Ada Lovelace Day - hacker Alissa Knight on being a trans woman in a man's world

Cath Everett Profile picture for user catheverett October 12, 2021
To commemorate Ada Lovelace Day, we celebrate the achievements of Alissa Knight, a trans hacker who moved from the dark side into the light, became a serial entrepreneur, author and content creator, all before the age of 40.


Ada Lovelace Day, which is held each year on the second Tuesday of October, is a celebration of inspirational women in the field of science, technology, engineering and mathematics who have become role models in their own particular field.

One such person is Alissa Knight, a hacker who has moved from the dark side into the light, became a serial entrepreneur, author and content creator, all before hitting 40. After being born Eric Heinz, Alissa also transitioned in 2008 and, as such, has a unique perspective on the male-dominated cybersecurity sector in which she continues to make her living.

As to how Alissa got into the hacking world in the first place though, that happened at the tender age of 13. In time-honored fashion, after purchasing her first computer – a 486 SX/25 – Alissa became a member of the dial-up Bulletin Board System community of computer enthusiasts. From there, she migrated to using the Internet Relay Chat instant messaging system, which was where she met her first hackers. She explains the fascination:

At the time, there were no degrees in cybersecurity and YouTube didn’t exist, nor did SANS [Institute for cybersecurity training]. The idea of cybersecurity training wasn’t even a sparkle in people’s eyes. If you wanted to learn how to hack, you downloaded and played with exploits and tried to understand what they did. Hacking wasn’t as easy as it is now, where exploitation platforms have been turned into graphical user interfaces with point and click. Back then, you needed to know how to actually compile a .C source code file to make an exploit work.

Becoming a hacker – and more

So the impetus behind her becoming a hacker was that she had a curious mind, which meant in her case taking on the challenge of learning how applications worked before figuring out ways to “break them”. Alissa explains:

The psychological profile of a hacker, in my view, is someone that simply believes there’s a way through and around something. Someone who believes that anything made by humans can be broken by humans due to our inability to write perfect code clean of vulnerabilities. In a nutshell, a hacker, in my view, is simply a breaker. 

What made swap her black hat for a white one though was getting caught by law enforcement, aged 17, after hacking into a US government network. When the charges were dropped due to technical irregularities relating to her arrest, Alissa saw it as a second chance, enabling her to take her life in a new direction - not least as she had grown to hate “living in constant paranoia every time there was a knock at my door”.

And take her life in a new direction she did. Since those heady days, Alissa has worked in cyber-warfare for the US intelligence community, “defending networks against people like myself”. She has set up and sold two cybersecurity start-ups to private companies and is in the process of exiting a third.

Chair of managed security service provider, Brier & Thorn, Alissa is also involved in a host of advisory roles and has started her own venture capital fund. She is a member of the HackerOne ethical hacker community, runs a content creation and influencer marketing agency called Knight Ink, and has written a book, published by Wiley, entitled ‘Hacking Connected Cars: Tactics, Techniques, and Procedures’.  She is currently writing the screenplay for a TV series based on her life – and so the list goes on.

A woman in a man’s world

But as a trans woman, Alissa has also had the unique experience of working in the notoriously male-dominated cybersecurity industry as both male presenting and as a woman. Having done so, she has gained a much deeper understanding of the discrimination women face every day, including in salary terms. As Alissa explains:

I realize now, as a woman who has faced [the wage disparity] challenge in my career, no man can truly understand the impact it has on women and their families until they’ve been on the receiving end of it. Of course, they can think it’s wrong and support change, but they can’t truly understand its impact unless they’ve gone through it.

The situation “really became real” for her, however, when, post-transition, she attempted to negotiate the salary suggested in an offer letter:

I was given much higher offers for doing the same job as a man and was met with flippant reactions and shock simply for countering an offer. As a man, a counteroffer seemed to be received by hiring managers as expected, whereas after I transitioned, it was almost unexpected and, at times, met with disbelief that I wouldn’t just take what they were offering me. I have run into instances where a decision-maker for a client made sexual advancements towards me, thinking I’d trade sexual favors for a purchase order. This was something that never happened to me as a man. 

Lessons to be learned

As a result, Alissa believes it is imperative for employers to become aware of their unconscious biases in relation to hiring both women and trans employees. In fact, she advises making:

A conscious effort to try and hire a team made up of marginalised people, trying to perhaps have a 50/50 split between women/non-binary and men. Try your best to perform internal outreach to female employees in your company who might be interested in cybersecurity and train them for hiring within. A conscious effort needs to be made to hire more women into both these roles and the executive leadership team. Conferences should also make an effort to have an even split of men and women in their speaker line-ups.

After 21 years in the cybersecurity industry, however, one of the biggest lessons she has learned is not to wait on others to “spoon-feed” you in terms of either skills or knowhow but to grasp the nettle yourself. Another is the value of knowing your worth and refusing to take less. As Alissa concludes:

Don’t let anyone make you feel like you deserve less because you’re a woman. You deserve to be there just as much as your male colleagues. Most importantly, you have the capability to go further and faster than anyone else if you remind yourself you can do anything you want. You just have to put the work in to get there. Be the first one in and last one to leave.

One last lesson: 

I’ve learned that I’ll never be done learning, and the greatest regret I’ll ever have is having not tried.

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