From Tech Blogger to CEO

Today’s Small Business section of the Financial Post has a great article on Benjamin Yoskovitz of In a article titled A Standout among Movers and Shakers, Rick Spence asks the former tech blogger turned CEO what he’s learned over the last year since taking the helm. Yoskovitz sums it up with three challenges – money, the market, and hiring.


Standout Jobs needed capital to survive more than a year of zero revenue as the team researched its market and tweaked the product. Yoskovitz had written about raising venture capital but had never gone to anyone on bended knee. He estimates he’s made 30 presentations in Montreal, Toronto and New York City – some successful. “I had heard that 60% of a tech CEO’s job is raising capital, but I don’t think I believed it,” Yoskovitz says.

When you’re asking for money, he says, “You don’t feel like you’re in a position of power or equality … it doesn’t allow for the most confident of answers. You feel like you’re being lectured to rather than running the meeting.”

He learned that the secret of controlling the conversation is preparation: The more embarrassing questions you anticipate, the stronger you feel in the middle of a pitch.

The Market:

When the partners dreamed up the idea, they were aiming at firms like themselves: small startups with big dreams and no money, competing for a scarce number of programmers who can be motivated by distant fences. They soon realized that market was too small, and revised their plan to serve bigger niches: businesses less than 500 employees and medium-sized businesses with 500 to 1,000 employees.

Where many firms skip market research in their dash for dollars, Standout Jobs carefully reviewed the competition, demonstrated the product to potential customers, and researched the budgets of corporate human resource departments.


Standout Jobs faced the classic startup conundrum: It needed world-class technical and sales people, but was unable to offer big salaries or even a proven product. It came up with a viral Web video that let people know Standout Jobs was up to something great — without spoiling the element of surprise. That attracted the right kind of people, Yoskovitz says — the one software developer in 100 who loves the idea of working on something special and taking a risk.