#CyberMentoringMonday and Advocating for Others

Tanya Teaching

I have run an informal mentoring program, every single Monday, since 2018. It’s very simple; I use the hashtag #CyberMentoringMonday on Twitter and Mastadon, to try to help people find each other. I don’t pair people myself (it turns out I am an awful matchmaker), people use the thread to announce they are looking for a mentor or offering mentoring, and then the rest is up to them. Since starting it there have been countless amazing human beings who have offered their time, expertise, and assistance to those who want to join our field, all for free. I don’t run it by myself anymore, it’s bigger than me now, several other people run it with me! Although most of the ‘action’ happens in direct/private messages, there is more happening than it may appear.

This is me! Wearing glasses! And smiling!

Anyone can help with #CyberMentoringMonday, just use the hashtag to help people find each other!

This small mentoring program has helped thousands of people find each other over the years. It has resulted in jobs, friendships, starting companies together, and more. Since I have been running this program for a long time, people often ask me how to be a good mentor. I would love to tell you all that I know the answer and that applies for every situation, but we all know one size does not fit all. That said, I will tell you what has worked for me, and that is advocacy. Advocating for the people I am mentoring, by sending them as many opportunities as I can.

Mentoring can take many forms, but the format that has always worked best for me (receiving and giving) is to create opportunities (which is part of advocacy!). I have had my professional mentors do all sorts of amazing things for me, such as: standing on stage with me when I gave my first conference talk so I wouldn’t have a nervous meltdown, telling a hiring manager they wouldn’t accept the job unless I was hired too, introducing me to people who wanted to hire me/buy my services and/or products, helping me navigate having people stalk me online, and more. To say I am incredibly grateful to my mentors would be an understatement. 

Anyone can help participate in #CyberMentoringMonday, as a mentor and/or as a mentee. And it’s freeeeeeee!

In attempts to ‘even the scales’ and ‘pay it forward’, I do my best to advocate for others whenever possible, especially those from groups that are underrepresented in tech (such as women, disabled people, people of colour, etc.). Since I fit into more than one of these groups, I do my best to lift us all up, not just myself.

I am of the opinion that if I’m going to work my butt off to open the door for myself, it’s not that much more work to hold it open for one more person. Seriously, it’s really not that much extra work. If I manage to get myself invited to be a guest on a podcast, it takes very little effort to put myself out there a tiny bit more and say “Hey, are you looking for more guests? Because I have a list of a bunch of other women security experts, who are less well known that me, but who are equally knowledgeable and awesome. Want some intros?” The worst they can do is say no. And I have to tell you, most of them say “Hell yeah, send me that list!”

You have privilege and power. And you can use it to help others.

– Me

I’m going to tell you about some of the ways that I use my power to help others, in hopes that YOU think of ways that you can share your power and/or privilege with others.

Examples Advocating for Others:

Example 1: I wrote an essay to explain to a conference why one of my mentees deserved a diversity grant. She has worked SO HARD to teach herself and change careers. She won the grant because of her hard work, but my essay helped. It took me 30 minutes, and she benefited.

Example 2: I brainstormed talk ideas with a mentee, then she built an amazing technical proof of concept. I asked a conference that I was keynoting to book her, even though she’d never spoken before. She was AMAZING! Out of this world! I knew she would be good, but she was 10 times better than I would have dared to hope for. I’m so proud of her!!!

Example 3: When I’m invited to speak somewhere but cannot make it, I ask if they would like me to recommend someone else. I have a list of people who are not as well-known as I am, but who are amazing. I always recommend one of them to take my place. I advocate for them.

Making just one introduction can change a person’s entire career.

– SheHacksPurple

Example 4: I asked a friend to let one of my mentees into his very expensive training for free, and he said yes. I let her stay in my hotel room with me so she could afford the trip. It cost me one favour and sharing my room, to give her a huge leg up for her career.

I use the power and privileges of my career and whatever job I’m currently doing to help others, and you can too. You may not even realize how much power you have until you start helping someone.

Sometimes it’s recommending or loaning someone the right book. Sometimes it’s about letting them have a place in your training, workshop, talk, or conference for free. It’s giving someone a lift to an event they wouldn’t be able to get to themselves. Sometimes it’s helping them when they are stuck at work on a technical problem and you give them the answer. Maybe you will introduce them to the person who will hire them some day. It’s about helping however you can. You don’t need to put yourself out very much, to make a big difference in someone else’s life. And it’s definitely worth it!

I have a secret for you all: helping others FEELS GOOD. And the more often you do it, the more you will want to do it again.

I hope to see some of y’all at the next #CyberMentoringMonday!

Jobs in Information Security (InfoSec)

Image by Henry Jiang of Oppenheimer & Co.

Almost all of the people who respond to my #CyberMentoringMonday tweets each week say that they want to “get into InfoSec” or “become a Penetration Tester”; they rarely choose any other jobs or are more specific than that. I believe the reason for this is that they are not aware of all the different areas within the field of Information Security (InfoSec for short, and “Cyber” for those outside of our industry). I can sympathize; I was in the same position when I joined. I knew three Penetration Testers and lots of Risk Analysts and I had no clue that there were several other areas that may interest me or even existed. I knew I didn’t want to be a Risk Analyst, so I thought the only other option was PenTester. Now I know that is not true at all. This blog post will detail several other areas within the field of Information Security in hopes that newcomers to our field can find their niche more easily. It will not be exhaustive, but I’ll do my best

Image by Henry Jiang of Oppenheimer & Co.

The above image shows 8 different potential areas within the field of Information Security according to the author, Henry Jiang; Governance, Risk, Career Development, User Education, Standards, Threat Intelligence, Security Architecture and Security Operations.

Since I come from the software development side of IT, and have done almost exclusively coding, my view is going to be extremely biased. With that in mind, the first area you may want to consider is Application Security (AppSec); any and all work towards ensuring that software is secure. This is the field that I work in, so it will have the most detail. There are all sorts of jobs within this field, but the most well-known is the web app pentester (sometimes called an ethical hacker); a person who does security testing on software. Such a person is often a consultant, but can also work in large companies. They test one system, intensively, perform a lot of manual testing, and then move on.

Jobs in Application Security:

  • Application Security Engineer — you do a mix of all the things listed under AppSec and you are generally a full-time employee. This includes making customer tools, launching a security champion program, writing guidelines, and anything else that will help ensure the security of your organization’s apps. I personally consider this the sweet spot, as I get to do changing and interesting work, and see the security posture improve over time. It is, however, usually a more senior role.
  • Threat Modeller, working with developers, business representatives and the security team (that’s you in this scenario) to find and document potential threats to your software, then create plans to test for and fix the issues.
  • Vulnerability Assessment: running lots of scans, all the time, of everything. You can scan the network too. Ideally, you will do more than this, to assess the security of the systems in your care, but it depends on where you work. This position is often an employee position and you tend to have prolonged relationships with the systems and teams you assess.
  • Vulnerability Management: Keeping Track of the vulnerabilities that all the tools and people find, reporting to management about it, and planning from a higher level. For instance; attempting to wipe out an entire bug class, implementing new tools because you see a deficiency, resource planning, etc. This is an employee position usually, and often a manager role or team lead.
  • Secure Code Reviewer: reading lots of code, using SAST (static application security testing) tools and SCA (Software Composition Analysis — are our 3rd party components secure?), finding vulnerabilities in written code and helping developers fix it.
  • DevSecOps Engineer: an AppSec engineer working in a DevOps environment. Same goal, different tactics. Adding security checks to pipelines, figuring out how to secure containers and anything else your DevOps engineers are up to.
  • Developer Education: this is usually a consultant role, but sometimes for large companies, someone can do this full time. The person teachers the developers to write secure code, the architects to design secure apps, threat modelling, and any other topic they can think of that will help ensure their mandate (secure apps). This person is likely also to training the security champions.
  • Governance: writing policies, guidelines, standards, etc, to ensure your apps are secure. This job is usually someone that does all the governance stuff for your org and the person is working with the AppSec team to get the details right, OR this person is likely a consultant because this is not an activity that needs to be re-done constantly.
  • Incident Response: this area includes jobs as an incident manager (you boss everyone around and make sure the incident goes as smoothly as possible), and investigations (Forensics/DFIR). Investigating incidents related to insecure software is a topic I personally find thrilling; detective work is exciting! But with the stress it causes, it’s not for everyone.
  • Security Testing: often called Penetration Testing, sometimes called Red Teaming, sometimes not officially recognized as a job because management isn’t “ready” to admit they need this yet. This person tests the software (and sometimes networks) to ensure they are secure. This includes manual testing, using lots of tools, and trying to break things without causing a huge mess.
  • Design Review: This is called a “Security Architect” but AppSec folks are often asked to review designs for potential security flaws. If asked, say yes! It’s super fun and always educational. Bonus; it’s a good way to build trust between security and the developers.
  • In AppSec you will also be asked to do a range of other things because that’s how life is. Potential asks; install this giant AppSec tool and figure out how it works, create a proof of concept for an exploit to show everyone that it is/is not a problem, create a proof of value with a new AppSec tool we are considering acquiring, get all the developers to log their apps like ‘so’ in order for the SIEM can read the results, research how to do something securely when you have no idea how to do that thing at all, etc. As I said, it’s super fun!
ISACA Victoria, Dec 2019

Security Architect (apps, cloud, network): Security architects ensure that designs are secure. This can mean reviewing a deployment, network or application design, adding recommendations, or even creating the design themselves from scratch. This tends to be a more senior role.

SOC Analyst/Threat Hunter: SOC analysts interpret output from the monitoring tools to try to tell if something bad is happening, while threat hunters go looking for trouble. This is mostly network-based, and I’m not good at networks, otherwise, I would have been all over this when I moved into security. The idea of threat hunting (using data and patterns to spot problems), is very appealing to my metric-adoring brain.  Note: SOC Analyst is a junior or intermediate position and threat hunter is not a junior position, but if you want to get into InfoSec they are basically always hiring for SOC Analysts, at almost every company.

Risk Analyst: Evaluate systems to identify and measure risk to the business, then offer recommendations on how to mitigate or when to accept the risks. This tends to be coupled closely with Compliance, and Auditing, which I won’t describe here because I am shamefully under-educated in this area.

Security Policy Writer: Writing policies about security, such as how long network passwords need to be, that all public-facing web apps must be available via HTTPS, and that only TLS 1.2 and higher are acceptable on your network. Deciding, writing, socializing and enforcing these policies are all part of this role.

Malware Analyst/Reverse Engineer: Someone needs to look at malware and figure out how it works, and sometimes people need to write exploits (for legitimate reasons, such as to prove that something is indeed vulnerable, or… You need to ask them). If you enjoy puzzles and really low-level programming (such as ARM, assembler, etc), this job might be for you. But be careful; playing with malware at home is dangerous.

Chief Information Security Officer (CISO or CSO): ‘The boss” of security. This person (hopefully) has a seat at the executive table, directs all security aspects for a company, and is the person held responsible, for better or for worse. If you enjoy running programs, managing things from a high level, and making a big difference, this might be a role for you.

Blue Team/Defender/Security Engineer (enterprise security/implements security tools): The people that keep us safe! These people install tools, run the tools, monitor, patch, and freak out when people download and install things to their desktops without asking. They perform security operations, making sure all the things happen. While those in the SOC (Security operations centre), monitor everything that’s happening and respond when there are problems.

There are many, many, many jobs within the field of Information Security, please feel free to list some of the ones that I missed in the comments below. I hope this information helps more of you join our industry because we need all the help we can get!

My Career Story

Me, smiling

I started coding at 17 years old, and it was love at first sight.

I got great marks in all of my classes in high school, but loved computer science because in every class, I could “make something out of nothing.” Computer science runs deep in my family as almost all of my aunts and uncles are computer scientists, and my cousins are engineers, scientists and programmers. When I announced that I wanted to go to college for computer science my family responded with “what else would you take?” It wasn’t until years after working in tech that I realized that this is not an experience that most young women share.

I landed my first job in tech at age 18, and haven’t stopped since, despite several career setbacks, harassment and toxic work environments. I realize this might not seem very encouraging, but I have to tell you; things in tech have really improved. I’ve had the fortune of work experience in a variety of different situations both in computer science and in my other passion, music. Both careers taught me the value of collaborating with others, confronting differences, and taking constructive criticism well. It’s also given me the benefit of becoming more resilient when it comes to unpleasant situations or less-than-constructive comments made in the workplace.

For many years, I was a programmer by day and a musician at night. My successful music career allowed me to play in countless venues and bars around town, and it taught me many lessons that have since turned out to be very helpful in tech, such as how to handle hecklers, how to capture the attention of a drunk and belligerent crowd, and what the best way to throw someone off a stage is. As you can imagine, there were challenges to being a young 20-something woman in a hardcore punk band.

Later in my career I met an ethical hacker who was also in a band and we became friends. He spent the next 1.5 years convincing me to join him as his apprentice and learn how to hack. I became fascinated with the security of software, I wanted to know everything. I joined my local OWASP chapter and almost immediately became a chapter leader, which helped me greatly since I had the chance to invite experts on topics that I was interested in to come speak for us. I also met my next 3 professional mentors though OWASP, who taught me even more. OWASP is an incredibly supportive and amazing community, I strongly recommend that everyone joins their local chapter.

OWASP Montreal, I drove there with my mom to speak at lunch time. I missed a day of work for it.

At this point in my career I felt like I had a thirst for knowledge that could not be quenched. Although I managed to switch over from software development to a full time security job, I was frustrated that there was no budget for me to go on the types of advanced training that I was interested in. Then one of my professional mentors convinced me to speak at a conference, and they let me in FOR FREE.

For the next 2 years, I spoke at meetups and local events, taught myself as much as I could, and worked in application security helping developers make more secure apps. I loved it, but I kept striving for more. I wanted to do more modern types of application security, and I realized that the organizations I worked for were not very modern, and resistant to change. I found that my drive and ambition was difficult for certain managers, and it became a point of friction for me in the workplace.

Then I broke through from meetups into speaking at conferences. I honestly couldn’t believe it when I received the email saying that I had been accepted to speak at AppSec EU, the international OWASP conference. I discovered that all of my musical stage performance skills transferred over and with all of my practice at meetups that I had become good at public speaking. After AppSec EU, I had invitations to speak all over the world. As conferences started sending me plane tickets, I took time off work and went off to learn for free. I realized that a career shift was necessary. I knew that I had something to offer to the right employer, but I wasn’t quite sure what that would be… Then Microsoft reached out to me.

A Microsoft representative said that he had heard about me, and wanted to interview me for a “Developer Advocate” position. I had no idea at that point that “developer relations” was a job, and when he described what the job would be I said “I already do that, for free.” It took him about 20 minutes to convince me that he was not kidding, this was a real job, and he was actually from Microsoft. Before I knew it, I was traveling the planet, learning about cloud security, working with absolutely brilliant people and so much more. All the while I was *getting paid* to do it! Talk about a dream!

During my many years traveling and talking to the community, I learned a lot about my industry, both good and bad. I learned that software developers had a lot of aches and pains in regards to security that I had also felt when I was a developer, and especially during my work in incident response and AppSec. My goal in being a developer and cloud advocate was to help push the industry forward, and to help people create more secure software, everywhere. During this time I founded the #CyberMentoringMonday online initiative and the WoSEC (Women of Security) organization, released countless articles, videos and podcasts, and spoke regularly at security events. Although I definitely felt I was helping many people in my industry, I felt like I could do even more. I also felt the constant travel was extremely exciting, but also exhausting and perhaps not the most efficient way to help the most people. I wanted to figure out how to make a bigger difference, and ’scale’ myself in a more effective manner.

With that in mind, I started to devise a plan; focus my efforts in a more concise way in order to deliver more impact. Do fewer things, but do those things in a very big way. I decided to choose two big goals; to write a book and start my own company. And I decided I would just go for it, even if it was scary.

I realized at this point that I was going to have to leave Microsoft to pursue my new career goals. I decided to start my own online training academy, We Hack Purple. We have a podcast, community and courses, it’s a dream come true!

I am also in the process of writing my first book! It’s an intro to AppSec, “Alice and Bob Learn Application Security”, and I’m excited to share it with the community at large when it’s ready. Even though I am at the very beginning of both of these adventures, you better believe I plan to knock them out of the park! ** Alice and Bob Learn AppSec is now available worldwide!

If I can offer advice to you it is this: if you want it, go get it. Don’t let anyone tell you that you can’t reach greatness; you can, you just need to be prepared to work like you’ve never worked before. The Information Security industry needs all the help it can get, and we definitely need you. Yes you, the person reading this right now. Please join us, and help us make the world a better and more secure place.

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