretty quickly in college that I wanted to go into copywriting. I was lucky enough to find Janet Champ’s work. And Janet Champ was a big copywriter at Wieden and Kennedy in Portland. And she launched the women’s Nike stuff. She was writing poetry, you know? And magazine ads for Nike Women.

Jeff: Yeah, wow.

Jason: Just blew my mind. Just totally blew my mind.

Jeff: Wow.

Jason: So, for me, what I tried to tell copywriters who are just coming out or just starting to put their stuff together is find a copywriter out there who’s doing it and has a portfolio that blows you away and do that.

Matt: Mmhmm.

Jason: And call them and talk to them and say “How did you do it?” And “How did you get where you are? And how did you get that portfolio?” We have a pretty cool industry and people will talk to each other. So, I think that’s kind of what the site serves. Now mostly it’s just writers connect and inspire writers to do better work.

Matt: MMhmm.

Jason: And that’s probably what I’m most proud of.

Jeff: Have you ever thought about turning this into kind of more of a business? Or kind of a full time thing? Or is this just kind of a hobby thing for you? I mean, currently it is, but..

Jason: I have. Over the past 10 years, I’ve thought about a bunch of different ways to monetize it. I’ve had people suggest it. I’ve thought about making a book out of it. I’ve thought about, you know..

Jeff: Mmhmm.

Jason: Do I turn it into more of a recruiting site? You know because a lot of recruiters use it. There’s something about keeping it free and easy that feels more altruistic. An idea hasn’t come across my table yet that I’ve looked at or thought up and said “Yeah, that’s what I want to invest my time in.”

Jeff: mmhmm.

Jason: And it’s been a great way to connect with people and do all the things that I want. It’s served me very well.

Jeff: Yeah, yeah. When we spoke with you on the phone you mentioned you’ve hired some people off the site, right?

Jason: For sure. Yeah. Absolutely. I just hosted, Virginia Commonwealth brand center, just had their graduation week and they always send me, Ashley Summenall, who runs their outreach for BCU, every year sends me all their student portfolio sites. So I feature them for a week on the site and I see them before everybody else.

Jeff: (laughs) Okay.

Jason: It’s a benefit to me to be able to see who’s coming out and if I’ve got an open spot.

Jeff: Yeah.

Jason: Reach out to those people first. Or if I’ve got friends in San Francisco where I’m based who are looking, I can shoot portfolios their way, too.

Jeff: Mmhmm.

Matt: There is kind of the dribble monetization. Now I was circling back to the monetization part where you just offered a paid tier with other thing? I was just trying-

Jason: Oh, yeah.

Matt: Keeping it mostly free.

Jason: So it’s free to. The way it works is people email me their portfolio. And it could be our writers and directors also do work up there. I just opened it up like two years ago to anybody creative who wants to be on it. But there’s two ways that I’ve monetized it a little bit. One is I do paid job posts. So if agencies have an open copywriter position they want to post on the site, it’s like $150 and I’ll put that up there. And because I feel like that’s good for writers to get those jobs.

Jeff: Yep. Yep.

Jason: And then, the other thing is if a writer wants me to really look at their portfolio and analyze it and chat with them for an hour about their site and give them kind of an objective review of their site as someone who’s looked at thousands of copywriter sites over the past 10 years, I’ll do that also for $150. And the only reason I charge for that, honestly, is because so many people were asking me to review their site, and I’ve got a pretty busy day job. So, I just charge to make sure that people are serious. (laughs)

Matt: (laughs) Okay.

Jason: Actually want to spend the time- They want me to invest the time in it and they’re gonna invest the time, too.

Matt: Yeah, makes sense.

Jeff: And that could be incredibly helpful for someone starting their career or just looking to job seek. Having somebody say “Yeah, you’re way too in the weeds on it. And from my perspective it looks like your portfolio needs a little bit of this help, which could mean the difference between a career and still seeking for a job.”

Jason: Yeah I get. Most of the people who ask me to do that are people who’ve been in the industry for a while. But maybe they haven’t done a job search in a couple of years and they haven’t revamped their site in a while. And they’ve got the work that they got, but they want to know the best way to present it. And that’s what I can kind of help with and say, “Listen, maybe you should move to SquareSpace or integrate Venmo with it or your nav is kind of tough to click back and forth. Most people looking at your site, the first gatekeepers, they’re gonna take about 60 seconds to click through your site and your site’s kinda hard to navigate. Or you’re missing this component, your bio could use a little help from here. That’s kinda the advice I try to give. It’s more from an objective standpoint as someone who’s looked at a lot of copywriter portfolio websites. Rather than a subjective “Hey, I’m just a creative director and I like your work or don’t like your work.” Because I think most people, I know plenty of people who can do that..

Jeff: Right.

Jason: But maybe don’t get the objective. “Hey your site is kind of not working great because of this and this.”

Matt: Yeah, the presentation more than the content.

Jason: Totally. Exactly. Yeah.

Matt: Yep.

Jeff: What a great service. I mean $150 is pretty much free. I think that you’re helping a lot of people doing that for them.

Jason: It’s fun. I’ve been doing it for 10 years so I obviously enjoy it, but it keeps me fresh too looking. I get to look at so many copywriter portfolio sites and, as a writer myself, it’s a blast. I get to see a lot of work through Modern Copywriter that I would never see.

Matt: Yeah.

Jason:  And then connect with a lot of writers that I wouldn’t get to connect with otherwise. Especially being in-house. I’ve been at SquareTrade now for almost 7 years, so I’m not in and amongst the agency community. And Modern Copywriter is kind of my way to do that.

Matt: Yeah that’s great.

Jason: Yeah, it’s cool.

Matt: Yeah.

Jeff: Well awesome Jason. We are just about our half hour mark. Any plugs? Or would you like to make any final comments to our audience?

Jason: Yeah, this has been a lot of fun. You guys are great and it’s fun talking about copywriting and Modern Copywriter. So, I really appreciate you guys asking me to be on.

Jeff: Great well yeah.

Matt: Of course. Thank you so much for being on.

Jeff: Yeah, thank you so much and we’ll definitely be listing links to the very things that we spoke about in the show notes. It was great talking with you Jason.

Matt: Yeah and copywriters out there. Contact Jason and have him view your portfolio. That is such a huge help, and if you’re looking for a job or just looking to see what opportunities are out there, you couldn’t ask for more than a little bit of Jason’s time and to help you present your stuff.

Jeff: Great job, Jason.

Jason: Yeah, anybody who wants to get their portfolio featured on Modern Copywriter, again it’s free. Just send your link to Jason@ModernCopywriter.com and I’ll get you in the queue. Thanks guys.

Jeff: Awesome. Yeah, thanks so much Jason.

Matt: Thanks a lot Jason.

Jason: Alright. Bye.

Jeff: Alright, have a great day. Bye.

Speaker: For show notes and information on DigitalRage.fm follow us on Twitter and Instagram at DigitalRageFm and please, give us a rate and review. We sincerely appreciate it.

Show Links

Host, Web Designer, SEO
About the Author
Jeff Byer has been designing identities and building websites since 1995. He is the CEO and co-founder of Print Fellas LLC, and the President at Byer Company, a division of Jeff Byer Inc, a web design company in Los Angeles. Jeff has a Bachelor of Arts Degree from the Annenberg School for Communication at the University of Southern California. He is a certified Project Manager by Franklin-Covey and has qualifications in Photoshop, Illustrator, HTML, PHP, JavaScript, MySQL, SEO, Bing Ads, and Google Ads. Jeff Byer is a co-author on 5 US Patents related to content management systems he has created on the internet.

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