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Canada’s Jay Rosenzweig on Hiring and the Silicon Valley Myth

Relationships are everything. And people form relationships. So hire the right people first.

That’s the thinking behind Rosenzweig & Company, a think-tank, well known for executive hiring and its advocacy for the advancement of women in business.

Grit Daily caught up with eponymous CEO Jay Rosenzweig to take a deeper dive into all things tech, recruiting, and myths of Silicon Valley.

  1. Jay, in addition to providing executive recruiting services to large corporate clients,you’ve carved out a reputation for successfully identifying, mentoring and scaling businesses that transform the way we work, live and play. Particularly those in the technology and entertainment space. What prompted you to branch out in that direction?    

Jay Rosenzweig: As someone who started a firm from scratch, I think I have a natural affinity

Rosenzweig and wife with Canadian Prime Minster Justin Trudeau.

with, and respect for, entrepreneurs. I understand the challenge of not only putting together an initial team, but also the need to bring on people at the right time to achieve a sustainable business model. As for technology, I am absolutely fascinated by the frontier technologies that are emerging in our world, and feel privileged to be at the centre of a lot of it. The stakes have never been higher in terms of the effects of innovation on the future of our world.  And I care deeply about the welfare of our world. Whether it be my board work on my mentor Irwin Cotler’s Raoul Wallenberg Centre For Human Rights, or my work in the technology space, I want to leave the world in good hands for our children, grandchildren, great grandchildren and beyond.

The workforce will be drastically different before we know it, and I fear not enough people are paying attention to this potential looming crisis. I believe education is on the verge of a big transformation. New ways of solving healthcare problems are emerging. I am fascinated by the future of transportation.

Consumer behaviour is changing. And so on.  I find myself in the thick of it with brilliant founders in all of these areas. I have never felt so exhilarated. Playing a role in helping to develop new business models and paradigms and behaviours that influence consumers in positive ways is very exciting to me.  The power of the influencer in this day and age is staggering, and I have been working on ways to exploit that for the good of society. I am also a music lover. That’s how Derrick Fung originally caught my eye – I thought his start-up, Tunezy, was amazing, and it launched him into Forbes 30 under 30 award status.  And of course more recently he has launched Drop, a brilliant rewards concept aimed squarely at Millennials. I am fortunate to have been on Derrick’s advisory board since day one.

  1. You not only work with companies like Drop, but you often serve in an advisory capacity and even invest in some of them. What is your thinking when you do that?

JR: In terms of advisory boards, founders approach me because they feel I can bring something to the table in terms of guiding them as they look to take their business to the next level. As with so many things, the more you do the more you know – in this case, the more time you spend with entrepreneurs and startups, the more common patterns begin to emerge. You get a better understanding of the different stages companies go through as they develop. Ideally, this puts you in a position to avoid pitfalls, and to help founders capitalize on opportunities they may not always see.  

Given the vast network I have developed over the past two decades, I am also able to help founders with fundraising and business development.  

  1. What are some examples of startup pitfalls?

JR: One common mistake made by startups is waiting too long to add impactful executive talent and thus missing out on the potential advantage of scaling up a new concept or product more quickly.

Another pitfall comes when start-ups predominantly hire people who are clones of themselves. I am a great believer that diversity – in every sense of that word – makes for better, more effective high-performance teams.  

  1. Derrick Fung decided to select Toronto, rather than a more obvious hub like Silicon Valley, as the headquarters for Drop. Is it difficult to get great tech talent to consider destinations other than California?

JR: First off, I would say it is a bit of a myth that all of the action is in Northern California. Austin, Texas, for example, is a huge center for the development of gaming apps. Places like Denver, Seattle and Los Angeles all have very vibrant tech start-up markets. Speaking specifically of Canada, Toronto has a lot to offer in terms of its technology ecosystem, its educated workforce, it’s good air links and quality of life. What is interesting with regard to companies like Drop is that they are able to attract highly skilled individuals out of places like California and New York.

Ian Logan, who was Director of Engineering at Airbnb in San Francisco, came back to his home base in Toronto to head up engineering for Drop. We recently recruited of an outstanding NYC based candidate to be Drop’s Chief Revenue Officer.  Drop has also proven that it can attract not only great candidates, but prominent investors out of Silicon Valley and New York, including Venture Capital firms such as NEA, Sierra Ventures and White Star. We have been able to attract some truly excellent investors and candidates to Canada over the past number of years. And, yes, the political climate is likely a factor.

  1. Do you tend to look at a different type of candidate when recruiting for an emerging growth venture and, if so, do they tend to come from similar type companies?  

JR: There are candidates out there that I would describe as serial entrepreneurs – they have a track record of success scaling up businesses for three to six years and then moving on to the next opportunity. They thrive in the start-up environment and have a high probability – not a guarantee, mind you – of replicating past performance. I would describe that type of candidate as a safer bet for the launch phase of a company.  But they might not be the right person as the company matures. In some instance, this will be because they simply get bored – they want a new challenge, a new hill to climb. Or sometimes they don’t have the skill-set to maintain a business over the long haul. The best entrepreneurs understand their own strengths and weaknesses and surround themselves with the best possible people, individuals who are a good cultural fit and can bolster the skill set of the leadership team.