shift manager

store manager

seasonal associate

gérant de commerce de détail

sales associate

Bootlegger

Prospective candidates may want to carefully consider work–life balance expectations, as availability outside scheduled hours, including days off, appears to be common.
Training and onboarding are not always consistent, with prior experience often expected to fill gaps. This can make it challenging for employees to feel fully supported, especially when raising questions or concerns.
Employees may face pressure to meet performance and sales goals despite ongoing staffing shortages, safety concerns, high-theft environments, and limited operational resources.
Communication from leadership can feel limited, with guidance frequently deferred to written policies rather than direct clarification or hands-on support.
Staffing levels are sometimes insufficient, which can result in employees working alone in situations that may feel unsafe.
Sales targets and bonus structures may be difficult to achieve due to factors such as outdated inventory, inconsistent pricing, limited size inclusivity, and frequent markdowns. Based on employee experience, the structure can give the impression that bonuses are intentionally difficult to attain, potentially functioning as a cost-containment measure rather than a realistic performance incentive. Reductions in employee perks during high-demand periods have also impacted morale.
The company has experienced financial instability in recent years, which appears to affect store-level operations. Leadership turnover and the departure of long-term managers suggest that some systemic challenges remain unresolved.
Overall, this role may require significant effort with limited support, modest compensation, and evolving expectations. Candidates are strongly encouraged to ask detailed questions during interviews and assess whether the environment aligns with their personal priorities and comfort level.
Applicants should also be aware that Bootlegger locations in Manitoba now operate under the Warehouse One brand, and similar operational conditions may apply.

What is the best part of working at the company?
Getting to try on jeans in the dressing room when days are slow, and also the customers were always pretty friendly. Also the discounts on the clothes was amazing 👏 🤩 

What is the most stressful part about working at the company?
Feeling like you always need to make the managers happy or you feel you could be replaced... and my coworkers being catty and i would say there was a certain clique there and if you didn't fit the bill, they didn't like you... I found that very stressful. Also running the till in a timely manner.

What is the work environment and culture like at the company?
The work environment is nice at first... they make you feel like your now part of something bigger then yourself, and the culture was well knowledgeable on all things jeans.. and they expect you to learn it all. 

What is a typical day like for you at the company?
I'd go into the store, change into work clothes, clock in at the till. Wait for customers, or fold clothes while you wait... sometimes you will do price changes on the clothes... but mainly it's a lot of standing around and walking around fixing clothes. And when a customer comes I'd go and say hello my name is ______, then ask them if they need any help today or if their just browsing... If they need help, you help them to the best of your abilities and if you can't, you see if a co worker can. 
Also cleaning out the change rooms after each person has been in there... and at the end of the shift I'd do about half an hour to an hour cleaning the store, sweeping, mopping, vaacuming... and then I can clock out and go home.

Back in 2013, I only stayed with the company as a sales associate for two and a half months. The job itself was pretty good actually. I was quiet and a little shy but I was learning on the job with zero experience in retail; the manager knew these details about me yet still hired me. I folded clothes, assisted customers, let them know about promotions, used the cash register, etc. I made a few mistakes here and there, such as not folding something properly or accidentally putting a shirt in the wrong spot in the store. Overall, I'd rate myself as a sales associate a 7/10; never late and was polite to customers and did my job to the best of my ability. Worst part was the cattiness, shallow, high-school-like environment I was working in with my coworkers and manager. I graduated high school that June and I thought I escaped all the drama...nope. They talked behind my back(and in front of me about me) and whenever I rarely did something wrong, they were pretty aggressive about it. The break hours were also wrong...I had a 15min for lunch for an 8 hr shift, but on our busiest days and when I'd work longer hours(10-12 hrs) I would still only get the 15 min. I have avoided that place like the plague since I quit...overall rating 3/10. I'm being honest, this is the worst job I have ever had.

I am so happy I got to experience working at bootlegger. I had invaluable training in retail as well as the opportunity to meet some amazing people. However the company is struggling to provide their customers with new and trendy product which in turn makes it difficult as an employee to sell. How can I justify to my customer that spending $50 on an ugly floral shirt I wouldn't even buy nor wear is worth it? I can't. Especially when it's the same ugly floral shirt they bought last year in a different colour. The company makes it extremely hard for the sales associates to sell product they don't stand behind or feel good about. In addition to it being very hard to push the customers into buying outdated product you also go into work and everyone's clique-y. They take 'bootlegger' group photos in which only a select few are invited to participate in, as well as gather and gossip about each other. The people I made friends with were like me. We were outcasts it felt like. The misfits. I would not work in bootlegger again even though I did gain a lot of great experience and some amazing friends.

Some days were fun, but it was pretty micro-managed. Quite a bit of back stabbing within the employees. Getting tired of quite a few things at Bootlegger. Management (Manager, Assistant managers, and shift managers) were quite often hypocritical. There were good and bad days.There has been quite a few days where it was so bad that I wanted to up and quit. I definitely learned a lot, for example, great customer service, folding clothes fast and neatly, and I have gotten pretty fast at ringing through people at the till. The hardest part of the job would be dealing with unsatisfied customers who don't like the policies or getting along with some coworkers. I have learned to just take a couple deep breathes and just do as you're told. The most enjoyable parts of the job were seeing friends, having good laughs when everyone was in good moods, stock, talking to some customers, especially the bootlegger regulars.

I really enjoyed this job, I had worked there for a decent amount of time so I became quite established. This led me to make connections with many of the regular customers, I knew a lot about the product so I could be informative to customers and newer employees. My manager gradually ended up giving me more responsibility with store closing and training and receiving shipments, etc. The hours were very flexible and with my seniority my manager was incredible accommodating if I needed to change my schedule, I was also very frequently asked to cover for other employees and often accepted, although I did have complete opportunity to say no. There was some turnover with the seasonal employees (which I started out as) but most of us stuck around and we became friends. We had team incentives and the managers often pulled them out of their own pockets. Holidays were hard work but we functioned exceptionally well as a team. I felt respected and valued as an employee which I value a lot, no matter where I work.

Having been with the company for a number of years and gone through the opening and closing of a store or two, we found out just how valuable we were as store staff: Easily replaceable, poorly paid and expected to sell product that was not popular/in style.

The store's culture is what made everything livable (since the wages were barely over minimum). We had an amazing team in most of our stores and people enjoyed working with each other.

Head office employed a number of people that were very out of touch with current styles and trends on more then half of the merch we sold, so we would be constantly selling the same product year after year in different colors, which doesn't work well int he fashion/clothing industry.
The company has gone through three President/CEO's in the last three years.

I had worked at bootlegger for a little bit over six months and I chose to resign because the manager at the store I was at did not understand completely that I was still a high school student. They booked me for shifts right after school and I would still make it on time, however it was cutting it close as my school finished at 3:35 and I started at 4:00. When I had asked for strictly weekend shifts my manager had made a comment about how the shift changing was too much. I realized that this environment was not the best situation for me. They also expect you to only wear bootlegger clothing brands. I'm a very petit person and most of their clothing would not fit me properly. Most of the staff were friendly and kind to me and I really enjoyed being around them. I had originally given my two weeks but agreed to stay until my manager could find a replacement as we had worked out the schedule.

A typical day at Bootlegger consists of providing excellent customer service and building a memorable rapport with our clients. Creating new looks and working with visual components to portray the latest trends and showcase product lines. The management is still in the process of putting together a great team but I have no doubts it will all work out. The co-workers were diverse and fun to be around, they really contributed to the atmosphere of the store as a whole; friendly faces and colourful personalities. Overall the role in which i filled challenged me daily and gave me the drive to succeed and learn new things. I would have to say that the best part of my job was building a relationship with customers and having the satisfaction of knowing I made an impression and assisted in meeting their needs as a fellow consumer.

 I worked at Bootlegger for a total of six months and personally would not recommend it to others. Pressure to sell was extreme and you had to practically badger customers. Not only this management would talk down on other colleagues to myself. Even after consistently talking a person down they would not fire them... management for the most part was extremely unprofessional and as a sales associate of only three months at the time I was helping with the training of a new manager. This job was extremely toxic for little pay and little recognition 

Top Job Titles	Average salary
Shift manager 7 salaries reported	$15.67 per hour
Store manager 3 salaries reported	$43,833 per year
Seasonal associate 5 salaries reported	$16.48 per hour
Gérant de commerce de détail 5 salaries reported	$19.40 per hour
Sales associate 4 salaries reported	$15.20 per hour

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