Mentorship and career growth in cybersecurity | Guest Anneka Gupta

[00:00:00] Chris Sienko: Today on CyberWork, Anika Gupta of Rubrik joins us to talk STEM, science, technology, engineering, mathematics, the journey of students into the workforce, and the process of going from learning how to learn to learning how to work and thrive in the cyber security industry.

try to get to the heart of the issue, knowing that you'll never understand an issue a hundred percent, the goal is to always get deeper and deeper into understanding what that issue is, because once you can understand a problem, you can solve it.

Anika will give you a ton of great tips and strategies for more diverse hiring 

if you only try to look for people that have done it before, you're going to lose a perspective of looking at things radically differently and questioning the status quo.

making yourself seen and conveying your passion in your resume and interview, 

in a role, they have their bullets and they're like, I launched this, I did this, but they don't actually show what were the results that they drove. 

And offer some no nonsense first steps you can take to be an expert at networking.

coming up with, like, your problem and then asking someone for help, it becomes very. Easy for someone to say, yeah, okay, I can help you with this. Like, let's have coffee and let's talk about it. 

There is an art to being both a good mentor and a good mentee, and today you'll learn all of these things on this episode of Cyberwork. 

The IT and cybersecurity job market is thriving. The Bureau of Labor Statistics predicts 377, 500 new IT jobs annually. You need skill and hustle to obtain these jobs, of course, but the good news is that cybersecurity professionals can look forward to extremely competitive salaries. That's why InfoSec has leveraged 20 years of industry experience Drawing from multiple sources to give you, cyber work listeners, an analysis of the most popular and top paying industry certifications.

You can use it to navigate your way to a good paying cyber security career. 

So to get your free copy of our cyber security salary guide ebook, just click the link in the description below. It's right there near the top, just below me. You can't miss it. click the link in the description and download our free cyber security salary guide ebook.

Your cyber security journey starts here. 

Now let's get the show started 

 

[00:02:06] Chris Sienko: Welcome to this week's episode of the Cyborg podcast. My guests are a cross section of cybersecurity industry thought leaders, and our goal is to help you learn about cybersecurity trends, How those trends affect the work of InfoSec professionals. It leave you with some tips and advice for moving, breaking in or moving up the ladder in the cybersecurity industry. Um, I guess today Anika Gupta brings more than a decade of product and SAS experience with a track record of driving revenue growth, navigating expansions to new markets and overseeing diversity inclusion and belonging initiatives. She joins Rubrik from LiveRamp where she was president and head of product and platforms, leading product development and go to market products.

Operations and strategy. Uh, Anika also sits on the board of directors for, uh, Tenuity. I asked you how to pronounce that and I, I wiped out again. I'm sorry. Uh, hello, Anika. Thank you so much for joining me today and welcome to cyber work.

[00:02:55] Anneka Gupta: Thanks for having me. I'm super excited to be here.

[00:02:58] Chris Sienko: Yeah. So, um, as I sort of suggested in the intro, we're going to be talking, uh, primarily our, our listeners today, we're going to be talking to the, uh, students in the, in the, in the crowd, the young people, the, uh, the cybersecurity professionals of, of tomorrow and tomorrow and tomorrow. So, uh, I want to get our listeners a chance to know you and your origins a little better.

So I know that you have kind of an interesting, uh, origin story with regards to computers and tech. Could you tell me about that?

[00:03:24] Anneka Gupta: Absolutely. So I was born and raised in the Bay Area. I've lived here my entire life. I thought at some point, maybe I would move out of, out of this area. But honestly, um, it's been the center of technology and that's what I've been really drawn to. Growing up, both of my parents were immigrants from India and they both ended up starting their own companies, one in the telecommunications space, one in the embedded software space.

So I like to say that technology, entrepreneurship, all of that runs in my blood and I've always been really drawn to it because I have these amazing role models. Yeah,

business, then certainly the family vocation. So, uh, can, can you tell me about the, the, the process that your parents had in terms of coming to the Bay Area and then starting their own companies like that? What was, what were some of the hardships and what were some of the, the things that they, they learned along the way that they sort of, I imparted to you?

Mm-Hmm.

I mean, they were part of the first generation of Indian tech entrepreneurs to come to the U.S Now it's a very common, uh, It's a very common thing for people to do, but back then when they came in the sixties and seventies, it wasn't, and you know, their approach was, or their story was, they actually came for graduate school to the U.S Because that was the best place to get education at the graduate level in electrical engineering, mechanical engineering, and all other kinds of engineering subjects at that time.

And I think just based on being in the Bay area, working for some. Really large established companies that were driving a lot of innovation. Um, at that point in time, they ended up getting kind of sucked into this, this entrepreneurship track and they both ended up deciding to start their own companies.

So it's a really inspiring story because they had to figure out a lot of stuff on their own. They didn't have the resources that are now available for a lot of entrepreneurs. These are the pre internet days. So it wasn't like

Mm-Hmm.

search for information and they really forged their own path and figured out how to build successful companies.

They both ended up taking their companies public.

Nice.

Um, and it was just a very, um, exciting environment to grow up in. I don't think I fully realized at the time when I was growing up, how lucky I was to be in that kind of environment.

[00:05:45] Chris Sienko: Yeah. or how anomalous that that was, I suppose, for a lot of people, but, um, you mentioned that they sort of were swept up in a wave of sort of entrepreneurship at the time. Was this among other Indian immigrants? Who were, who were they sort of, uh, amongst who are also starting their own companies that kind of got them, uh, sort of lit the fire in that regard?

[00:06:08] Anneka Gupta: Yeah, I mean, there weren't, I think, a lot of Indians in the Bay Area that were picking this entrepreneurship track. There were a couple, but I mean, these were the days when companies like Cisco was starting and they even seen Apple and Microsoft. So it was really the beginning of the computer revolution and technology revolution that would really sweep Silicon Valley and eventually, you know, more of the world.

And that was, The, those were the people that there were kind of amongst and seeing, um, and that was what was being talked about as well. You, you know, read the magazines and, and trade news of the day and so that was the, their cohort of, of people.

[00:06:48] Chris Sienko: Yeah. The energy and excitement of that time must have been just palpable every day.

[00:06:52] Anneka Gupta: Absolutely. And they have so many great stories to share about that.

[00:06:55] Chris Sienko: I bet. Uh, so I want to talk to you about your current positions here because, uh, a lot of our listeners to learn about all the different ways that you can get into cyber security that aren't necessarily, uh, the sort of standard ones. But, um, you know, and I also come from marketing myself, but I know that Uh, in your previous position and your current role with rubric ink, you're described as a chief product officer. Uh, and I know that that's, that's definitely related, but I want to get a sense of like, what is the day to day responsibilities of a position like that? What's your average workday and workweek like when you're doing that kind of thing?

[00:07:30] Anneka Gupta: the things I'd like to say is that there's no average workday for a chief product officer. Uh, your day can change pretty dramatically because like in product, you're really sitting at the intersection of. the technology that's being built, the way it's being positioned in the market, the actual sales of your product, and then all of the ongoing support issues as well that may emerge for your products.

Um, so it's a very exciting place to be because there's a ton of variety in what the day to day looks like and even hour to hour. So some days I'm spending a lot of time with Helping our sales team position our products and sell our products to new customers. Some days I'm dealing with customer support issues and helping calm down and upset customer that may have encountered an issue and really needs to see the path forward.

Some days I'm doing a workshop with engineering or. With marketing around, okay, what do we need to do differently about how we're building our products or the strategy of, uh, of what we're focused on or how we're sequencing things. So everything, like, it's, it's all very dynamic and, and fast changing. And I think that's true no matter what industry you're in.

The thing that I've really enjoyed about both security, as well as my previous industry, marketing technology, is that these are rapidly changing fields where there's a high degree of innovation and a high degree of change. And I think that means that this role ends up being more varied in terms of the kinds of things that you have to do and the kinds of things that you have to have your hands in, because basically nothing is staying the same year to year things are rapidly changing, I

[00:09:07] Chris Sienko: I mean, uh, to, to get all this stuff done, what are the, The sort of largest skill sets that you're using the most often in, in doing this job. Well, it sounds like communication is a big part of it, but what, what are you sort of pulling from in terms of all the things you've learned?

[00:09:22] Anneka Gupta: think the core of what makes. Um, great product managers and great product leaders is really being able to get to the heart of an issue or a problem and understand it deeply. And that could be any kind of problem. That could be the problem that you are trying to solve with your product for your customer, or it could be a problem that's, um, creating, that's, you know, internal that's why is the growth of my business not, uh, not, uh, accelerating or stagnating.

Um, or how do I drive more profitability? There's all kinds of different problems that emerge as you're trying to take products to market and being able to not just take like the surface level understanding, but go multiple layers deep and ask great questions to get to the heart of the issue, um, develop hypotheses that you're constantly testing and refining and updating based on new information, external, internal.

To again, try to get to the heart of the issue, knowing that you'll never understand an issue a hundred percent, but the goal is to always get deeper and deeper into understanding what that issue is, because once you can understand a problem, you can solve it.

[00:10:40] Chris Sienko: Yes. Okay. Yeah. So it sounds like this is a good job to pursue if you're. If you don't want to keep doing the same thing from week to week, you get tired of, of sort of a routine thing. You want the sort of like the dynamism of

[00:10:54] Anneka Gupta: Yep,

[00:10:55] Chris Sienko: from like completely. I mean almost completely different areas of your brain.

It sounds like you're

[00:11:01] Anneka Gupta: exactly.

[00:11:02] Chris Sienko: side to the, Hard tech side to the problem solving side. Now, um, one more question before I move on to the next thing here, like the role of chief product officer is as regards as, as relates to something like a product manager, does that mean you're sort of overseeing like multiple products and multiple product managers?

How does that work on this sort of work chart?

[00:11:22] Anneka Gupta: Oh yeah. So a chief product officer at the bare minimum will manage all of the product managers across the company. So the global product suite, which means that you're really in charge of Of managing the entire portfolio of products, figuring out when you're going to do something totally new to add onto your portfolio, when to sunset things, all of, all of the kind of operations of the product.

[00:11:46] Chris Sienko: Yes.

[00:11:47] Anneka Gupta: Now in some companies, a chief product officer will own design as a function as well. So that's true within rubric. I own design. I own product management. I own all of the monetization, so pricing and packaging as well. And then in some organizations, we're seeing the emergence of chief product and technology officer or just chief product officers that own engineering too.

So it can vary from organization to organization in terms of how they decide to structure it. And I think it's very dependent on the type of business that you're in as a company on whether you need multiple leaders. That are peers for some of these areas or whether you can group things together, um, under a single leader.

[00:12:28] Chris Sienko: Right. Okay. That, that, that's very helpful. Thank you. So I want to jump back to your previous position because, you know, you spent 11 years with, with live ramp moving through a variety of positions from, you know, uh, marketing into president and head of product and platforms. And it seems like if you're somewhere for 11 years, like that's where you're going to see a lot of your sort of transformational, uh, career moments happen, can you talk about some of the things That you sort of were key moments working there that you've brought to uh, your current role.

[00:12:59] Anneka Gupta: Absolutely. So I feel like at LiveRamp, I had this amazing opportunity to. Over that 11 year time horizon, do pretty much every job at the company.

[00:13:09] Chris Sienko: Yeah, right

[00:13:10] Anneka Gupta: and that emerged kind of organically as well as, you know, because I pursued some of those opportunities. Um, and I think there were times where it wasn't very linear in terms of the changes I was making.

So I went from being an engineer to the first product manager. That was like a pretty logical step, given what I was very interested in and moving to be more at the intersection of technology and business versus just building the technology, but then I made a move to marketing and, you know, on paper, someone would say, well, that doesn't seem like super career, career additive to just jump into this other function, you barely become an expert, you haven't become an expert in one year of product management and product management.

Why are you jumping to something else? Is that a big risk? I think like when I look back on that jump and the year I spent running marketing and then also recruiting, um, I, it was so additive to my experience because it made me, first of all, it made me think in a totally different way. Whereas before I thought about the technology first, um, marketing, you have to think about what's the value prop first, what is the message, what's going to resonate and how are you going to get that message to the right people?

And I think it ultimately made me a better product leader having that kind of experience. Um, I would also say that those moments where I start, you know, went to something totally different, even if it was a horizontal move, gave me a deep empathy for other functions and How they operate, what they care about, what their challenges are.

And even though I would never say I'm a marketing expert or a recruiting expert or an expert in a lot of these areas that I had a hand in, it was, again, made, helped me with integrated thinking of understanding, well, when you launch a product, How are you going to take it to market and actually working backwards from what are the goals that you have to then saying, well, what are all the pieces that need to occur?

And what are the things that I own versus what other people own? The funny thing about product management and product leadership is that you have a ton of responsibility to make products successful and the company successful, but you have almost no direct authority because everything Anyone that's actually doing the work, whether it's engineering building or marketing, marketing it, or sales, selling it, those aren't people that report to me, so you have to be able to influence without authority.

And I think this experience is, even though I didn't architect it this way, I just let my curiosity drive my career journey. It really helped me. Understand a very integrated perspective of what all these functions do and how to leverage them and how to bring them along when I'm trying to launch something or bring something to market.

[00:16:01] Chris Sienko: Yeah, yeah, no, I, I imagine, uh, if you just stay on the product side that it would be really easy to, uh, you know, you, you just get very invested in how the thing works and you know, you're, you're basically only communicating with clients you already have. And so there's like, but the idea of like thinking in terms of. would I sell this to or whatever? I suppose that's probably, uh, uh, not something that's intrinsic to that original role, right?

[00:16:26] Anneka Gupta: Absolutely. Especially for product managers like myself that came out of engineering. Um, you don't always think about, well, how, how was, how am I going to sell this? Who am I going to sell this to? And, uh, that's. I think a huge mistake because that's actually one of the most important foundational questions.

You have to ask. I always say that great technology isn't like the best product is not the product that wins. It's. Good enough product, um, with like the right go to market and operational motions around it to get it into the hands of people that actually need it. That's what's going to win. And I think that sometimes is a bit counterintuitive, especially for product managers coming out of an engineering back.

[00:17:08] Chris Sienko: Yeah. To say nothing of just pure engineers who are just literally thinking of like the next line of code, I suppose, and everything, but not thinking about it at all. Um, so yeah, so for our conversation today, uh, you suggested the. about your career journey into STEM or science, technology, engineering, mathematics, uh, as well as your work, uh, in bringing a new generation of diverse professionals into the industry, uh, which is always a, a very passionate subject of mine as well, because, you know, there are just so many positions, needing to be filled.

So many people that, that want to do them a mismatch between what people think they need for skills versus what they're learning versus, uh, what they're told will be. You know, instantly, you know, marketable, as long as you have the passion, as long as you do the work, you know, you'll find the job and then six months later, a year later, they're still, you know, looking for, you know, that first interview or whatever.

So, I mean, there's just a lot of friction at this point in the process. So can you talk about the state of STEM in the U S right now and aspects of the process that you're working to either support, improve, or change?

[00:18:13] Anneka Gupta: Sure. That's a, that's a big question. Um,

[00:18:15] Chris Sienko: Yeah.

[00:18:16] Anneka Gupta: I think. Um, there's so many people that are doing a lot of great work, uh, around how do you get more young people interested in STEM subjects, um, so that they don't, so that, you know, women aren't opting out or just in general, people aren't opting out saying, well, I'm not good at math and in eighth grade when that may not be true, um, they just, you know, need to be, have it presented to them in the right way.

So I think there's a lot of work that's being done there that's super, super important in terms of like getting people interested and getting them to a place where within their education, especially higher education, they're engaging in and learning STEM subjects. Um, I think, you know, what my focus has been is obviously from, because I'm not able to focus on some of those kinds of things full time is from the positions that I'm in, um, in the businesses that I'm operating in, well, what can I really do?

And I think 1 thing that is. Um, is super important is really just like in terms of the teams that I manage, um, what are the ways that I can bring in, um, more diverse perspectives? Because there's tons of research that's been done around more diverse perspectives, um, leads to better decision quality. And I think especially in the area of security.

Where stuff is changing so quickly, of course, having domain expertise is valuable. But if you only try to look for people that have done it before, you're going to lose a perspective of looking at things radically differently and questioning the status quo. It's almost like there's a, um, a luxury and not knowing what has worked and what hasn't worked in the past because it opens your mind to what's possible.

Um, and what could be thought of, like, what could be done if we took a totally different paradigm. I only came to the cyber security industry 3 years ago. So in some ways, I'm still a newcomer too. And I found a lot of I've been able to add a lot of value in the way I think about things and what that has led me to do is really champion.

Um, my team to, to bring in people with different kinds of experiences. And that has inevitably led to a much more diverse team. So just one metric, and this is only one way to look at diversity. When I have my product management team, when I joined rubric was only, there's only one other woman on the team,

[00:20:34] Chris Sienko: Mm

[00:20:35] Anneka Gupta: in core product management, not in some of the other functions that I manage.

And now our team is something like 30 percent women. And it's not because I made any sort of concerted effort to hire women onto the team. I just went and said, let's open our pool of who we're looking at the kinds of backgrounds that we're looking for to a much broader set of people. And let's really focus less around Domain experience and really like, what can this person bring to the table?

And what is really needed for this role that we're hiring for? And I think it's an easy shortcut to say, well, I'm just going to hire people that have done this before

[00:21:10] Chris Sienko: Yep.

[00:21:11] Anneka Gupta: that's easiest. And that's the easiest, like, I don't really have to interview them because I'm like, okay, this is, this is a good enough role.

And it takes more effort to say, well, I'm going to look for someone with a different type of background, but that could really bring in something. Skills or experiences, um, or working on different types of technologies that might really change the game. And, and so I think thinking of like my hiring, I'm like, I'm looking for change agents.

I'm not looking for people with this particular profile has, has inevitably led me to a place where three years later, we have a much more diverse team in terms of the backgrounds of companies that people have worked at gender diversity and much more,

[00:21:51] Chris Sienko: Yeah. And I think it's worth remembering that security is not a continuance based job. You're not, you're not trying to do the same thing, same amount of quality all the time. And so hiring someone who is doing what the previous person did in that position several years ago, you're already. Sort of behind the, behind the times in that regard.

So again, does it sort of square up, you know, what we hear from guests versus what we hear in the comment sections and so forth. Um, tell me about the types of things that you look for on a resume. Oh, I guess let's start by talking about where you opened up your resume. the elective pool too. And then also what, you know, you said there's opportunities to hire people from areas of experience.

What were you looking for in those resumes that indicated this person might not necessarily have domain experience, but they have a certain something that I think will really contribute to the team.

[00:22:48] Anneka Gupta: it's a great question. So in a multiple of the roles. That I've hired that have been direct reports to me. What I've really looked for is leaders that have demonstrated going through the process of building and launching products and iterating on it. Not necessarily always to a point of getting to a successful outcome.

But learning in the process and, and getting better. So I think that has been one thing. And some of that you can look at by like, how long have people been in positions for? If you, if I see a resume that has, you know, for the last four jobs, they've been in that role less than two years in product management, two years goes by like that.

[00:23:31] Chris Sienko: Yeah.

[00:23:32] Anneka Gupta: you don't really get to see the full cycle of launching something and iterating on it and relaunching it again and like finding that success. If you've just done a series of shorter stints and I think in a lot of roles two years, it's like, wow, That's the average like that's great But I don't think like in product management, like I think two years is like really when you start hitting your stride So it's fine to have a few short things short stints on your resume because everyone Has that happened where they may make a mistake or a company goes out of business or whatever extenuating circumstances happen, but having like four or five of those in a row, it's just hard for me to then get signal around whether this person is really able to drive success over the long.

So that's one thing that I would, I look for. And then I think there's a lot that comes out. That's not, you just can't get from a resume and you can only get from a conversation. And those conversations like what I tend to do is first of all, it's like, try to pick questions that are not things that everyone asks, because those are the things that people prepare answers for ask questions that are more nuanced, that are more, um, going to give you some real insight into who this person is as a person.

And the things I really want to tease out is. But where have they really shown that they can be a change agent? How do they handle adversity? How do they handle, like, giving and receiving feedback? Like, are they self aware? Are they able to, um, are they able to give feedback effectively and coach people?

Um, how do they deal with really hard situations and get them to be vulnerable? And if I can't get someone to be vulnerable, At the end of the day, it's like my goal in hiring is not to eliminate all of the, um, the like false negatives. So it's okay to pass on someone that's good. If I can't get enough signal, that's fine.

At the end of the day, I just need to hire someone That is that I, that is going to excel at this role. And there's probably hundreds of people out there that could could be that person. And even if I ended up, like, having 5 of them that I interviewed, and I just qualified 4 of them, that's okay. It's not interviewing is not an exact science, but finding someone that you have high confidence and, um, and that can really, like, showcases that through the interview process.

Like, that's the most important important thing.

[00:25:53] Chris Sienko: Yeah, no, that's, that's amazing advice. Now. I love that now. Um, I guess to get a, for a person to get their foot in the door, they still need, like you said, the, the resume doesn't really tell the story apart from some of the red flags. Like, if they've, you know, jumped every 6 months for 5 years or whatever, but, uh, are there, are there. You know, if that's a red flag, are there green flags that candidates can put into their resume that indicate things on sort of a quieter level, whether it's interests or, you know, writing that they've done or, or other sort of other ways to sort of it, you know, because there's, there's still, like you said, it's easy to

[00:26:33] Anneka Gupta: Yeah,

[00:26:34] Chris Sienko: even like highly qualified people.

[00:26:35] Anneka Gupta: great.

[00:26:36] Chris Sienko: someone who's maybe more interesting, but less qualified. Sort of convey that in like a resume or a cover letter or some

[00:26:44] Anneka Gupta: Yeah, I think so. I'll answer this in two different ways on the resume itself. I think that it's really important to show results. So sometimes what I see, and I give, I do coach and mentor a lot of different people at different levels, not just within my company,

[00:26:59] Chris Sienko: Okay.

[00:27:00] Anneka Gupta: I look at a lot of resumes and give people feedback.

And one of the things I see is people are just listing, these are the things that I did. So 

[00:27:06] Chris Sienko: in a role, they have their bullets and they're like, I launched this, I did this, but they don't actually show what were the results that they drove. 

[00:27:14] Anneka Gupta: And so I encourage them to take every bullet point and like, even if you can't put a measure, a number on it.

Somehow convey what is the result that this that you drove?

[00:27:25] Chris Sienko: Yeah.

[00:27:25] Anneka Gupta: Um, so that it's clear, like, Hey, I'm not just doing these tasks. I'm actually connecting this to some sort of positive outcome, um, for the business. So I think that's that's 1 thing that is probably the number 1 thing I coach people on on their resumes.

However, I think like if you're really trying to get a job, the market is tough right now, markets go up and down. There's been a lot of layoffs over the past couple of years. People can afford to go for like hire someone that's slightly more experienced than what they would have been able to get in 2021 because there's just a ton of people out looking for jobs and it's an employer's market.

I think there's something to be said, a lot to be said. For showing hustle and showing that you're passionate in the process of interviewing for a role. So that may mean messaging the like product leader on LinkedIn to try to get them to like, pay attention to your resume with like something that's a short message of like, why.

You're interested in this role. Why you might be a great fit for it. Like four sentences. I'm not going to read a whole bunch of stuff, but that can be very effective. Um, you won't get a hundred percent hit rate. You may only get 5%, but like, if you show that if you do it and you do it a hundred times, well, that may open up five opportunities for you that you wouldn't otherwise have, um, you know, just following up and in the interview, being genuine about why you're excited about the role.

I think sometimes people are afraid of as candidates overplaying their hand.

[00:28:50] Chris Sienko: Mm.

[00:28:51] Anneka Gupta: I don't want to show that I'm too interested. I don't want to tell them, but telling someone that you're really interested in this role and why, and showing that you genuinely care. It goes a long way because like, I want to hire, most people want to hire people that like really want to do a great job.

And if you're showing that in the process, Through your body language and through explicitly saying that it really, really helps. And then following up and all those things that are just good hygiene. But I think an underrated trade, especially for people that don't have a lot of experience is just hustle.

Just send out the emails.

[00:29:23] Chris Sienko: Mm

[00:29:24] Anneka Gupta: Reach out to everyone, you know, try to get connections and ends because the reality is, is like, you're not going to likely get a job from just applying through the website, you have to find an end and you have to hustle your way to get there. And it's, uh, it's hard and it takes a lot of time.

[00:29:39] Chris Sienko: Mm

[00:29:40] Anneka Gupta: But it is worth

[00:29:42] Chris Sienko: Yeah. It's, yeah, like you said, it's literally the only way, as far as I

[00:29:45] Anneka Gupta: it, correct?

[00:29:45] Chris Sienko: um, especially these days. But, um, so, uh, Going back to people who are still in school, what are your thoughts for college students in STEM who are on their way to jobs in cybersecurity and tech? Are there certain pitfalls they should be avoiding now or hidden opportunities they should be seeking out?

What's the landscape look like for people who are still in the learning stage?

[00:30:05] Anneka Gupta: I think if you're still in the learning stage, just getting, you know, using the opportunity, you're in school, you have access to a bunch of resources to take a variety of different types of classes. And that can be on the technical side. So maybe you're, um, you take an AI class or, um, maybe if your school offers something in cybersecurity, you take a class there.

I definitely encourage people, even if you don't have a cybersecurity degree. degree to go take like a computer science class. Just so you understand how things work. You don't have to do a major in computer science, but just go take these classes to give yourself the exposure and to also challenge yourself to learn something that's totally new to you.

I think the reality is, is that school only prepares you so well for working so much of what you do working is learning on the job and no class is going to prepare you for it. I get a lot of questions. I'm like, what classes can I take to be a great product manager? I'm like, honestly, I wish there was more, but you kind of have to learn on the job.

And I think that's true for so many things, including just. You know, InfoSec teams, like most people, if you ask them what they did, they learned on the job. They didn't like read a book. They got thrown into a situation and they figured it out. Um, and so the biggest thing I think for students is like, learn how to learn.

If you learn how to learn, then you can be confident that whatever situation you're put in. You will figure it out. Um, and that is like, honestly, and that will also stay with you for your career as AI disrupts the jobs market, which it will in the next 10 to 20 years. Um, what, how do you retrain yourself?

It's like, you've got to bet on yourself. And if you want to bet on yourself, you have to learn how to learn.

[00:31:45] Chris Sienko: Yeah, yeah, absolutely. I, I, we talk about all the time on here about the importance of doing things just for the sake of doing them and then being able to document them, you know, like if you set up your own home, you know, your own home, uh, you know, network and then secure it really well, and then document that, like that goes a lot longer than just learning that empirically out of a book and getting A's on the tests.

[00:32:08] Anneka Gupta: Absolutely. I think that's a great example.

[00:32:11] Chris Sienko: Yeah. Yeah. So, uh, we did talk a little bit about this. You said that you, in the process of hiring you. Managed to foster a more inclusive environment in tech. Can you talk about some critical actions that need to be taken right now to sort of create and support a diverse and inclusive cybersecurity culture on a larger scale?

Like, what do you, what, where are the sort of friction points that need to be cleared for, for this to become hopefully a little more systemic?

[00:32:35] Anneka Gupta: Yeah, I mean, I think one is making sure that again at the at whether it's a college level or maybe even earlier on that, um, women and other underrepresented minorities within security are recognizing. What this career path looks like,

[00:32:54] Chris Sienko: Yes.

[00:32:55] Anneka Gupta: right? Because there's so much of you don't even know What are the various career options even sometimes entering into college?

you're like you have like a few different career paths based on people that you've met or known your parents your Um your neighbors, etc. But that's a very limited scope of like what's actually out there So what can we do to help evangelize? I think things like what you're doing with this podcast are great is evangelize what these jobs are so people can even be aware of them and think of them and consider them as they're planning out their career.

So I think that's 1 element.

[00:33:29] Chris Sienko: Mm hmm.

[00:33:30] Anneka Gupta: And then I think a 2nd element is really on the employers. Everyone talks about how there's such a shortage of cyber security talent. But then are you willing as an employer to put a training program in place to hire people that don't have the experience and get them up to speed?

And that's actually can be a very low cost way to fill your team and, and, um, and make up for the fact that like you, it's like the, the very experienced talent is under huge demand. Commanding huge like salaries and premiums because of their experience because of the shortage. So this is a way where it's like, if you invest and you think about it differently, you can actually build the talent and that will pay dividends because then that will create, um, the ability for more people to come into the space without having experience.

Um, that I think is the thing that employers can really do to make a big difference and big debt in this space.

[00:34:29] Chris Sienko: I think it also gives you a chance. I mean, based on what you're saying, it sounds like it gives you a chance to, um, have more of a hand in terms of creating your department's culture in that regard, in that you're not depending on, um, Uh, you know, a hotshot superstar who commands a big salary to be, uh, you know, you're, you're sort of, uh, a number one or whatever like that.

So, yeah, I, you know, I think that's, that's all sort of part of team building, but also sort of team fostering in that

[00:34:58] Anneka Gupta: Absolutely.

[00:34:59] Chris Sienko: Now, um, you mentioned something before and I was going to come to it and then it, it, it slipped me, but you talked about, uh, like how, how women and other underrepresented groups, uh, maybe will feel or will get kind of, you know, froze out of STEM early on.

Like I I'm not good at math, but it turns out it's maybe just a bad teacher. Uh, science doesn't make any sense to me, but you had rock. Can you give me some examples, uh, advice for people like that? Who think I would love to do this. I have these shortcomings. But, and, and, and my teacher is not great, whatever, you know, like what do you do to sort of, um, make up the, the shortfall where, where, where, where can you find the passion if the passion can't be found in, in the sort of traditional, uh, halls of learning, I guess.

[00:35:48] Anneka Gupta: Well, I think if you're a student and you're like, I want to learn this. I'm not, it's not resonating to me. Whatever is happening in school isn't resonating to me. The great thing is, is that there's tons of resources on the internet. There's tons of YouTube videos. There's tons of things, ways to learn that are different and people have put out great content and the reality is, is different things are going to resonate with different people.

I think part of it sometimes is finding like, what is that connection point to something that you're passionate about that can help you learn? Um, or maybe you're a person that's like you were mentioning learn by doing. Um, and just trying to figure out and problem solve is actually a more interesting way for you to figure out how to learn algebra than trying to, you know, going through like the road way of learning the steps of, of how you solve for a variable, right?

That, like, that may be different. I think there, there's some point of, like, if you can say for yourself, Hey, I feel like I want to have this passion, but I don't have it. Trying to find something that you have an interest in and then connecting it with that or help having a parent help you make that connection if your teacher doesn't or another mentor help you make that connection.

Um, that's really valuable. And then the kind of world is your oyster on the internet. There's just, there's, there's a lot of bad content out there, but there's also just a lot of phenomenal educational content. Um, and I think like, so I think that's one of it. And then the second piece is like, sometimes I think people opt out of math because they're like, wow.

Calculus isn't useful for me, like I'm not going to use this in my job. Okay, yes, I don't like to use calculus in my day to day job. I'm not solving integrals or doing anything like that. But I've come to realize more and more how much having a strong sense of numbers and just being able to easily have a sense of numbers and have it easily be able to say, well, this number is about like, if I look at these two numbers, it's approximately like 30 percent growth.

You know, 1 number over the other, but that comes, I use that 40 times a day because I'm looking at numbers all the time and I have to make sense of them and I have to be able to pull out the signal from the noise and being able to do that quick, like, not perfect mental math. Like, I don't need to multiply, like, 14 times 167, um, and like that.

Right. But being able to do, like, quick understanding of. Of a number and like what and how, what it feels like and how, um, you know, how numbers compared to each other is so, so valuable and it makes me more effective. And I think that's the thing where sometimes that story gets lost in math education, because people are just like, so focused around.

Well, do I really need this? Like to know how to do this thing, but all of these skills, like solving integral actually like give you a better sense of numbers and that practice and just keeping doing it and going through these classes, super important because you'll get that sense that it will pay dividends later on.

[00:38:42] Chris Sienko: So what you're saying is that you're not on a, on a daily basis, um, calculating the, uh, the, the volume of a conical cylinder.

[00:38:50] Anneka Gupta: I'm sure for some jobs you do need to, not for my job. Absolutely.

[00:38:57] Chris Sienko: the wall that I, head first into in college and that's why I'm not a chemical engineer and I'm in marketing, but um, But yeah, no point well taken.

I mean obviously everything up to that was was very interesting and And I think you're right that it's it's more about learning the idea of numbers and I guess just in a larger sense Uh, you know, if you're in any kind of high touch sort of thought oriented job, like, I don't know that college is any kind of vocational training at all.

Like it's really, it's the most useful computer science, you know, science labs, you're still just learning how to learn. You're not doing anything like you said, you know, until you start actually doing it, you're not learning, you know, you're not doing it, I guess that's a little reductive, but, um, but I think that that's worth noting.

Like, and I think that's. A friction point that we see with young, you know, younger students is, well, I got my degree and four certs and no one's knocking on my door. You know, it's like, well, you still haven't done anything, you know, you've learned a lot, you learn how to learn it, uh, now put it to work, I guess.

But, um, so I want to move to another area of your, um, passionate area for you, which is, is mentoring. Um, can you talk about the work that you do mentoring and. Like tell us about some of your mentees or even your mentors and what you learn or assist them with on a on a regular basis

[00:40:17] Anneka Gupta: Um, I mean, I've benefited so much from like so many different types of mentors throughout my career, whether it was my direct boss. Learning from my parents experience reaching out to other professionals where I was trying to problem solve things. So I, I feel a lot of gratitude for the various people that have been mentors for me, and I've always found a lot of joy in helping other people and mentoring them.

And, uh, the thing that I feel very fortunate about is. There are many different ways I've been able to manifest this. Um, desire to help people in the, what I call the extracurriculars that I do outside of my job. So I, um, one is I, I teach a product management course at Stanford's graduate school of business.

Um, so I've been a lecturer there for the past couple of years and I co developed a class with a professor around product management. Uh, so exciting and interesting. And it gives me this opportunity to engage with students both in the class, but then many of them, even afterwards, as they're navigating.

How to find a job after business school, or many of them are international students. So how do I kind of, well, I had a great successful career in another country. How do I launch that another successful career in Silicon Valley when I don't have the connections or, you know, my experience is difficult to translate into this environment.

So things like that. So I've had that opportunity, which has been phenomenal. The second thing is I'm part of this product community. It's called the skip community. It's a relatively new community a few years old, and that has a bunch of other product leaders that are CPOs at my level, but then also the next layer down, um, of.

And I, through that community, I get to engage a lot with different types of people and help them navigate really tricky situations. Sometimes it's how do I navigate? Like, I've been a VP of product reporting to a CPO. I want to get a job as a CPO. How do I go do that? And like, what are the approaches that I can take?

The process there, or it might be a question of, Hey, I have this like really kind of complex situation around my compensation. And I have questions about, am I being paid fairly? Or maybe I feel like this, but I want to have a conversation around compensation. And especially for women, I know as a woman, I have a challenge with this.

Myself is like having conversations around compensation are difficult. Um, and being able to help people navigate that or saying, Hey, I have a really challenging situation with a, with engineering, how have you managed these kinds of situations? So there's a lot of things like that, that I get to help people on either on an ongoing basis or just one off through the community.

And then the last piece is just. Through the people that I've worked with before, I try to keep in touch with them and, and help them in whatever way I can, whether again, that's on a job search or in, in, uh, in finding success in their, in the jobs that they're taking on. Um, and so I make just myself very available to people, um, that I know to have those kinds of conversations.

And honestly, like I get out of it as much as the other person, even though the other person doesn't realize that. And I think That's something to recognize that if you're someone looking for a mentor, there are people out there that want to help and they get genuine joy out of doing it. So don't feel like you're imposing on them by asking them to help you or work through a problem together.

[00:43:40] Chris Sienko: Yeah, we've we've heard from so many c suite people who say It can be very lonely up there and it can be very isolated and to hear what? People are struggling with at the very first step of the ladder can be incredibly insightful and stuff. So you're absolutely right. I don't, don't feel like you're, uh, you know, a burden, uh, now at the same time for college graduates and people who haven't been long in the industry. Um, I, I know that when I was coming out of college, we were given this open ended directive to start networking and look for a mentor, but. Like most crucial communication skills, we're, uh, we're, we're told that are important. We don't really have any way to learn this. So can you suggest some ways or places where students should start networking or how to actually do the work of networking?

Especially if you feel like you said, a little shy or a little impostery or what have you.

[00:44:29] Anneka Gupta: So I would say that first, like, don't enter the situation by saying, I'm looking for a mentor, even if that's ultimately your goal, mentor, like the best mentor relationships will naturally emerge. From a true connection, um, and so I think like if you have a, like, I've always approached things of, Hey, I have this problem that I'm trying to solve, right?

Maybe it's a problem in my business that I want to get other people's perspective on, or it's a problem around my own career of like, I don't know which direction I should go in. I'm trying to figure out, do I go take option A or option B or start pursuing these? And like, choose a problem and then try to find people around you that can workshop the problem with you, because I think truly on working on stuff together, you understand whether you're going to have, you're going to get a lot of value out of the relationship and the other person can feel out, hey, is this something that That's worth pursuing long term.

And if you feel that connection, when you talk, start talking to someone about this problem that you're working on, then it's worth pursuing. But don't expect that every person you're going to talk to, you're going to have a connection with. And, and that's okay too, right? It may only be some small percentage.

I find this like figuring out a problem to make it a little less scary because when you talk about networking, often it's like, well, so I just have to reach out to strangers and like, start small talking with them and make

[00:45:49] Chris Sienko: Right.

[00:45:50] Anneka Gupta: or I have to go to this huge event where I don't know anyone and try to make that and that's really scary, but I think one on one connections.

Is a really like positive way to start and focusing on a problem is a really good way to like, ask for a conversation and be like, Hey, reach out to someone that's maybe a friend of a friend and basically say, Hey, I have this challenge I'm working through. I'm trying to think about my career. I'm trying to decide, you know, do I take.

A path, um, as you know, an engineer, or do I focus or do I go into like, um, into an infosec team and like, go more of like a sock analyst rep, um, I want to workshop like what these different paths look like. I want to understand, like, how maybe you approach the situation or how I should think about it. And so coming up with, like, your problem and then asking someone for help, it becomes very.

[00:46:39] Chris Sienko: Easy for someone to say, yeah, okay, I can help you with this. Like, let's have coffee and let's talk about it. And it also becomes less scary for you because you're not just putting something out there and have nothing. You don't know what you're going to talk about with this person.

Yeah. Yeah. I mean, when you think about, Going up to anyone, whether you're, you know, wanting to talk socially or whatever, just going up and saying hi. And then like, I'm here, you know, like it's never going to work. Like you, you, you, you got to have a game plan.

[00:47:02] Anneka Gupta: Yeah,

[00:47:03] Chris Sienko: And especially, like you said, if you're coming in to it with, is an engaging problem that we can go back and forth with rather than, can you give me something or, you know, can I learn at your feet or what that, you know, I think people are more. You know, and I think it's, it's real easy to get into that mold too, where you feel like, well, I'm at, I'm at the bottom of the ladder, so I have to kind of, you know, kind of bow down or whatever, or, you know, uh, show deference or whatever. But if you're approaching them with like, Hey, here's this thing we need to, to work with. Um, yeah, they're going to be like, Oh, great. You know, this is a problem solving industry. People like to solve problems.

[00:47:37] Anneka Gupta: exactly.

[00:47:38] Chris Sienko: they're there, it's going to go ding, ding. They're going to get excited. Um, so this has been great, uh, conversation. But before we go, Annika, I want to ask you. Boy, you've had so many of them, but what's your, what's the best piece of career advice you've ever received?

You know, cause you said you have, you have these parents and you've had amazing mentors and stuff, but like what, what's something you could leave us with?

[00:47:58] Anneka Gupta: Nothing takes the place of Working really hard and excelling in the job you're in. I think it's very easy to say, well, like, I'm trying to focus on getting this promotion or doing this thing and people like, what do I need to do? Like, just crush it at the job that you have that advice was given to me and.

And I've really taken it to heart. I'm like, I work really hard. I'm going to do really well at the things that I'm doing instead of focusing on what's the next thing, what's the next thing, what's the next thing, because those opportunities will emerge or I'll get the right to ask those once I've like really done an amazing job at the job that I've been given.

[00:48:35] Chris Sienko: Nice. Awesome. Uh, so as we wrap up, we were talking about, um, uh, you know, um, Well, I've read before, but tell us all about Rubrik and the products or services that you've provided to your, your customers.

[00:48:46] Anneka Gupta: Absolutely. Uh, so Rubrik is a cyber security company. We focus on cyber resilience. So helping organizations bounce back after they've been hit with a cyber attack. with the minimum amount of business downtime possible. This is an incredibly important issue because so much has been invested in trying to keep attackers out of systems.

But we know that even as those investments have been going up, the number of attacks and the impact of these attacks have been going up. And an organization's ability to bounce back is as important, if not even more important than just prevention alone. And that's, uh, that's what Rubrik really focus on, focuses on.

We're a great group of people, people working all over the world, um, working with some of the world's largest organizations across healthcare, government, financial services, education. Um, and it's super fulfilling because we're really making a difference in these organizations ability to respond after an attack and make sure that they don't end up, um, having to shut down services to their, to their customers or to citizens.

[00:49:52] Chris Sienko: Fantastic. Well, one last question for all the marbles here. If our listeners want to learn more about you, Anika where can they look for you online?

[00:49:58] Anneka Gupta: Absolutely. Um, you can find me on LinkedIn. Um, so please connect with me and, uh, yeah, rubric. You can come to our website, rubric. com. We're hiring across a ton of different functions. So go to rubric. com slash careers. If you're interested in jobs at rubric, we're about to start our university hiring, um, over the course of the next month.

So if you're in school, please look for those roles.

[00:50:19] Chris Sienko: Beautiful. Thank you so much for your inspirational assistance today, Anika. This was a great conversation. I enjoyed it.

[00:50:23] Anneka Gupta: Yeah, I really enjoyed it. Thank you for having me.

[00:50:25] Chris Sienko: Uh, and thank you all to everyone who watches, listens, and writes into the podcast with feedback. If you have any topics you'd like us to cover, or guests you'd like to see on the show, you can always drop them in the comments below, and we will do our best to get to them. Before we go, don't forget InfoSecInstitute. com slash free is the place to go for a whole bunch of free and exclusive stuff for cyber work listeners. Learn more about our Cyber Security Awareness Training Series Work Bytes, a smartly scripted and hilariously acted set of videos, in which a very strange office staffed by a pirate, a zombie, an alien, a fairy princess, a vampire, and others Navigate their way through age old struggles of yore, whether it's not clicking on the treasure map that someone just emailed you, making sure your nocturnal vampiric accounting work at the hotel is VPN secured, or realizing that even if you have a face as recognizable as their office's terrifying IT guy, Boneslicer, we still can't buzz you in without your key card. Anyway, go to the site, check out the trailer. Uh, also, come over to infosecantstoop. com slash free to get your. Free cybersecurity talent development ebook. You'll find our in depth training plans and strategies for the 12 most common security roles, including SOC analyst, penetration tester, cloud security engineer, information risk analyst, privacy manager, secure coder, ICS professional, and more. One more time, infosecinstitute. com slash free, and yes, the link is in the description below. One last time, thank you so much to Anika Gupta and Rubrik, and thank you all for watching and listening. This is Chris Senko, signing off. Until next time, keep learning, keep developing, and don't forget to have a little fun while you're doing it. Bye for now.