Techs and the City – Deborah Jackson


Much has been said and written about the lack of women in the tech sector, be it as investors (or associates), founders or in management positions at major companies. Is the problem the old boys network – or that success in technology is seen as a young man’s game?  In this series, we speak with some of the top industry women in New York as they discuss the challenges they face, the perceptions that need to be changed and the work that’s being done – or not – to help to promote women in tech. 



Deborah Jackson, founder and CEO of Plum Alley, an e-commerce and crowdfunding site for women’s innovation, and a Founder of Women Innovate Mobile Accelerator, an accelerator that invests in women-founded mobile tech companies gives her insights on what it’s like being one of the fairer techs.

What was/is the biggest challenge facing you as an female entrepreneur?

There aren’t enough of us and there should be more. We could all benefit by connecting and advancing each other the same way men do, and it would be a lot more fun.

What can be done to further promote female entrepreneurship in New York?

The city should declare a day to celebrate and recognize women entrepreneurs. Perhaps a women’s entrepreneur day, where people are encouraged to buy from female founded companies in the way that people buy from small businesses on ‘Small Business Saturday.’

What is being done that you like presently?

The topics of women entrepreneurship and women leadership are being discussed more often and garnering more interest from both sexes, probably due to figures like Sheryl Sandberg and Marissa Meyer.

Are you involved in any organizations that help to promote female entrepreneurship

I am an advisor to Girls Who Code and am a frequent mentor, judge and speaker at various women’s conferences, competitions and hackathons, including Women 2.0 and Startup Weekend. My previous company, JumpThru, sent out a weekly newsletter called MyTechLetter, which focused on female founders, female early-stage investors and women in technology.

Do you feel investors have a different mindset when it comes to investing in a woman-run company? For example, does the work/life balance issue come up.

Investors tend to invest in products and services that they understand and are familiar with. Thus, more than the work/life balance issue, investors need to consider the types of companies that women found and run as they are naturally different from the types of companies men would create.

Do you think that women in top roles at major tech companies are scrutinized more closely than their male counterparts? 

I don’t know if they are scrutinized more closely but they are in the minority so are more noticeable.

Where do you and your company fit into the ecosystem?

Plum Alley is the destination site where women entrepreneurs can get funding, advice from experts, and the opportunity to sell products and tell their story. Currently an e-commerce platform, Plum Alley will go live this Fall with new features including crowdfunding, where women can submit projects to receive funding. This funding platform is not equity-based and can be used for just about any project that has merit in the arts, business, or that can improve the world.

Plum Alley came about because I saw that women were creating amazing products and companies, but weren’t getting enough attention for their outstanding contributions. There is so much commentary that women aren’t in tech, women don’t take risks. I just didn’t see that at all and I felt there needed to be a dedicated site and voice championing for women’s innovations and accomplishments. The expansion of Plum Alley’s offerings are a direct result from meeting so many women and hearing their needs of raising funds and obtaining expert advice.


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