Skip to content

Boardriders’ Milano gives FLOW audience advice for navigating shifting retail landscape

Join our mailing list

Signifyd regularly publishes free reports packed with business insights, commerce trends and data from our massive Commerce Network. We’ll only email when we have something meaningful to share, no more than once per week. And of course you can unsubscribe any time.

Listening to Anthony Milano share the wisdom he’s collected during a career in retail is a reminder that while getting retail right is sometimes simple, it’s never easy.

Consider the innovation Milano helped spearhead when he was at Hugo Boss, where he ultimately served as vice president of ecommerce. The conversion rate online was nothing like the rate in-store, which should surprise no one. But wasn’t there a way to better leverage the online experience?

Milano and his team realized there were challenges to buying expensive suits online. You can’t try it on. No one is there to explain the cut and the features. So, Hugo Boss came up with a way for online shoppers to make an in-store appointment with an expert associate.

“When they showed up,” Milano said, “there was champagne waiting.” And not only that but a selection of relevant garments would be ready for the customer, the result of information gathered through live chat with the customer.

“So we were able to, from an omnichannel perspective, use all these touch points to the consumer, and create some really awesome customer journeys,” he said.

Awesome for the customer and awesome for Hugo Boss because the appointment visits resulted in average order values that were 40 percent higher than other in-store purchases.

Milano, now Boardriders’ vice president of ecommerce for the Americas, offered an advanced class on omnichannel retail and navigating a career in the retail industry at Signifyd’s FLOW Los Angeles, a gathering of Southern California retail professionals looking to share challenges, solutions and to help each other navigate the rapidly shifting world of retail and ecommerce.

And while Milano covered a lot of ground during a fireside chat with Indy Guha, Signifyd’s vice president of growth marketing, he kept returning to a theme: By knowing and understanding your customers, you can serve them in ways that will delight them and keep them coming back. And, of course, delighting customers is channel agnostic. You need to delight them where they want to be when they want to be there.

Sure, it’s great to delight them with appointments online and champagne in the store. But there are other ways to build a great experience — more basic ways. Think about loyalty and how to build it.

Loyalty programs have become a go-to, but are they really the answer? Milano said that at times such programs risk becoming like discounts and promotions — strategies that bring a short-term bump, but don’t necessarily win customers over for the long haul.

Say a loyalty program offers a discount on a customer’s birthday, Milano said.  Nice thought, but does it build lasting bonds?

“Am I loyal now because of your program?” Milano asked. “Or am I loyal because I know you give good service; you have products I like; I like your fit?”

“Can you drive long-term value by just offering good service, making sure your packages get out within a day, making sure that your picking up the phone if they call customer service, in 20 seconds?” He continued.

His answer, of course, was yes.

At a time when retailers and consumers both are raising their standards for what makes for a good customer experience, the bar is only going to be raised higher. Already new, upstart brands are bursting onto the scene and becoming household names, seemingly overnight, by offering high-quality products, a compelling story and a clear way of communicating with consumers.

“You’re seeing some brands come literally out of the woodwork,” Milano said. “They’re starting with a loyal audience, a fan base, before some of them even sell any product. They’re creating amazing content that has some sort of driver or message. They stand for something. Or they’re finding something super niche.”

He pointed to brands such as Glossier, Ashley Stewart and ThirdLove, a company that in 2018 donated $10 million worth of bras to women in need. Increasingly, contributing to social good is part of the experience that consumers are looking for.

“They are brands that stand for something. They’re standing for a message. Whatever it is, it’s touching people’s heartstrings and really getting them involved emotionally. And then I think they’re creating the audience, getting the following and then they are commercializing off of that in a more authentic way.”

Milano also acknowledged what many in the room knew: Building a customer-facing strategy is only part of the battle for those who run digital operations in a commerce company. Ecommerce leaders at omnichannel retailers also must press their case with executives who have responsibility for both the brick-and-mortar and the digital sides of the business.

The way to make that case, of course, is by having the numbers to prove it. So, Milano said, think of ways to establish the success of an idea without necessarily having to launch it full-scale.

“Show me the money,” he said. “If it works, it’s going to prove out. Whether it’s an A/B test that you can run or it’s a new vendor that you can do a pilot program with, any way you can show results prior to doing the investment or carving out the time, energy and approach to get it kicked off, I think is the best approach.”

What was clear, listening to Milano, was that retail has a lot going for it. The industry is evolving rapidly and true leaders are emerging — leaders who are not afraid to try new ways to engage with customers, while seeing to it that retail is as meaningful to them as it is to those who practice the profession.

Photo by Gregory Mancuso Photography for Signifyd


Mike Cassidy

Mike Cassidy

Mike is the head of storytelling at Signifyd. A former journalist and a retail geek, he covers ecommerce and the way technology is transforming digital commerce. Contact him at