Paying close attention to executive appointments in corporate leadership beats reading tea leaves every time. Who gets picked — their past experience, their personalities, their reputations — says volumes about a retailer's hopes, wishes, and dreams.

In 2014, the retail sector is laden with a smorgasbord of uncertainties, from the future of brick-and-mortar stores and the possibilities of e-commerce to the realities of fulfillment and payment systems. The six executives we looked at below each have a lot on their plate. They were brought in to take on fundamental challenges at highly idiosyncratic companies — in some cases with drastic need for financial turnaround and/or lifesaving measures to the brand. With so much at stake in this sector, it will be interesting and informative to see how these six — five men and one woman, five CEOs and one chief of retail — do in their new positions.

Angela Ahrendts —​ Chief of Retail, Apple

Ahrendts is credited with performing something of a magic trick at Burberry: Boosting the brand’s profile as chic and trendy while maintaining its image as a longstanding classic. Ahrendts is from Indiana; her fellow alum at Ball State University is uber-goof David Letterman. But Ahrendts, 53, brings to Apple as chief of retail, a position that has gone unfilled for months, a sense of global chic and retail smarts. Apple’s stores enjoy a reputation for sleek presentation and excellent customer service. Ahrendts, who will start the job mid-year, is expected to broaden that aesthetic into China, where Apple lags, and online, where the company’s approach to connecting with customers and making sales is lackluster.

Doug McMillon —​ CEO, Wal-Mart Stores Inc.

McMillon has a fabled history with the world’s largest retailer not seen much anymore these days: He got his first job at a Walmart warehouse as a teenager, and climbed the ladder within the company until he was named chief of international business in 2009. Observers say the Arkansas native, 47, is full of Southern charm, company ambition, and corporate smarts. He also has plenty of challenges ahead of him as the stalwart retailer faces changing demographics and attitudes, along with swiftly changing retail dynamics.

Laurent Potdevin —​ CEO, Lululemon Athletica

Potdevin is succeeding a CEO, Christine Day, who is widely credited with helping boost Lululemon’s sales and revenue and fostering its successful expansion across the country and worldwide. But he also arrives after a rash of quality issues, declining sales, and an ugly public relations debacle created by the brand’s founder. Potdevin hails from TOMS, where he helped build a successful brand perceived as socially conscious and friendly, and observers expect much from him as Lululemon strikes back out into what is now a more competitive yoga-clothing retailing environment. As it tries to gain back its footing, Potdevin’s past experience at a high-end snowboard company with a cult following, along with his own enthusiasm for yoga, may also serve him well​. Maybe under Potdevin, Lululemon can win back women customers and win over men, as well. At this point at Lululemon, who knows.

Tony Spring —​ CEO, Bloomingdale’s

Spring has the unenviable position of trying to fill the shoes of a much-lauded executive, Michael Gould, who inspired employees, is credited with giving the company strength, and is leaving among plaudits. Still, Spring, 48, was one of those inspired employees, having worked for Gould for 18 years, and his ascension is a natural one for Bloomingdale’s. Spring is clear that he wants to shine the retailer’s luster — building on Bloomingdale’s as a shopping destination, with unique attributes and even signature products, both in-store and online. Spring talks about maintaining the retailer’s sense of specialness and exclusivity, a neat trick for a company that also wants to expand. But “growth isn’t a strategy, it’s a result,” Spring has said. 

Jerry Stritzke —​ CEO, REI

Stritzke​, 53, has the youthful swagger of someone who wrangled cattle in Oklahoma as a kid, and the retail experience of someone who was, for five years, the president and chief operating officer of publicly traded luxury brand Coach. REI, a coop-based outdoor clothing and gear retailer based in Kent, Wash., has had only seven CEOs since its founding in 1938. The retailer has 132 stores in 33 states and 5 million members, and it’s feeling the pressure of Amazon (of course), other outdoor retailers like Cabela’s, and ambitious department stores like Nordstrom.  Stritzke​ told the Seattle Times that he’s pleased to see that 20% of REI’s sales come from e-commerce, and the company has plenty of cash on hand to invest in technology. But Stritzke​, an outdoor enthusiast himself, has spoken energetically about REI’s “authenticity,” so he will likely work to build up the REI brand and expand it beyond its West Coast comfort zone.

Myron E. (Mike) Ullman III —​ CEO (again), JCPenney

Mike Ullman’s LinkedIn profile still lists him as “US and international retail CEO (retired).”  But Ullman is not, in fact, retired anymore; he’s been brought back to his old job at JCPenney. The company, in an April 2013 move seen as desperate, sought Ullman’s return to clean up a mess made during the tenure of CEO Ron Johnson, who replaced him in 2012. Ullman himself left the company amid blame for falling revenues and stock prices — but the drastic changes made by Johnson, though famous for helping usher in the era of the much-lauded Apple Store, were seen as imprudent, too far flung from JCPenney’s fundamental culture, and just basically yielding disastrous results. Ullman, 66, has already had to field several challenges, including a stock plummet of more than 60% last year, a rough holiday shopping season, and the announcement Jan. 15 that it would cut 2,000 jobs and close 33 stores by early May to save $65 million. He has a small window of time and space to convince JCPenney customers and investors that he can bring the retailer back to the future — and a bright one at that.