Women in Dealmaking: A Chat with Janet Bannister, Partner at Real Ventures

Women in Dealmaking: A Chat with Janet Bannister, Partner at Real Ventures

In this interview series, we profile trailblazing women working in M&A, private capital and finance who are driving deals. We highlight their experiences and achievements, and share their insights on what the industry can do to ensure that we see more women on deal teams and at the dealmaking table. In celebration of International Women’s Day (March 8), we sat down with venture capitalist Janet Bannister, Partner at Real Ventures, to discuss the importance of mentorship, gender parity, and diversity in the investment world.   

What one quality do you think is most critical to succeed in the investment world?

There are many skills required to be successful in the investment world, including the ability to quickly understand different industries; the ability to anticipate the likely impact of technology and other trends on those industries; and the ability to analyze a company from a financial and strategic standpoint.

But I think the most critical quality is the ability to build trusted relationships with people. Only if you have a solid foundation of mutual trust and respect, and only when you can communicate effectively and empathetically, can you begin to leverage your other skills that are required to be successful in the investment world.

In your experience, what’s the number one reason that VC investment deals go bad?

One of the biggest reasons that deals go sideways during an investment process is because one – or maybe both – of the two sides have not been fully transparent or are inconsistent during the process. For instance, a company may not reveal all of the “skeletons in the closet” up front and then when they come out during the due diligence process, they can reduce the perceived value of the company, but more importantly, can result in a loss of trust between the investor and the company. Similarly, some investors shift their positions after a term sheet has been signed and this also can result in a loss of trust between investors and the company.

What do you find most rewarding about the work you do?

My work is extremely rewarding. I have tremendous respect for the entrepreneurs and other company builders with whom I work every day: they are smart, passionate, driven people who work hard every day, taking the “road less traveled” because they have a vision and the ambition and determination to see that vision become reality. I am truly honored to have the opportunity to work with them and in some small way, help them achieve their full potential.

The industry is changing rapidly: what do you think the investment landscape will look like in 10 years?

Like all industries, the investment industry is changing rapidly. Artificial intelligence is poised to transform every industry, including the investment industry. In the future, more investing decisions will be based on quantitative inputs and algorithms rather than judgment and instinct. That being said, I believe that the human element of the industry will be just as relevant – perhaps more relevant – in the future: understanding people, establishing trust, building credibility, communicating effectively – these things will always be fundamental to an individual and a firm’s success.

Did you have a mentor or role model that encouraged you to enter the investment world?

I am very thankful to have met the three founding partners of Real Ventures five years ago. I had never considered a career in venture capital but they encouraged me to join Real, showing me that my experience as an operator, entrepreneur and strategist lay a solid foundation for excelling in the VC world. They also showed me that Real’s success is based on giving back to the community, working with the highest levels of integrity, and being relentlessly focused on doing what is right for our founders. These things, in addition to an alignment between my values and those of Real, made it an easy choice to join.

According to a leading financial services recruiter, when they post an entry-level investment banking or private capital job opening, typically only 8-10% of the applicant pool is female. What do you think scares women away, and what can be done to attract more women to the profession?

I do not think women are scared; they may not see themselves in the investment industry because men are seen to hold the vast majority of senior leadership roles in the industry. In order to create a more diverse workforce – which we know from extensive data will result in better financial results – we need to highlight the successful women in the industry, publicize the rewarding career opportunities available for everyone, and develop recruiting strategies that reach a broader talent base.

Does your firm have initiatives in place to encourage gender parity and diversity?

Gender parity and diversity are extremely important considerations. At Real Ventures, we think about it at three levels: 1) within the Real Ventures team; 2) amongst the founders in which we invest; and 3) within the teams of our portfolio companies. We have initiatives and programs in place at each of these three levels.

How is more female representation changing your industry?

Studies have shown that more diverse workforces have better productivity, are more creative, and lead to better financial results.

Over the last several years, there has been an increase in the female representation in the venture capital industry. Studies have also shown that when venture capital firms have more female representation at the partner level, they are more likely to invest in female entrepreneurs. Therefore, as our industry continues to increase in diversity, I am optimistic that we will also see more diversity amongst tech founders.

What positive changes have you seen since you started in your career?

There has never been a better time for women in venture capital investing and the tech industry. I believe that these industries offer tremendously challenging, exciting and rewarding careers and I strongly encourage women to explore career opportunities in these fields.

There are several initiatives that are continuing to drive positive change for females in technology and investing, including #MoveTheDial, Women in Capital Markets, and theBoardlist.

What advice would you give the next generation of women preparing for a career in M&A, private capital or finance?

Private and venture capital need smart and ambitious women. It is not an easy career path, but it is a fascinating, gratifying and exciting one. For women who want to enter the field, I would say, “Go for it!” Build relationships with people in the ecosystem, attend events, find mentors, and always be trying to learn more.


Janet Bannister

Janet Bannister is a Partner at Real Ventures, a leading source of capital for Canada’s game-changing entrepreneurs. Janet has led investments in over a dozen companies and works actively with founders to help them build large, industry-defining companies.

In addition to working with her large portfolio of rapidly growing tech companies, Janet is very active in the Canadian tech ecosystem; she is on the Board of Communitech in Waterloo and Vector Institute in Toronto and is an active advisor at MoveTheDial, DMZ and Creative Destruction Lab.

In 2004, Janet launched Kijiji.ca and grew it to become one of the most visited websites in Canada. Subsequently, she led the Kijiji Global business, launching the site in new countries and accelerating growth in North America, Europe, and Asia.

Janet also spent four years at eBay in Silicon Valley where she helped transform eBay from a collectibles to a mainstream marketplace. Janet started her career as a Brand Manager at Procter & Gamble and then joined McKinsey & Co. where she was an Engagement Manager.