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How Retail Store Employees Should Upskill Today

The nature of working in retail is changing at pace as the purpose of stores continues to evolve. BoF Careers examines how in-store employees can hone and develop their skill sets for success in retail or its adjacent industries, sharing expertise from retail leaders and fashion executives who began their careers on the shop floor.
Two individuals working in a store are looking at a piece of clothing in a retail store. They stand near a clothing rack and a table with various items.
Retail is the largest private-sector employer in the US, supporting 42 million jobs. (Pexels)

The Insider Advice series offers advice from leading fashion professionals, HR leaders and academics, to answer topical careers questions for today’s fashion employees and help inform and guide you in your career. Discover the latest job opportunities with 2,000 roles on BoF Careers today.

Retail jobs have also historically offered a meaningful first foot in the industry door — the National Retail Federation (NRF) in the US estimates that 32 percent of Americans experience their first jobs in retail. It is also the largest private-sector employer in the country, supporting 42 million jobs.

But the retail landscape has changed dramatically in recent years, especially since the outbreak of Covid-19 when lockdowns and store closures forced a reset on the purpose of physical retail. Enticing consumers back in-store and broadening the purpose of a brick-and-mortar location in an age of digital and social commerce has seen the explosion of experiential retail and in-store services.

Today, retail teams might assist in product fulfilment, data gathering or omnichannel clienteling and social media activations. “Store associate” roles have subsequently been rebranded to better reflect store staff’s shifting responsibilities — retailers now recruit for client advisors or consultants, brand or community ambassadors. For many working in stores, adapting to the evolving retail landscape and staying on top of the necessary skill sets can feel challenging.


To understand how to upskill as a store employee, to progress in a retail role or demonstrate transferable skills for creative or corporate roles in adjacent industries, BoF Careers gathers advice from retail thought leaders and fashion executives who began their careers on the shop floor.

Focus on Skill Sets for the Career You Want

Job responsibilities on the shop floor cover a broad range of tasks, offering the chance to learn hard skills like handling stock, SKUs and seasonal buys, merchandising and in-store marketing. Employees must also develop soft skills through store team collaboration, client communication and problem-solving to meet consumer requests and retain the sale.

As a result, retail workers have the opportunity to develop a wide skill set — and should consider how these will translate into career opportunities in retail or its adjacent fields — fashion, beauty or luxury.

“If you want to design clothes, if you want to be a merchant, if you want to be a planner, working in the store is critically important because you [...] are with the customer every single day. You are understanding the operations of getting a shirt or trousers or shoes to the [shop] floor, how it looks [in-store] and how it needs to be restocked, how customers engage with it,” says Adam Lukoskie, executive director at the NRF — the educational branch of the NRF in the US.

One example of a leading fashion professional who leveraged her first role in retail for future success is Linda Ayepe, head of womenswear buying at Harvey Nichols. Ayepe worked at a surf shop while growing up in Cornwall, a remote county in the UK. She credits this job as formative in providing her “first insight into how buying works.”

Retail [is] a challenging environment, but I highly recommend it [as a point of entry] because then you get this exposure to the brand in a way that you do not normally as a customer.

Those looking to develop and hone skill sets should focus their attention on upskilling in a select few areas of their job spec based on their career aspirations. This focus will enable a greater quality in development rather than trying to achieve mere quantity in it, and ensure you still deliver in the core competencies required for the job at hand.

For those uncertain of their career aspirations, the breadth of responsibilities for a store role can also offer an introductory insight into the areas in which you are interested or excel.

“Think about [...] what you’re really good at and what your interests are. If you really want to be a merchant, then it’s about — how do you make money? How do you manage the finances if, on the other hand [...] you like procedures, operations, that sort of thing,” Craig Rowley, senior client partner at business consultancy Korn Ferry, told BoF.


Should you need further inspiration in how to identify which skills will be most valuable to your career aspirations, you can research professionals in roles you aspire to, who started in retail as well. On platforms like LinkedIn and other professional networking spaces online, individuals often detail skill sets learned and acquired, which can key insight on where to start. You might also try reaching out to ask them directly how their first job helped them achieve their success.

As Adam Baidawi, global editorial director at GQ, advised in his Building a Career in Fashion on Linkedin, you should think about how you can “work backwards from your ideal and take the first step towards that goal. How can you effectively reach out to people who could be good allies? [...] if you’re not quite sure where to start, start at the finish line and work your way back through the race to figure out what the next step is.”

Identify Learning Opportunities With Your Manager

Your store manager and colleagues can be a useful resource and support network to help you upskill in your areas of interest. For example, where one colleague might not enjoy showing consumers how to use the latest technology in-store, you might want to focus your attention on it; while another colleague might have no interest in assisting in social media posts, you might want to pursue a career in social or marketing.

You should have a conversation with your manager about what opportunities there might be to develop, such as volunteering at in-store events or running experiential activations. Showcasing a proactive approach to your manager will also assist in chances of internal progression and opportunities shared.

“It’s very rare that internal promotions are going to happen without a strong endorsement from your current supervisor,” says Lukoskie. “So, how do you help your boss be successful? And, how do you stand out with your current boss?”

Meanwhile, you can also ask if there are any upskilling and training opportunities through headquarters. Increasingly, retailers and fashion brands are identifying potential recruits from their shop floors, looking at the talent pool already in-house, who will be familiar with and well-trained in the product and brand. British retailer Selfridges, for example, only offers their sought-after internships to internal talent from their store network.

Expand Your Product and Brand Knowledge-Base

Today, consumers are often heavily informed on products and brands. From the fabrics used to the runway styling to the supply chain journey, information is constantly at their fingertips through digital resources and social posts. As a result, store staff need to have a firm and thorough understanding of the products and brands they are selling — if not to rival, at least to match their clients’ knowledge base.

Take the time to educate yourself on the brand for which you work. This process should include you attending and actively participating in training days. However, there are plenty of other ways in which you can upskill in your own time.


If you want to design clothes, if you want to be a merchant, if you want to be a planner, working in the store is critically important because you [...] are with the customer every single day.

For one, research the products online and across multiple platforms — you want to understand the items themselves, the narrative and language brands use to describe the product, as well as the way customers are reacting to it online.

“I worked as a retail manager at the Ralph Lauren Mansion at Madison and 72nd — that was my first real fashion job. [...] I devoured the storytelling that Ralph Lauren had to offer of the product and the vision,” shared fashion merchandising executive Kiera Ganann, who went on to become the VP of sales and merchandising at the American luxury business.

Your research should encompass comparing stock across different multi-brand websites, which will help you understand which pieces are bestsellers and which have not performed as well, and how that measures up with in-store consumer behaviour. You should also stay up-to-date with marketing campaigns and brand ambassadors — to grasp the holistic vision of the brand and the role the store plays in that vision.

“Retail [is] a challenging environment, but I highly recommend it [as a point of entry] because then you get this exposure to the brand in a way that you do not normally as a customer,” Amiyra Perkins, senior lead of creative strategy at Pinterest, previously told BoF.

Engage With the Next-Gen Technologies Shaping Retail and Fashion

In a bid to engage and entice consumers in-store, many retailers are funnelling resources into the latest technological advancements for their store networks.

Some tech offers an entertainment value, like Coach and Tommy Hilfiger’s augmented reality mirrors in store windows, allowing for playful virtual try-ons. Some tech is more about efficiency, like radio-frequency identification (RFID) tags used by Zara, Uniqlo and American Eagle for an improved self-checkout process and better inventory tracking. Other tech tracks consumer behaviour patterns, collecting data on which SKUs were the most sold, searched for and requested in-store.

First and foremost, working in an environment with these technologically advanced tools gives store associates an insight into the latest retail tech developments — and how to use them. As a consumer, you engage with these tools infrequently, if at all; as employees, you can develop the hard skills required to use the devices or software daily.

One technology that is fast being integrated into every level of the value chain, including stores, is generative artificial intelligence, or gen AI. In fact, BoF and McKinsey’s State of Fashion 2024 report found that 62 percent of fashion businesses already use gen AI in the workplace. However, just 5 percent of surveyed executives said they are ready to make best use of the technology, suggesting a talent gap that businesses will increasingly need to fill.

Retail teams have an opportunity to immerse themselves in the technological tools like AI that will be eventually prevalent in every workplace. What’s more, by being the first to engage with new programmes or attending training from corporate to feedback to your team, you can position yourself as the “go-to” individual for queries surrounding new software.

It’s very rare that internal promotions are going to happen without a strong endorsement from your current supervisor. So, how do you help your boss be successful?

Store teams are also at the forefront of consumer data collection. While a lot of this data and its insights are directly funnelled back to headquarters, associates have the most direct, personal engagement with the end-consumer.

In a client-facing role, you can gather anecdotal insights into what customers are saying about the product, brand or omnichannel service. You can use this information to your advantage while engaging other customers and share it with your manager and team. Lukoskie adds that retail employees can witness first-hand “the unique opportunities and new challenges that a corporate policy might have,” as they will see it play out each day.

You should consider the opportunity this presents in developing soft skills if you struggle with the social aspect of speaking to consumers. Certain digital tools used by store associates today will share personal data on which consumer has just walked through the door, offering the associate information as simple as their name to ease into the social interaction while providing an exemplary and personalised service.

“You could walk into the store, my phone lights up because we’ve got your telephone number and it says, ‘here comes X and they like Y and Z’ — so I can greet you by name, particularly if you shop the store regularly,” says Rowley, who was previously director at US retailer Macy’s and is now a thought leader in the HR retail space.

Practise Your Leadership and Managerial Skills

Retail offers a unique opportunity to develop managerial and leadership skills early on in your career as successful sales associates can step into store manager roles.

This progression provides the chance to learn skills like managing and communicating with a team as well as taking on the responsibility for the store performance and sell-through. This often requires taking initiative and acting quickly when needed.

“If it’s 75-80°F [25°C] and you’re walking down the street and you look at the [store] window and see beautiful cashmere sweaters, you’re probably not going to go in to buy one. [...] You have to be sensitive to all these things about what’s going to meet the customer’s needs,” adds Rowley.

With the career aspiration of becoming a general manager one day, Jeffery Fowler, CEO of watch media company and retailer Hodinkee, pivoted from his career in management consultancy to retail. Fowler previously told BoF that he wanted to “dabble in a lot of areas of a business without necessarily having to pick a lane and pigeonholing [himself] effectively in that one function. I think retail, uniquely, in the earlier stages of your career, gives you an opportunity to do that,” he continued.

Indeed, sometimes, retail is also exactly where a fashion business or retailer would want you to start: “When I thought about joining Louis Vuitton, I assumed I [would] slide into a corporate role, but they hire folks with the type of background I had and throw them into the deep-end in retail and say, ‘Here’s a store, there’s a position in the management of this store. Go and learn the business,’” said Fowler.

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