It has been tough going for bricks-and-mortar retailers.
Commercial rentals are rising, it is difficult to hire workers, and consumers are increasingly shopping online.
Still, technology might just come to the rescue in helping shop owners grapple with the islandwide push towards improving productivity.
Traditionally, these businesses have been solely reliant on staff dealing with customers to make their sales.
But retailers are increasingly turning to data analytics to tailor offerings to the preferences of individual customers.
This includes making use of data to target discounts at specific customer segments and offering shoppers customised perks.
Luxury watch retailer Aptimos started keeping track of customer data using a business solution provided by tech firm Capillary last year.
"The database will help us keep track of customers who always buy a certain brand of watches, for example, so that we can let them know when relevant promotions are coming up," said Ms Edna Ng, the company's director.
"We are also looking into ways of using the database to reward customers for their loyalty."
Using big data to target advertising at specific groups helps retailers improve the effectiveness of their marketing efforts by "driving the right consumers to your store", said Mr Aaron Boey, a member of the National Productivity and Continuing Education Council.
"A critical retail performance indicator is 'conversion' - of the people who walk into the store, how many actually end up buying," said Mr Boey.
He is also the former executive vice-president and president of commercial operations for Asia-Pacific at Levi Strauss and Co.
Retailers are starting to use data not just on the shop floor, but also to manage backend functions such as manpower allocation and inventory management.
Mr Warren Teh, the director of operations at the E-Lush Retail Group, said the company has been keeping track of "power hours" - a store's busiest periods - and plans to bump up the number of part-time staff on duty at those times.
The company runs the iStudio chain of Apple retail stores.
"Part-timers may not have as much product knowledge, but they can attend to customers and prevent them from feeling left out while senior staff focus on more complicated cases," said Mr Teh.
"We have two main types of customers - people who already know what they want and people who come in to browse... Customer service is important because people may not buy immediately, but will come back later," he added.
Efforts such as these have helped the retail sector achieve nominal productivity growth of about 3 to 4 per cent every year since 2010.
However, productivity levels in the sector continue to lag behind that of other service sectors in Singapore.
The value added per worker in the retail sector is about $44,000 - below the overall services sector's average of $97,000.
Mr Simon Ho, the deputy chief executive of CapitaMalls Asia, said the labour crunch is affecting the company's retail tenants to a lesser extent than those in the food and beverage industry, "which is a lot more labour-intensive".
Still, the retail sector has been flagged by the Singapore Business Federation as one that requires more targeted assistance in the upcoming Budget - for instance, in improving its image to attract Singaporean workers.
The association also recommended that on-the-job training support schemes for workers in the sector be enhanced.
Retail is a sector that is "more similar globally than some other sectors", said Mr Boey.
Technological advances in retailing that have been implemented elsewhere can therefore be easily brought into Singapore - for instance, hand-held devices that can reduce crowding at cashier counters or real-time portals that allow companies to push out staff training modules through their point-of-sale systems.
"There is some responsibility on the part of bigger companies in the sector to be more proactive in testing out these things... There will then be scope for a trickle-down effect through the rest of the sector," he added.
For most retailers, however, costs remain a top priority.
Mr Gary Khoo, the managing director of eyewear retailer Spectacle Hut, said the company has been "trying not to increase prices, but eventually will have no choice but to do so".
It has invested in automating its inventory management and point-of-sale systems to reduce manpower, but "rentals in the malls keep increasing and wages keep going up...
"At the end of the day, consumers are the ones who are going to have to pay more".