Women in NYC Tech: Chaya Cooper of Click2Fit - AlleyWatch

Women in NYC Tech: Chaya Cooper of Click2Fit


Are you a woman in NYC Tech and interested in participating in this series? Make sure to read the whole article…

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 women in tech 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.

Today we speak with Chaya Cooper, two-time entrepreneur and current CPO at Click2Fit. As early as 1999, Chaya has been involved with tech and the user experience within clothing personalization. With experience as a developer, consulting and founding two startups, Chaya brings her strong work ethic to her company, never settling for anything less than perfect. A member of Dreamers // Doers, Chaya has made her mark in the NYC ecosystem and has no plans of slowing down. Overall Chaya plans to match you with the most suitable clothing as well as foster an environment in NYC that is most suitable for female entrepreneurs.

Chaya Cooper

Chaya Cooper

What’s your background and how did you develop your career as a female entrepreneur in the NYC tech ecosystem?

I started out in fashion tech 18 years ago, when my experience on Bloomingdale’s buying team, combined with my own difficulties shopping and a desire to make it easy for women to find clothing that makes them look and feel great, inspired me to launch my first company, and pioneer the concept of mass-customizing clothing by body type. That experience led me to realize that many of the consumers’ pain points and industry inefficiencies could be addressed by making it easier for shoppers to find the needle in the haystack. And the idea for Click2Fit was born: an automated expert system that enables retailers to accurately recommend clothing you’ll love, that flatters and fits.

I am nothing if not persistent. When leading experts told me that the technology wasn’t feasible, I tapped into my long-forgotten CS classes and designed the software’s architecture and convinced them otherwise. And when I kept running up against the Catch-22 of being unable to build AI software this complex without the funding to hire a tech team, I started learning everything I needed to know in order to build it myself — from artificial intelligence, cognitive neuroscience and physics, to creating the algorithms and developing the software. Fast forward several years later, and Click2Fit’s about to start beta testing its expert recommendation software, and I became a full-fledged software engineer along the way.

It wasn’t all that long ago that the NYC tech startup scene had such a small presence that the most common reaction to that phrase would have been, “What New York tech startup scene?” In fact, when working on a women’s tech incubator in early 2011 with Bonin Bough, convincing stakeholders of NYC’s value proposition for tech startups was far more challenging than getting them to back female founders. But as a result, it created something really wonderful: an unmistakable feeling of community and interconnectedness, where people really go out of their way to help each other and the community, and a sense of shared purpose, accomplishment and pride. Those sentiments are magnified many times over in the emerging community of female founders, where I think a great many of us feel a sense of responsibility to help pave and ease the way for others.

What are the advantages of being a woman in tech?

We are incredibly persistent, unconventional, untraditional, out-of-the-box thinkers, who’ve gotten there the hard way, and those of us who are programmers are more likely to be largely self-taught and to have acquired a wealth of experience and skills in other sectors before getting into tech. Women didn’t get into tech because it was the obvious choice or easy career path — we have all experienced gender bias, isolation and intimidation, repeatedly, and we are here in spite of it. And though the data shows that men are more confident, women are more competent.

You automatically become a member of an incredibly supportive community of women who really look out for you, open doors, and share and create opportunities, and with the recent explosion of amazing resources and support, and a concerted effort to effect change, there’s never been a better time to be a woman in tech.

What can be done to further promote female entrepreneurs and women in tech in New York?

It is important to recognize that many of the conventional means used for assessing people and opportunities in the tech and investment community tap into the very areas where women generally differ significantly from the stereotypical male founder or techie.

Find ways to allow us to shine that play to women’s strengths and communication styles, recognize women often respond differently when challenged, and compensate for gender bias. Account for women’s tendency to over-prepare, under promote, and undersell themselves, and being far more likely to err on the side of caution when pitching potential investors, partners or team members.

Tech companies led by women are more capital-efficient and achieve, on average, a 35% higher ROI than firms led by men, and, when venture-backed, bring in 12% higher revenue than male-owned tech companies, according to a study by the Kauffman Foundation. Yet, despite the fact that female founders are actually a far better investment opportunity, the greatest challenge women face when starting and growing their companies is less access to funds. Women start companies with 50% less capital than their male counterparts, and female-founded Inc. 500|5000 firms are dramatically less likely to raise equity financing from angels and VCs than male-founded companies (14.4% versus 3.6%). While the discrepancy in venture funding for startups in NYC with mixed-gender founding teams versus all teams has been shrinking since 2014 (decreasing from -23.31% to -6.59%), startup with all female-founded teams are actually doing far worse (increasing from -6.74% to -32.85%). Furthermore, these metrics only account for women who have successfully raised capital, which women do with far less frequency than men.

In addition, the second greatest obstacle for women entrepreneurs is they have a significantly greater difficulty finding appropriate co-founders. Similarly, women are less likely to have some of the technical, fundraising, or business development skill sets currently expected on founding teams. Think outside the current tech innovation model and recognize that few founders excel at the intersection of tasks expected of founders, and that most startups would in fact be far better served by founders playing to their strengths and hiring the requisite skill set.

What is diversity to you and do you see it evolving in tech?

To me, it’s when a company reflects the diversity of its target market and/or the country’s workforce as a whole — across all skillsets, departments, and levels.

In many ways the tech sector has evolved dramatically since the late 90s, when I rarely met other women in technical or leadership positions at tech companies, and the female programmers I knew all worked at financial firms, corporate research labs, or in academia.

But as wonderful as it is to no longer be the only woman in the room, the tech sector still lags far behind nearly every other industry and professional occupation in terms of diversity. Women account for only 35% of overall employees in the tech sector, 23% of all managers and executives, and 12% of software developers, and its workforce skews significantly more White, Asian, and foreign-born, than the overall professional workforce. In fact, there are actually more guest workers (non-U.S. citizens with H-1B or L1 visas) employed as software developers than women. Moreover, a 2015 LinkedIn study of software engineers across a dozen industry groups found that the tech industry employed a far smaller percentage of female software engineers than other industries.

More importantly, my experience within the NYC startup ecosystem differs dramatically from that of IT as a whole, where the proportion of women working in computer science-related professions has actually been declining for nearly three decades, from 31% in 1991 to 25% in 2015. Amongst programmers, the decline has been even more stark — the percentage of female software developers across all sectors has plummeted from 42% in 1987 to just 18% in 2015.

Contrary to popular opinion, the primary culprit hasn’t been a pipeline problem — it’s been a retention issue. Despite most women in the tech sector genuinely enjoying their work, the industry’s work culture and gender bias are the reason for women’s quit rate being more than double that of their male counterparts. Moreover, those two factors are directly responsible for 52% of female technologists abandoning the field during that time, and a third of women saying that they are likely to leave the industry within a year. Though much attention and resources have been directed at improving diversity, there is ample evidence suggesting there was often far more focus on window-dressing than on actual change.

I have, however, noticed a massive shift during the past two years — in large part due to a growing recognition of diversity’s impact on the bottom line — and I am increasingly hopeful that the slight uptick in last year’s diversity numbers reflects change underway.

Why do you think it’s important that women retain, grow, and develop into senior roles within their organizations?

There is a dire talent shortage in the tech sector, and the rapid pace of industry expansion and finite pool of H-1B visas mean that the problem is only going to get worse — or alternatively, can be easily solved by stemming the brain drain of women in tech. And the key to creating an environment where women want to work is cultivating more talented women at every level in the company.

There is also ample evidence of the positive effect diversity has on overall performance. A 2014 MIT study found that a more even gender split leads to happier and more productive employees, and could increase revenue by 41%. Additionally, a solid body of research demonstrates the enhanced performance outcomes and benefits brought about by diverse work teams (in particular computing teams), and diverse teams often outperform teams composed of the very best individuals, because this diversity of perspective and problem-solving approach trumps individual ability. Moreover, a 2011 study published in Harvard Business Review showed that women outscore men in 12 of the 16 competencies that go into outstanding leadership, and three of the areas where they really shine — taking initiative, driving for results, and self-development — are attributed to the still-tenuous position they feel themselves to be in the workplace and their need to work harder than men to prove themselves.

More importantly, the current lack of diversity means that most technology is being created and guided by a relatively homogeneous group of people, and as a result, technology is rife with flawed inherent assumptions and biases that are baked in from the start. Moreover, given that more than half of the users of technology products and websites are women, and women’s choices impact up to 85% of purchasing decisions, it stands to reason that it is in a company’s best interest have an appropriate ratio of women involved at every step of the way.

How do you see the future of teams and interactions in a diverse environment and what implications will this have?

I think there is a growing awareness of the fact that everyone is (at least) a little bit biased, and as a result a growing use of methods and tools to help mitigate bias. As companies become more transparent with their data and share what works and doesn’t work, I believe that most sectors will start becoming far less homogenous.

I think the pace and success of this change will be aided by companies devoting resources towards helping all sides acquire the skills and tools to affectively overcome biases, and that forward-thinking companies will recognize the importance of expanding this thinking well beyond their own ranks to affect change throughout their ecosystem.

Chaya Cooper click2fit.001

How can women rise in the ecosystem and what are the unseen barriers?

There is a host of research now validating what women have long suspected: We are consistently interrupted and talked over, viewed as less authoritative, and our ideas are scrutinized more harshly, co-opted, or fizzle out, at a far greater rate than men — simply by virtue of our voice, speech patterns, and demeanor. And often the very behaviors that cause men to be perceived as more confident, have the exact opposite effect for women. Or as Sheryl Sandberg and Adam Grant put it, the perils of “speaking while female.”

Gender bias extends well beyond that, and two-thirds of women in STEM report having their expertise consistently questioned, their success regularly discounted, and having to prove themselves over and over. As a female technical founder, I still find myself having to slip in a few credibility-garnering statements to avoid facing the uphill battle of proving that I might actually understand the products I’d invented, and have more than a passing familiarity of the market. Which I have to admit has been a stark, and at times demoralizing, contrast to the reasonable amount of credibility and market expertise generally conferred upon me rather effortlessly, and one which is largely due to social cues and language patterns.

It’s not only men who exhibit gender bias. Much of our biases stem from decades of history being filtered through the same type of unconscious cognitive biases and heuristics which allow us to rapidly process input and make decisions; and as a result, women are often guilty of it too. I was having lunch with a bright, soft-spoken female developer last winter when I found myself fighting back against my own gender bias. I realized that I so rarely meet female backend developers in NYC, that I automatically categorize technical women I meet a certain way, and it took a good deal of both information and effort on my part for my mind to accept that she might be the exception to the rule. We had a good laugh about it and a wonderful discussion about ways to short-circuit the cognitive hoops I’d had to jump through, and perhaps more importantly, it has helped me be a lot more understanding of it when I am the one on the receiving end of it, and a new-found appreciation for the need for women to be a more visible presence.

These nuanced biases affect the feedback loop significantly — studies show that men are twice as likely as women to be hired, promoted, or recognized for their accomplishments when the only measurable difference is gender, and investors routinely choose to invest in male founders over female founders. Additionally, context matters. A series of studies on diversity hiring published in Harvard Business Review in 2016 found that when the short list included only one minority candidate, their odds of being hired were zero, but when at least two such candidates were included, the odds of hiring a minority were 194 times greater.

Many of the barriers today are so subtle that it is often hard for women to even acknowledge them at the time, let alone speak up about them, but when they happen day after day, there is an effect nonetheless. Knowledge of the issues is an important step towards empowering women, and enables them to recognize it in the moment, and either let it roll off their backs or respond accordingly. Female mentors and supportive communities of women are also an invaluable resource for learning how to navigate these issues (and in fact, I’d estimate that at least half of the time I spend mentoring women relates to this in some way). In addition, while confidence doesn’t eliminate the problem, it does mitigate it; as does acting “as if,” by practicing assertive body language and speaking authoritatively.

Finally, few people achieve professional success without mentors, sponsors, and role models; women are less likely to have these relationships altogether, and when they do, subtle biases often cause them to be far less effective. It is therefore not surprising to find significant overlap between the benefits ascribed to those relationships, and women’s primary obstacles; namely, visibility with the right people at the right time; leaders championing on their behalf, and providing public and private endorsements; guidance navigating unwritten rules; increased confidence and competence; and assistance networking and cultivating relationships. In fact, technical women identify a lack of mentorship or sponsorship as one of the key barriers to their retention and advancement.

Please tell us about a few organizations that you are involved with or respect that are promoting women in tech.

My top three are: Dreamers // Doers, a high impact community of trailblazing, entrepreneurial women (and of which I am a proud founding member); Women Who Tech, which brings together women tech change makers, disruptors, and startup entrepreneurs who are transforming the world and inspiring change; and Y Combinator’s Female Founders Conference. All three groups actively create opportunities for women in tech and female founders, including some of the most effective (and enjoyable) events around; advocate tirelessly on their behalf; and have vibrant online communities which I regularly participate in.

I can honestly say that I’d never realized just how isolating my experience had been up until groups like these were formed, and I am blown away almost daily by the incredible women I have the honor of co-mentoring, supporting, commiserating with, and collaborating with.

What can men do to participate in this discussion?

Use your gender to your advantage to advocate in ways that women can’t.

When you notice a lack of diversity or lower participation rate in a group of speakers, founders, team members, or job candidates, question the efforts that were made to include suitable women and underrepresented minorities.

Know that we’re all a little bit sexist — and correct for it. Practice bystander intervention and stop interrupters. When women are speaking, back them up by visibly showing your interest. When women have a good idea, draw attention to it by publicly supporting it.

Make a conscious effort to be a catalyst for change by increasing both the quality and quantity of your mentoring and sponsoring relationships with women. Form sponsoring relationships to help make them and their accomplishments visible with the right people at the right time, champion on their behalf, and provide public and private endorsements. Form mentoring relationships to help them navigate unwritten rules; increase their confidence, competence, and networking opportunities; and expose them to opportunities which enable learning effective presentation and negotiation skills by example. Recognize that success fosters the confidence that breeds more success, and help create opportunities for women to succeed.


The team at AlleyWatch believes it’s important to have an inclusive discussion around the challenges facing women in tech along with highlighting the work of the female entrepreneurs that have made NYC one of the best places for women in tech according to some recent studies. That’s why we are running this series that showcases women in tech in New York.

If you are a female founder in NYC working in tech and interested in participating in the series please visit this link or click on the image above.

Please feel free to pass this on to any women in NYC that you feel should be considered for the series. Thank you.

About the author: AlleyWatch

AlleyWatch is the destination for startup news; opinions and reviews; investment and product information; events reported, experienced, seen, heard and overheard here in New York. But it’s who we are that makes us different: we’re the writers and the entrepreneurs; the investors and the mentors; the lawyers and the marketers; the realtors and the recruiters – the people who work in the industry.

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