Highline Beta Investor Profile: Jay Rosenzweig

Jay Rosenzweig Investor Profile Image

As we continue to feature our investors and mentors at Highline Beta — in their own words — we’re excited to introduce you to Jay Rosenzweig, a trained lawyer, executive search strategist and team builder, human rights champion, environmentalist, and successful tech investor. We talk with Jay about the importance of finding and following your passion. Jay was also profiled in Forbes recently; you can read Icons: Jay Rosenzweig, A Man Of Many Hats And Talents to learn more. 

I’m Canadian, born and raised in Montreal. I studied philosophy and law at McGill University, where I  met a really important mentor: Irwin Cotler, a well-known international human rights champion who went on to become Canada’s Attorney General and Minister of Justice. If you fast forward to today, I’m chair of the board of his Raoul Wallenberg Centre for Human Rights. I began my career in law by articling at the law firm Pinkofsky Lockyear, a law firm that represented a number of clients who were wrongfully convicted. DNA technology at the time was becoming more and more reliable, and in a number of cases, the firm was successful for that reason. This in part triggered my interest in technology. 

Driving business growth through talent

I eventually pivoted away from law, when I saw a business opportunity in the executive talent strategy space. I joined a small boutique firm which eventually got acquired by one of the world’s largest search firms. It was a great experience for me. Ultimately though, I decided to break away and start my own firm to bring more customized solutions to the table for my clients, have the opportunity to work with entrepreneurs, and work all around the world. We’re now working for some of the biggest corporations in the world, and helping private equity firms change out portfolio company leadership post-acquisition. I also work with entrepreneurs, helping them scale their companies through talent strategy and executive team building, fundraising, business development and overall strategic and operational advice.

I invested in Highline Beta because I am extremely people-driven. People are the number one priority of the business — everything else is secondary to me, especially in the early stages. My whole core is about driving businesses through talent. That includes betting on individuals who I believe in, because inevitably the business will evolve, it will pivot, and the founder will add new elements to it and develop the original idea. Founders as the first priority principle led to some really great opportunities  – for example, I joined the Drop Advisory Board super early mainly because I believe so much in Derrick Fung. Yes, the loyalty and rewards space could use innovation, but what’s most important to me is Derrick is a rock star who could figure it out.

Focusing on the intersection of profit and purpose

It’s gotten to the point now where I’m on the board, typically the advisory board, of dozens of emerging growth businesses. We’ve gained a lot of traction focusing on the intersection of profit and purpose, doing good and making an impact in our world. One of my best examples of this is our annual Rosenzweig Report on Women at the Top Levels of Corporate Canada. My intent with that report, published for 16 years now, is to provide corporate leaders and boards with information that would put their own practices and progress into statistical context and perhaps inspire them to do better. 

“I am deeply curious about people and I love being helpful. When I work with young up-and-coming founders, I tell them, while it may sound cliche, it’s really about finding your passion.”

– Jay Rosenzweig

I believe strategic giving needs to be reinvented. I am inspired by a fantastic project launched in the wake of COVID-19 called Pandemic of Love, an incredible grass-roots volunteer initiative by Shelly Tygielski. She had this spreadsheet — it was so simple, she just wanted to match those in need of help with people who could give, just this 1:1 matching — and she’s raised $50M in the process, helping so many people. We live in times when many businesses will need reinvention, and when I work with young up-and-coming founders, I tell them, while it may sound cliche, it’s really about finding your passion. I am on a number of purpose-driven boards. Black North is an example of a board I am on that is taking strides to change the system when it comes to upward mobility and economic empowerment in the Black Community. It is gratifying to be part of an organization that is making a difference. Hundreds of companies have signed a pledge to do better with respect to Black executives in their leadership ranks through the Black North Initiative. 

In my corporate executive search and team-building work, we look at filling all kinds of C-level functions, and of course the CEO function at a certain point in time, as well. We help founders build that succession plan where they sometimes hit the lifespan point in their business to take it from a $20M to $40M business, into the hundreds of millions territory. We often work with VC firms on filling these very fundamental roles; one that comes to mind is eSight, where we brought in a tremendous new leader, who not only had the experience of taking the business to the next level and the corporate development experience, he also cared about the company’s mission on a personal level.

Sky’s the limit

I am deeply curious about people and I love being helpful. I’m able to do the work that I do because of all the great experience and connections I’ve been so fortunate to develop over the years. I’ve seen enough companies succeed, had some good exits, and I think that Marcus, Ben, Lauren and the team at Highline Beta have developed a platform and a program which is super strong and stable. There’s so much more opportunity to engage with corporates and continue to scale this up. I really think the sky’s the limit — that’s how big this can be.

“I think that Highline Beta has developed a platform and a program which is super strong and stable. There’s so much more opportunity to engage with corporates and continue to scale this up. I really think the sky’s the limit — that’s how big this can be.”

– Jay Rosenzweig

Now that Highline Beta has so many test cases proven out, its next level of growth will be a lot easier to achieve, as long as they have the right people behind it to support, a great eye for talent and for opportunities, not to mention deal flow. I’m really excited for the future of Highline Beta. I’m a very, very happy investor, who is already reaping the rewards — we’re playing with house money right now, which is a wonderful place to be; we’re getting financial returns already; it’s really an investor’s dream.

About Jay Rosenzweig 

Jay Rosenzweig, the founding partner of Rosenzweig & Company, is an expert in designing, building and attracting world-class teams. Prior to joining the search industry, Jay earned three degrees at McGill University: Philosophy, Civil Law, and Common Law. Jay has been immersed in global human rights causes for well over two decades. He is Chair of the Board of Irwin Cotler’s Raoul Wallenberg Centre for Human Rights and has been internationally recognized for the Annual Rosenzweig Report on equality, which he has published for the past 15 years. Jay invests in and advises several leading-edge businesses, including: Hyperloop Transportation Technologies, the next quantum step in transportation; Winston House, a global community of young creators sharing a passion for people, music, art, sports, travel, brands, and activism; Drop, the leading millennial coalition loyalty program; and many others. Jay is an avid songwriter, having collaborated with well-known recording artists and written original music for each member of his family.

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