How to Get Started with Shipping for Your Online Store with Robert Gilbreath


In today’s podcast, we are venturing into what many find to be the second most complex part of running an online store with physical products, and that is shipping. As with taxes, it’s a maze of variables and choices that can often bog you down.

And to help you to get a better grip on planning our shipping, we invited Robert Gilbreath, VP of Marketing & Partnerships at ShipStation. Robert provides some great guidelines that not only help you get started but also to get you thinking on preparation for scaling as your product inventory grows.

We chatted about:

  • The first two important steps to make once you know the product that you need to ship
  • How to navigate the maze of shipping options
  • Some of the major challenges store owners face when working through the shipping process
  • What products can be a challenge to ship
  • Robert’s four points to consider when planning your shipping
  • When shipping is no longer a DIY part of your business

Thanks to Our Podcast Sponsor: Bluehost


Bob Dunn: Hey, everyone. Bob Dunn here, known as BobWP on the web. In today’s show we are going to touch on a subject that many online retailers need to know. We’ve talked about taxes, which is huge and have yet to touch on the subject of shipping.

Now we know that taxes make a very broad and complicated topic when it comes to online sales. Possibly it’s the most complicated, but shipping kind of falls right behind that because there are certain challenges, especially when you’re looking at a store with a lot of products shipped across the world. Even local shipping has to be done right. So if you’re someone just starting out as an online retailer or looking to increase your product line, today I’ve asked Robert Gilbreath, V.P. of marketing and partnerships at ShipStation, to join us. Hey Robert, welcome to the show.

Robert Gilbreath: Hey, thanks for having me.

Bob: My pleasure. Now Robert, before we really get into the questions, what I’d love to do is have you tell us a little bit about yourself and what ShipStation does.

Meet Robert Gilbreath, VP of Marketing & Partnerships at ShipStation

Robert: Sure thing. I feel like I have a pretty interesting story because before I joined the team here at ShipStation, I was an eCommerce retailer for most of my career. I started selling on eBay in the mid- 90s, a year or so after eBay launched. My dad and I started selling auto parts on eBay.

That was sort of my toe in the water and I got hooked really quick. I learned a lot about online marketing and search engine optimization originally by learning how to be a good seller on ebay. I had done some other sites outside of the auto parts world and then became a thought leader and an executive at several rather large online retailers. Most recently, before I joined ShipStation, I was running eCommerce for which is an internet retailer, top 500 reseller of calendars Yes, people still buy big paper calendar—lots of them.

Bob: My wife does. She loves hers. She has to have that one that’s on her desk.

Robert: Yeah. The loyalty and affinity to some calendars is pretty amazing. But, you know, so I spent most of my career being a retailer and the opportunity came to join a ShipStation and I literally have been, any size customer that ShipStation’s going to have whether it’s mom-and-pop like my dad and I selling a few auto parts on e-bay, all the way up to guys who ship a quarter million things a week. So while while shipping isn’t something that’s super sexy. No one gets into eCommerce or retail because they’re like, oh geez, Bob let’s be really good shippers, right? People have cool products. They have cool ideas. Then you figure out a niche where they can do some cool things online. And then shipping and then it’s like the “oh no” moment happens. And then shipping becomes so important. So whether or not it’s a sexy topic, it’s just something like you you said earlier, accounting is really tough and I would argue, next in line on the on the hardness scale for almost any size online retailer, is shipping.

What are the first things an online retailer should consider when looking at shipping their products?

Bob: It’s definitely the same way with taxes. When I was doing taxes on a podcast series, it was like, OK, this isn’t a sexy subject but hey, it’s something you need to know and whether you do it yourself or have somebody else do it, knowing all the ins and outs is what’s going to make or break you. Okay, let’s start with a big picture question. When you know that the product you are shipping, you already have in place, what are the very first things an online retailer should consider when they are starting to look at shipping that particular product?

Robert: Yeah, super basic are things like what kind of packaging they’re going to use. Is this something that can go in a padded envelope versus a box, depending on their skew variety? You know, in the breadth of product you need to understand the supply side of what you’re doing. So we’re going to talk through some ideas on how to be super efficient in what we’re shipping. But if you don’t have the right packaging, the right supplies, you hit a roadblock. So I really try to tell people to think about the packaging side of what they’re doing and figure that out. Also maybe even a little bit of pre-shipping is how they’re going to store their items before they’re actually sold. Are they going to have space in their garage? You know the startup type of thing: thinking about how those things are organized. Sometimes it’s little nuances of things that if you can get those out of the way early, you don’t have to worry about them anymore. So I think that would be my advice as far as the initial things to think about.

How do we navigate the maze of options for shipping products?

Bob: Now there’s a lot of choices and this probably gets into a bit more of the nitty gritty on how you can ship your products. So, there’s all the different shipping companies: USPS and on and on and on. How does somebody get themselves through that maze successfully? What do you recommend as far as guidelines to help them start deciding who are they going to have ship their products?

Robert: Yeah, you know, I love the analogy of a maze because it is a maze. If you think about it this way, the way to solve a maze is to understand what kind of maze you’re in, right?

So I really suggest just some fairly simple education. Well,I’ll back up to the other question and say, understand your product. Know what kind of packaging you’re going to need. Maybe you’re shipping in just the U.S. or maybe you’re going fully international. Let’s assume you know all those things already. Then it’s time for some education. You know, obviously, that all the carriers want your business. You know they’re all providing some degrees, there’s a parallel of product offerings.

And then if you have some nuances, that’s when you have to educate yourself. Do you have a certain type of product that needs a certain handling or needs to be managed a certain way? So again a high level of understanding of the differences in the carriers. And then next would be thinking about things like, let’s say you’re doing free shipping. Free shipping is almost a must these days for most most retailers, right? So, understanding the cost. Let’s say you educated yourself. Maybe you’ve picked a few carriers, understanding the cost of those shipments. Is free shipping something you can even do? Do you have to raise the price of your product to make it work? Do you have to have some products that don’t have it? You need to do free shipping with minimum understanding what those shipping costs are and having it as part of that education as super important.

What are some other challenges store owners face when working through the shipping process?

Bob: Now with those two questions in mind I’m sure you probably have a long list, but let’s just go through a few of the other challenges that store owners will confront when working through the shipping process of their products.

Robert: You know what, Bob, I could probably give you one principle that I think folks need to be concerned with and it’s a good problem to have but, it’s the problem of how do I scale and grow my operations. So, yes, we want a lot of sales, but what’s going to happen if we get a lot of them and something that my team put into practice with the last retailer was this idea of almost doing a practice drill. It’s almost a fire drill of ‘what if’?. And the director of fulfillment there at that company would literally time the different steps of the fulfillment process. So he knew down to the seconds how long something took. So he knew, for example, how many people needed to hire for a season, depending on how many sales he had.

And so with that same idea, you don’t have to be a multimillion- dollar retailer to practice, right? Even if you only shipped three things a week, you should be able to know how long it takes you to ship one thing and then you don’t have to worry if the best thing happens, which that scaling that happens when your sales go up. I really think of people optimizing their shipping as sort of this admin flow. And like accounting and taxes, it’s it’s hard, but you can figure it out. There are tools out there to help you and then you don’t have to worry about it anymore. So if you’re a little bit of a road bump figuring those things out and then people can get back to their businesses.

Can you give us a few examples of products that come with specific shipping challenges?

Bob: I’m sure there are tons of examples, but can you give us a few products that come with specific challenges when it involves shipping them and maybe even offer what people should think about as far as those particular challenges?

Robert: I think things like food and other perishable items come with their own challenges, whether it’s the need to use dry ice or special packaging. We have one customer here at ShipStation that does handmade candies. She ships them out in old fashioned mason jars. She doesn’t really have a perishability issue, but she had to tweak a little bit to find the right-sized box that could hold the jar from top to bottom. And then she had to figure and out how to wrap it so that when the customer opened it, the wrapping looks right and, most importantly, the jars aren’t broken. So perishables obviously.

And laws are changing around alcohol shipping. As with perishables, that presents some interesting challenges. Kind of go back to previous question of how to become educated about the carriers that offer certain services around perishables, around food, around alcohol. And those can be learned quickly and can be applied to the business. I guess the other one to keep in mind is knowing that high-value items are fragile items. Folks need to educate themselves on insurance and whether they need to pay extra insurance. Are they in a high-fraud situation, where maybe the countries that they’re decided to ship you are high fraud? So they need to think about the insurance side of what they’re shipping out to.

Bob: It sounds like it’s very complicated with laws as far as the alcohol. I was just thinking of that because a little while back I got a basket from a vendor, a thank-you, and it had some wine in it and it was wonderful, it had chocolates and I had a great time. But I was thinking, wow, I didn’t have to show ID. Did the person on the other end have to say I’m sending this to somebody of legal age? The cross-border thing and the laws are so different from state to state or country to country. It just seems like it’s a mind boggling thing.

Robert: Yeah. I would say it’s probably like the third: taxes, shipping, and then shipping alcohol. It’s state by state and then it’s spirit by spirit, where some states are fairly open as far as wine and some are not as open to whiskeys and things like that. Obviously, there’s a bit of a hazard to transporting high-alcohol content. The liquids pose some challenges. You’ve been, we’ve been in this space a long time, and I’m sure you know stories of the’s of the world and folks that turn family liquor businesses into online sensations because they were early and they were able to figure out all the little niche nuances of that business. So while there’s challenges there, I think it’s still some pretty fertile ground for folks.

Bob: So there’s not a UPS guy who’s going to start saying, “Hey, can I see your ID please?”

Robert: I thought for a second you were going to suggest the UPS drivers were hitting the boxes a little early but you weren’t going to say that.

Bob: Really. Oh. This box seems to have been opened. Mmm interesting. Boy, this wine is a little watered down.

Robert: OK. Yes, if you’re listening, we’re joking. Just joking.

Anything else around shipping?

Bob: OK. Is there anything else around shipping? I’d kind of like to leave it open at this point, in case you have some other insights or tips you want to share. Because we’ve touched on all of this. But yeah, just take the floor and give us some more great insights.

Robert: Yeah and it may be an opportunity for another chat in the future, Bob. When we’re talking with users and we’re thinking about how we’ve built ShipStation, as well as a piece of software that online retailers are using, we think of four principles. I’ll touch just super briefly on each of them.

But it’s thinking about being seamless. How many different pieces of technology are you having to use? Think about that. You can reduce that number.

It’s about being efficient. How many times are you having to touch the product before it goes from the point that it’s on the shelf or in your spare bedroom in a box to the point that the carrier picks it up? Think about that and see where you can minimize those.

It’s about being organized. The virtual world of your software needs a physical world. It can be as simple as the desk you’re using to shift from the table in a garage to a table in a warehouse. But thinking about how the technology pieces, the software, the hardware and the physical environment all come together.

And then finally the last principle is about being scalable. Because scalable is such a cliche, we like to use the term, the ability to ‘welcome growth.’ So it doesn’t matter that you have 10 orders today and you still only get one a day? Or does it matter that you get 1000 today versus 10? You should be able to welcome that growth even if Oprah picks you as her favorite thing or you are on Good Morning America or something like that. Bring it on. The attitude should be, bring on the orders here. I’m ready to grow. So, yeah.

At what point should I think about moving from do-it-yourself to using a shipping partner?

Bob: Now I’m going to throw one more thing in here. Let’s say I have three products and I’ve got it all down. Maybe I’m using eCommerce and I’ve set everything up in WooCommerce and I’m packing stuff and I’m shipping stuff

and everything’s kind of cruising long pretty good that way. With ShipStation you offer specific services. Where do I decide? At what point do you go along where you’re shipping and you say, well, this has been fun but I’m getting really tired of this. I need somebody to help me. Is there a certain time frame, or a certain point in time, I should say, from your experience working with clients that people finally say, maybe this isn’t a do-it-yourself type of job?

Robert: Yeah you know there’s not a single point because it’s super personal. I’ll use myself for an example. I recently relaunched a personal eCommerce site, mostly because I wanted to get back into playing with all the various tools, you know, Woo, Shopify, you name it. I want to play with them again. And so I’m doing handmade articles, so they are 100 percent custom for that order. I’m doing hand stamping all leather right now. There’s no way I would ever outsource that, at least not in its current form. Because part of the coolness of what I’m doing is that people know they’re handmade by me. I’m sharing pictures of the process and everything. So I would never be in a situation where I’m going to outsource that because it’s one-offs and very low volume. If it starts to grow to a point where you become uncomfortable with it, right? Let’s say it’s a volume issue or a warehouse issue. Then, at that point, somebody might decide maybe it is a good time to think of third party fulfillment house. Maybe it’s more cost-effective for me.

Let’s say I’m selling shirts and they’re custom made. Maybe it’s it’s more economical for me to ship those to a holding warehouse that can do drop shipping for me, versus bringing them all into my own warehouse or office. So there’s not necessarily a one inflection point. It’s fairly personal and, you know, depends on what the individuals are selling.

Where can we find Robert Gilbreath on the web?

Bob: Well, I think this gives us at least a good start in the topic of shipping. And hopefully in the future, we’ll be able to get in deeper into specific areas. Now I’d like you to tell us, besides, which I’m hoping everybody will check out, where else can they find you on the web?

Robert: The ShipStation blog is a good place to find me pontificating on not only shipping best practices but also best practices around marketing for your eCommerce site. And you we just finished up a series on photography for your site. So the ShipStation blog is the best place to learn more about what we’re up to.

Bob: Cool. Well excellent. That’s another wrap. And I would like to thank you, Robert, for taking the time to be on our show.I’m hoping to talk to you again here in the near future.

Robert: Sure thing. I’m really looking forward to it.

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