The Big Read

‘Things get harder as you build’: After two huge fundraising rounds, Clearco wrestles with high expectations

One day late last summer, Clearco called its sales staff to a Zoom meeting to discuss its goals for the fourth quarter. It had been a wild year already: the company had hired hundreds of employees, launched in new markets and pursued a growing suite of products. Over the past few months, it had raised more than US$550 million in two separate fundraisings, including one led by global investment giant SoftBank. Riding a wave of pandemic-fuelled demand for e-commerce, the Toronto-based fintech had secured a valuation of nearly US$2 billion, making it one of Canada’s most prized startups.

But Clearco hadn’t called its salespeople in for a victory lap. Instead, the company’s vice president of revenue, Stephen Defina, delivered some unsettling news: the company was paying sales staff more than they were bringing in, and things would have to change. According to three former employees who were there, Defina went on to break down the numbers showing the loss Clearco was taking on its salesforce, many of whom had only just joined the company. As they logged off the meeting, some staffers began to worry they were going to be fired.

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