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Andrea Stairs, managing director, eBay Canada.

Rachel Idzerda/The Globe and Mail

Andrea Stairs recalls her darkest days as head of eBay Canada in early 2009, after the company's U.S. parent dramatically scaled back its operations and left her with just five staff members – a painful 80-per-cent cut.

She briefly considered quitting.

But using her pragmatic approach to troubleshooting, she sought advice from confidants – her "personal board of directors" – and contemplated what she could learn from the difficult eBay reorganization, ultimately deciding to stay at the e-commerce company.

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The experience is reflective of the ups and downs she has encountered in her business career, which peaked about 16 months ago when she was promoted to managing director from sharing the country-manager role with a colleague at eBay Canada.

"I think there have definitely been some U-turns and some shifts and certainly some surprises," Ms. Stairs, 41, says about her career during an almost 3-1/2 hour lunch at Le Sélect Bistro, which is a convenient two-minute walk from her downtown Toronto loft-style offices.

"The eBay reorg was a surprise. … No one looks back and says, 'Ach, I learned so much when things were easy.' That doesn't happen. You look back and think, 'That was a really tough period but I learned so much.' "

Learning from setbacks and plotting practical solutions are key approaches that have helped define Ms. Stairs both in her business and personal life.

At eBay.ca, she will need to tap into those attributes more than ever as the company gears up to take on the fast-growing U.S.-owned titan Amazon.ca in an increasingly tight retail landscape. She also needs to step up her focus on transforming eBay.ca's image from its roots as an auction site for used goods to its emphasis on selling new products.

Canadians spend more than $1-billion annually on eBay and 80 per cent of the items they purchase are new rather than second-hand. It's a critical time for parent eBay Inc. of San Jose, Calif., as it enters a new era after having recently spun off its high-performing PayPal division, leaving it to concentrate on the slower-growing retail marketplace. The company has recently hired seasoned retail executives to steer it toward offering merchandise that its research indicates its shoppers will covet, rather than just operating as a tech firm peddling sellers' own product choices.

Daniel Debow, a serial tech entrepreneur (co-founder of Rypple and Workbrain) and former classmate of Ms. Stairs at the University of Toronto's joint law and MBA program, says eBay now has to come up with new innovations as quickly as its rivals do.

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The company grew enormously in Canada and has to keep doing that, says Mr. Debow, who influenced Ms. Stairs in her decision to join eBay a decade ago. "Andrea is super levelheaded and very analytical – she cuts to the chase."

In her personal life, she also shows a healthy dose of pragmatism. She chose the French bistro for our lunch because it's familiar and close to her offices. She always orders the same thing, and does again this day: a grilled four-ounce centre-cut of Alberta beef filet with arugula, chick peas and tomatoes. She sticks to routines for basic tasks and leaves to-do lists around the house for herself, her husband and nanny. "You save your thinking for questions that require more bandwith."

She's an eternal optimist who covets efficiency. When she and her husband, Nini Krishnappa, a Bank of Montreal communications executive, head to an event, she likes to leave the least amount of time necessary to drive there, assuming they'll get green lights. He, on the other hand, prefers to give themselves twice as much time to arrive, anticipating slow traffic. As Mr. Krishnappa puts it: "It makes for some intense bargaining … maybe it's somewhere in between. That's where we usually end up. ... I don't think either of us could have had a successful marriage with someone who is a pushover."

"It drives my husband nuts because I'm always thinking that everything is going to go perfectly," Ms. Stairs says with a laugh. "Generally speaking, most things go right, in my experience."

Some things have gone awry. When she was 9 and living in Montreal, her parents separated. Her mother, Harriet Stairs, at the time a human resources executive with Bank of Montreal (no ties to Mr. Krishnappa's position) and one of the few senior businesswomen in the country, moved with Andrea, her younger brother Colin and their nanny Mimi ("she was very much a second mom to me") to Toronto as the bank relocated its headquarters. Her father, an engineer who ran a company, stayed in Montreal and remarried.

Andrea quickly embraced her life in Toronto as a student, attending the private Branksome Hall all-girls school. She says her single working mom was her role model. Her mother, who progressively got promoted within the bank's top ranks, would often come home from work and "debrief" Andrea about her day, giving her daughter a glimpse of the working world. Andrea didn't think twice that her mother missed her field-hockey games.

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Harriet Stairs, in her mid-60s, says her daughter has always been ambitious and quick to pick up on concepts. "I used to call her my mini-mogul," the now-retired Ms. Stairs says warmly.

Andrea picked up tips from her mother, such as establishing a personal board of directors of trusted friends and colleagues to use as a sounding board for critical career issues. Her mother "has been a hero of mine my whole career – my whole life," Andrea asserts.

Her close ties to her mother helped her realize early on that she wanted to go into business. But her mother urged her to study something different in her undergraduate years at McGill University, reasoning that she would inevitably go to graduate school for a specialty. She took undergrad medieval medical history after being inspired by the professor who taught it. "It makes for somewhat crazy cocktail conversation," she says with a laugh, sipping her second glass of Perrier water on this steamy summer day, the humidity seeping into the restaurant from the open patio doors.

At U of T's joint law and MBA program, Ms. Stairs was part of a tight-knit group of students, some of whom, such as Mr. Debow, now a senior vice-president at Salesforce.com, remain trusted advisers. "I loved the MBA school," she says. "It confirmed what my 12-year-old self had been saying – a career in business was definitely where I was heading."

She specialized in corporate finance and went on to work summers at BMO and Toronto-Dominion Bank, toiling long hours – once 120 hours in six days – on big mergers and acquisitions. "It's brutal," she says. "It solidified for me that I didn't want to work that hard." She declined an offer to remain with TD's M&A group and moved to Ernst & Young in M&A for mid-sized telecommunications companies. Again, the hours were gruelling.

"I remember working so hard and coming home and getting into bed with my Lean Cuisine fettuccini, opening it up and, like, 'This is the best part of my day.' That was an 'aha' moment that I might be in the wrong career." But she was able to analyze what she did like: strategy and problem-solving for big companies dealing directly with consumers. "I'm a girl who likes to read Vogue cover to cover."

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She got her next job at Gap Canada after hearing from a friend's brother, an HR manager at the retailer, that he was looking for someone to work on strategy. "He hired me for a job that, on paper, I was completely unqualified for."

She says her two years at struggling Gap were disappointing as she got bogged down by what seemed to her to be "arbitrary" decision-making. She left to do independent consulting – with a nagging feeling she was too young to do that for the rest of her life.

Within a year, Mr. Debow helped connect her to eBay.ca, even though she had no tech background and no interest in joining the company. EBay.ca was looking for a strategist to help improve its operations and Mr. Debow urged her to take the job.

Her first position at eBay.ca was developing strategy and turning around its car sales. She slashed the fees for selling used cars on eBay.ca to $5 from $40, which drew more customers and helped revive that business. (Today, eBay.ca sells used cars on its Kijiji site and charges no fee; Ms. Stairs doesn't oversee Kijiji.) She went on to head eBay.ca's Quebec division and then marketing before becoming co-country-manager in 2009.

Today Ms. Stairs's wider task at eBay Canada is to persuade shoppers to think of it as a retail destination for new or used hard-to-get merchandise, in a wide array of price ranges, even as the market gets more crowded. It is taking a more active role in mining its data to pinpoint inventory its sellers should stock. At the same time, eBay faces a growing number of rivals. She says the strategy is working, although the company doesn't break out its results here. "It's a really healthy business in Canada," she says.

Still, to underline her challenge, in the fall of 2013 eBay.ca was overtaken by Amazon.ca in web visits among Canadian desktop users, according to researcher comScore. She counters that eBay has doubled down on its mobile business and about 50 per cent of its traffic is mobile, which is growing quickly.

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On this day, she is a walking billboard for eBay.ca, sporting two chunky strands of a multicoloured Swarovski crystal necklace by designer Rebekah Price (available on the site for $99 each) to complement her off-white dress. (She usually wears jeans at the office.) Her swanky Cartier Tank watch is an eBay.ca purchase for $1,000, about $5,000 less than what it would have been in a store, she says.

At home, Ms. Stairs says she feels no guilt about leaving her two young children with their live-in nanny, Melinda, as she heads for work, just as her own mother did. The younger Ms. Stairs is usually home from work at about 6 p.m. and spends 30 minutes playing with the children and reading them stories before putting them to bed at 6:30, when she and Nini have dinner before they both settle in for more work. She tries to manage her business travel (such as monthly trips to head office in California) so that it doesn't overlap with Nini 's out-of-town travel.

"For us, having Melinda is essential to managing the home life," she says. "I think it's important that our kids see the reality – I think it's important that they see the kinds of trade-offs we're making. "My kids are 4 and 2. They inevitably say in the morning: 'Don't go to work.' I say, 'No, I have to go to work. That's my job,' and I think that's good for kids to see. They'll have to eventually go to work themselves."

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Andrea Stairs, managing director, eBay Canada

Age: 41

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Place of birth: Montreal

Education: Branksome Hall; McGill University (BA); University of Toronto's Faculty of Law and Rotman School of Management joint law and MBA program (LLB and MBA)

Family: Married seven years to Nini Krishnappa (Catholic ceremony followed by Hindu blessing); two kids, William (Willie), 4-1/2, and Caroline, 2

Favourite vacation spot: Métis-sur-Mer, an anglophone enclave on Quebec's Gaspé Peninsula, where her family has spent summer vacations for generations

Favourite activities: She loves watching football ("Go Bills!") and playing tennis

Guilty pleasures: "Vogue magazine, a nice glass of white wine, award shows and red-carpet specials

On being a woman in a male-dominated sector: Is aware of potential roadblocks, so she runs the Women's Initiative Network at eBay to build career opportunities. As the head of a "remote" subsidiary, she fights for resources from head office, "a much bigger issue than being a woman."

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