Skip the Dishes, the online food delivery network, has been an asset to young people in Winnipeg since it started, feeding the less gifted cooks and busy corporate climbers among them – and, inevitably, the hungover ones.
“When we first built Skip the Dishes, we originally thought it would be for just corporate users working late nights,” says president and co-founder, Josh Simair.
“All of sudden, there’s the huge hangover crowd. So in Winnipeg, Stella’s Saturday and Sunday morning, you’ll see dozens of food couriers going in and out, servicing Winnipeg’s hangover crowd.”
That aside, new highly skilled graduates may soon gain a whole new appreciation for Skip the Dishes as part of its tirelessly growing young workforce.
The province is funding Skip the Dishes just over $400,000 to add to its staff and create a thriving national headquarters in Winnipeg.
Staff expansion is on pace with the tech company’s aggressive growth. “We’re taking a couple people a week basically,” says Simair.
“We went from three people last year, to 44 people now (across all the provinces). And we’re going to grow to about 100 in the next 12 to 18 months in Winnipeg alone.”
When it comes to the jobs that’ll need filling, they are diverse, spanning operations, dispatching, marketing and graphics, IT operations and development, human resources, administration and accounting.

Training and tax credit support are being facilitated by the province, as it recognizes that most new grads won’t walk into Skip’s doors prepared to work with its specialized technology.
“When people graduate from a Winnipeg educational institution or a Winnipeg university, you have a lot of skill that you need to do well in a career, but having a tech company, it’s very specific,” explains Simair.
“So it’s really getting people to understand the mindsets of a tech company. There’s new iterations coming out all the time… it keeps changing.
“We try to build everything that’s very intuitive and self-explanatory, but there is a bit of a gap for people to be trained on.”
The reason Skip the Dishes is so successful, and is the largest online food delivery network in Western Canada, is because of its technological sophistication.
“It’s nothing really that new for what we’re doing, it’s just that we’re the most efficient, cheapest and modern way to do it. We’re the only people using technology to automate the whole process,” says Simair.
“It’s a whole bunch of mathematics behind the scenes that goes on to make sure that the food courier picks up your pad thai very hot and then it comes to you hot too.
“There are trillions of factors every single night that we have to account for… and that’s all the work that we do.”
Its technology is about to become even more advanced with the development of an app which will allow customers to order from one of the many restaurants Skip the Dishes offers delivery for, and then watch the food courier in real-time and track its progress.
“We have the alpha testing of that food courier tracking and we’re addicted,” says Simair, who expects the app to roll out in September.
Because of its widespread automation which lowers the cost of offering the delivery service, Skip is constantly signing up new territories to add to its empire, and in established markets like Winnipeg, new restaurants approach Skip weekly.
The rapid growth makes it an exciting and unusually fast-paced place to work.
“It’s not realistic for a company to grow 20 per cent month-by-month, and we’ve been doing that repeatedly,” says Simair. “So people that join Skip the Dishes, join it for the experience.
“They get five years of experience in one year of work. And they get to try sales, try marketing, try support, try an IT implementation. All of these different pieces that maybe you do once a year in a different company, but we do it every month.”
One of the most exciting things about the company is that it provides an opportunity to keep some of the top-performing, tech-savvy graduates right here in Winnipeg. “We hire a lot of U of M, U of W and Red River students and new graduates. So we’re a very young team.
“The A++ students from Asper normally would go to New York or London or Vancouver, and now we’re able to offer them a job that’s very challenging,” says Simair.
“So it’s an opportunity for these students to actually have a high-performance, meaningful job right here in Winnipeg.”
Touring Skip’s headquarters at the Manitoba Technology Accelerator building, one can quickly pick up on Skip’s youthful, tech-heavy atmosphere.
Skip is absorbing the most real estate on the fifth floor on McDermot Avenue, with fixed-gear bikes lining the outskirts of its designated area and a ping pong table doubles as a workspace for people on laptops in the centre of the room.

Each workstation has up to four monitors, and the median age appears to be about 26. “We just say deep twenties. It makes us sound older to investors,” jokes Simair.
The company uses recycled computers, monitors, and office chairs, and it pinches every last penny by drinking bad coffee in its low-rent location in the Exchange District. “It’s very low cost of business here,” says Simair. “Cheap rent gives you a licence to be creative
“Being a new Winnipegger, I understand. I like a deal too,” laughs Simair.