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Only one special piece of equipment is issued to each Pineapple Express cannabis delivery driver: a plastic blue tub.

The cooler-sized vessel, meant to store cannabis due for delivery in the back seat or trunk of a driver’s personal vehicle, is the kind available for less than $20 at any hardware store. If it weren’t for the company shirts and ID badges the drivers wear while on duty, they would be next to impossible to distinguish from anyone else driving around town.

Just before taking Cannabis Professional along for two deliveries in the Winnipeg area, regional manager Curtis Ling explains that the low profile is intentional.

“We pride ourselves on discreetness, not every customer is going to want a pineapple siren going off in front of their house when their weed is being delivered,” he said. “People might think there is a stigma or that neighbours will judge.”

Drivers get an allowance for their mileage, and details such as their exact speed and location are tracked in real time while they’re on duty. There are a dozen drivers based in Winnipeg – with at least three on the road at all times during business hours – and Mr. Ling also recently established teams in Regina and Saskatoon.

Pineapple Express also delivers to medicinal patients in the Greater Toronto Area, but it has currently reached the limit of expansion around cannabis because of provincial laws. Manitoba and Saskatchewan are the only two jurisdictions in the country that currently allow private companies to deliver legal recreational cannabis.

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Curtis Ling, regional manager of Pineapple Express, delivers packages of cannabis to clients in Winnipeg.JOHN WOODS/GLOBE AND MAIL

Typically, each shift starts around midday with a trip to one of Winnipeg’s five legal cannabis stores for products due for delivery. Pineapple Express never stores cannabis overnight, usually taking it directly from stores to customers, which Mr. Ling says reduces the total volume of cannabis a driver must carry at any given time.

Three drivers each working a full day might make about 100 deliveries between them, Mr. Ling said. On its first two days of operations in October of 2018, he said, Pineapple Express Winnipeg was handling upward of 1,500 deliveries a day.

Much like the food delivery business, the weather can often dictate demand.

“We never really know how a day is going to go,” Mr. Ling said, “we had a massive rainstorm here last week and deliveries went through the roof, it was all rush rush rush.”

Drivers can pick up as many as 30 customer orders at a time on an especially busy day, he said. That means if each order contained the maximum personal limit of 30 grams, a delivery vehicle could hold close to a kilogram of dried cannabis inside that plastic bin.

It takes a certain type of person to do the job well, Mr. Ling explained, with some either taking the role too seriously or not seriously enough.

“In the past I actually had to get rid of a guy because he felt like he was in more of a security guard role,” Mr. Ling said, “we got a couple of complaints and talked to him and he wasn’t able to change, which is unfortunate.”

Another driver was fired for leaving the door to his vehicle unlocked while bringing a delivery to a customer’s door. “He was back in a minute but we still can’t have that,” Mr. Ling said.

Transparency is a key value that Mr. Ling hopes will give Pineapple Express an edge in a business that competes head-to-head with illicit delivery companies. A quick online search reveals no shortage of companies offering to deliver illicit weed to Winnipegers’ doorsteps.

Mr. Ling says his drivers are faster and more accountable than their illicit rivals. “We’ve never really had a problem with an order, but if we did the customer would hear from us and get a quick and full explanation, we also pride ourselves on being punctual, it is part of our job,” he said. “Before, you could have been waiting around all day for your ‘guy’ to show up and what consequences would there be if he didn’t?”

Having worked at UPS for 17 years before going into the cannabis delivery business, one similarity Mr. Ling was surprised to discover was the overall diversity of his customer base did not change.

“You would think it would be the typical stoner type of customer,” he said, “but it is actually anybody and everybody, different ages, classes, and cultures.”

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