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Sexism And Career Tactics

By August 2, 2016February 1st, 2019No Comments
J. Kelly Hoey - Build Your Dream Network

This post started as a result of a Tweet back in 2014.

Is this perspective congruent with your experience?

The experience being referred to was whether I like other women in / around / part of the tech and startup scene had experienced mistreatment of the overtly sexual kind.

The short answer is No.

But then again, I’m 48 and tech is not my first trip to the career rodeo. And having come to tech via commercial mortgage-backed securities, corporate restructurings and legal management aka the suffocating world of suits distained by many of those in tech, I’ve been there and experienced that. The mistreatment of women of tech is frustrating as it is dull bull#t in a “Really! This industry was supposed to be different than the established corporate world those in tech rejected!” way. It seems that the behaviors that hold women back have crossed industry lines, the only difference being that the misogyny is now served up with warm beer and cold pizza versus the red wine and rare steak Wall Street way.

In both scenarios, women rarely talk about it or name names. Talking about it is taboo, but is not talking about it, weakness?

Not talking about “it” kept my legal career moving forward in Toronto. My greatest career mentor was also a sexual predator and harasser of Hannibal Lecter proportions. A true Dr. Jekyll and Mr. Hyde: Brilliant attorney, thoughtful mentor, alcoholic and womanizer. I was the beneficiary of my mentor’s insights, privilege and industry insider access until I wasn’t. Want the key to corporate kingdom….I did but not at that blow-me price.

I did the only thing I could do to keep my life from falling apart: I put in the long associate billable hours on a major corporate career transformative case, silently took the abuse, recorded all of the abusive voicemails with my Dictaphone (sending the tapes to a friend for security) and desperately hoped I’d find another job within Toronto’s protective, close legal community. When the big case ended I suffered the humiliation of a “your skills are not up to par” demotion and after many months, I did land that next associate job — at a bigger, much more prestigious law firm.

My mentor landed in rehab.

I was rewarded for my silence with entrance to the old boys club. A short while after my mentor landed in rehab again (no, this was not his first time being locked out of his office and forcibly threatened into rehab), I found myself once again having “beers with the boys” (aka the partners at my new firm) when one asked “did he do this to you?”. “He” was not the current topic of conversation and the person asking the question was standing next me, looking straight ahead. A smart lawyer, he only asked the questions he knew the answer to. “Yes” was my simple reply, which was followed by a “we’re sorry” delivered in the firm grasp on the shoulder guy way. My career in Toronto moved upward, I was one of the boys.

Then I moved to New York. The year was 1998, the CMBS heyday and I was now a transaction junkie attorney. I loved working on deals and my CMBS clients delivered the deals in rapid succession. How could I work with “them” I was frequently asked. “Them” were my frat boy clients. It was easy. They were boys in the mold of Ocean’s Eleven — trouble mixed with high octane deal-making. I let them search porn on my computer because when you’re going to the printers with a camera ready copy of your prospectus, it sure is handy to have the client close by at 3:00 am. Book the conference room over-looking the apartment where the female tenant entertains frequently? No problem — what better insurance for an on-time closing before the trading window closes for the day. And I was untouchable. I was their attorney, just one of the boys, dishing it out as thickly and letting it roll off my back.

It was great four-year run and I loved every billable hour client deal of it.

I changed careers in 2004, moving from being on the revenue generation side of the law firm ledger to the cost center side. As “management” half the job s justifying your existence on daily basis by delivering on your department’s mandate and the other half is constantly seeking more resources, some budget, any help.. This constant maneuvering is particularly true when the role is “attorney development”. What better development than working on client matter? True (plus an associate billing hours pays not only their salary but also overhead, like me), but….not everything about being a great lawyer is learned on a due diligence project. On the subject of budgets, don’t even start me down path of getting any funding for a firm’s Women’s Initiative. It was a relentless budget battle, and one I was determined to win with every advantage I had — including program results.

“Nice shoes” read the email.

It was 9:30 pm and I was stepping off the elevator, just leaving the office. They were not simply nice shoes, they are stunning black suede Alaia pumps. A wry smile crossed my face as I typed “Thank You”. The sender was very senior management at the firm and not based in New York City. I didn’t know he was in New York that day but I now knew his Achilles Heel. I chose my shoes very carefully from that day forward as this man had incredible influence over my department’s budget. Did I feel compromised? Hell no! Using the information got me more of what I needed to be successful in my role and to deliver ground-breaking (in the law firm context) training / retreats / advancement initiatives. A trip to HR would not have enabled me to ever accomplish any portion of that. Prior traditional and path generally taken routes to get more resources had fallen on deaf senior law firm administration ears. Against my better judgment, I’d occasionally resorted to email tantrums born out of sheer frustration and exhaustion. These had no effect nor did simply putting in long hours / doing good work. But I was having an impact: the programming I implemented was making a difference in the careers of many associates and to really get things done, I discovered that all I had to do was slip on a pair of heels.

“What kind of wine do you like?”

I’ve been propositioned, groped, sexted and yes, I’ve hauled partners out of bars filled with female associates and colleagues before they were slapped with sexual harassment lawsuits. Having a firm’s client try to “impress” you by ordering wine they are sure you’ll enjoy is mildly amusing when the $1600 bill arrives. Ok, rather amusing to me, the firm’s partners? not so much.

So what’s the point in sharing this? I chose to respond to unacceptable professional behavior in a way that worked for achieving what were then my career goals. It was a very tactical short-term choice to a hurdle in front of me. By hanging with the boys I’ve developed an affinity for cigars and tequila. I also picked up golf — because I needed to in order to be in the room where career-changing decisions were made. I put myself in a position of power when it came to making choices about my career by developing a strong network, being the expert in my field and banking a yes me fund. With these tactics I eliminated the fear of losing my job. Being fired would not have affected my life, financially or socially. Now in hindsight, if I’d run to HR, threatened to sue the firm, I may have banked a nice settlement and would be in a position to invest more in female tech founders than I am already doing but I wouldn’t have been able to continue to be an insider advocate for women in the law. By choosing a different tactic, I stayed on the inside and got things done.

So what of tech? I entered this industry as an angel investor, then as a co-founder of Women Innovate Mobile (WIM) Accelerator — a venture that was first and enthusiastically from start to finish supported by men in the tech community. WIM would not have occurred without the support of men in tech. I see myself more as an inexperienced peer of many of these men and at 48 I’m not in the target demographic for sexual predators. I’m not ignoring or over-looking the nonsense and mistreatment women in tech are enduring, instead like chess, I see your sexual move and plan my way around it / over it/ through it. I may by all appearance be playing the game by the rules, but I am choosing my moves and staying in this game in order to ultimately change the rules. Having my own resources also helps. My Yes Me Fund mentality may be why even as an investor I’m a vocal proponent of bootstrapping early stage ventures and of founders owning their startups.

“I’ve got the scoop on him. Tell me what you need.”

“Him” is a very well known entrepreneur / investor based outside of NYC. The bliss of being late to the tech party is I frankly don’t know the storied history of many of these legends and am not easily impressed. Simply making money is not impressive — being Warren Buffet is, but I digress. I was interviewing “Him” at a conference in SF and my friend rightly assumed some past-life intelligence would be helpful in keeping the blustering self-aggrandizing interviewee in check.

“Tell me one thing”, I said. “How tall is he?”.


“I’ve got this.”

My shoes were of Kardashian heel proportions and yes, the interview lacked the usual investor ego antics.

J. Kelly Hoey

J. Kelly Hoey

J. Kelly Hoey is a problem solver who believes that most professional challenges—whether funding, landing a board position or getting a new job—are solved by tapping into networks.Kelly is a popular speaker on networking, community building and investing issues, especially as they relate to women, and has worked with the IEEE, PGA, Bank of America, Apple and countless others. Follow Kelly on Twitter @jkhoey and on Instagram @jkellyhoey and join the #BYDN community at

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