CISO insiders

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Aug 2024

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CISOs insiders is open conversations I’m having with leading CISOs in the industry. We’ll be talking about what makes them ticks, their biggest accomplishments and flagrant failures, their favorite drinks and what it is they like in vendors as well as dislike in vendors. We’ll try to tap into the mind of the person behind the role and hopefully have some fun while doing so. Join us for a light talk.

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August 13, 202446 min

CISO Insiders with Ray Espinoza | CISO at Inspectiv | Episode 85

🧠 In this episode of CISO Insiders, we welcome Ray Espinoza, the CISO at Inspectiv. Ray Espinoza discusses in detail key skills as a leader in the cybersecurity industry. Ray also answers some of the more hard-pressing questions about being a CISO and a leader in the organization while also striking a balance between life and work.👇🏻 This special episode will tackle the following topics:Guiding and inspiring newcomers and aspiring professionals in their journey toward a career in cybersecurity.Essential insights on how to be an effective leader in the world of cybersecurity.Vital learning experiences and resources to support those pursuing a career in cybersecurity.Highlights:🔥 “I wish I would have learned much earlier what power it could bring to enable somebody else to find success. When I think back to the constant that has helped success in the industry is genuinely investing in the people and not expecting anything in return.”🔥 “Continue to find a baseline and start to learn. I find myself as a life-long learner and I’m constantly asking questions and meeting new people. Lean into things like LinkedIn and your network. Find folks in the industry: others who are cybersecurity and technology leaders that are willing to provide guidance.”🔥 “On-the-job training, building relationships and genuinely supporting others helped open up most doors in my career. Continuing to learn and the relationships have opened up more opportunities in this industry.”⏱️Timestamps:00:36 Guest Introduction and Professional Journey03:15 Icebreaker questions04:32 Is there one thing you wish you had known before starting your career?07:24 Biggest failure and key learnings11:45 What is the biggest accomplishment in your career?14:28 Advice to younger listeners and anyone who wants to pursue a career in cybersecurity17:34 What were the best resources that have helped you through your career?21:05 What is one myth about your industry that you want to debunk?23:15 What are the most important skills CISOs should have?26:14 What are the main security concerns of CISOs these days?30:15 How will the CISO role evolve 5 to 10 years from now?37:28 What would be the best strategy for a vendor to connect with you?42:23 Are there any influencers in the industry that you look up to that you would like to mention?44:50 What’s the best way to connect with you online?45:36 Final question - If money was not an issue, what would you do with your life?

July 2, 202439 min

CISO Insiders with Gary Hayslip | CISO at Software Investment Advisers | Episode 84

💫 In this episode of CISO Insiders, we welcome Gary Hayslip, the CISO at Software Investment Advisers. Gary Hayslip discusses in detail key insights and cultural shifts in the cybersecurity industry. Gary also delves into the power dynamics between the CISO and other roles within the organization while striking a balance between managing risks and expectations.👇🏼 Topics:🔎 Giving advice and setting expectations to newcomers and individuals who want to pursue a career in the cybersecurity industry.🔎 Key insights and major cultural shifts within the realm of cybersecurity.🔎 Critical learning experiences and resources that can help individuals who are pursuing a career in cybersecurity.Highlights:⭐ “I think risk and cybersecurity roles will become closer together. I can see privacy merging more into what CISOs are managing, and I can also see how CISO roles will also start aligning more on legal matters.”⭐ “AI is already being built into tools. Where I work, we already have a policy in place, we are training our staff, and we are building security GPTs. We are now using cybersecurity tools with AI to monitor AI.”⭐ “You’re going to have a lot of patience, especially in the cybersecurity industry. You’re going to need tenacity because you’re going to get knocked down a couple of times. But you can keep on trying until you get in.”⏱️Timestamps:00:36 Guest Introduction and Professional Journey01:55 Icebreaker questions02:45 Is there one thing you wish you had known before starting your career?04:13 Biggest failure and key learnings07:08 What is the biggest accomplishment in your career?07:46 Advice to younger listeners and anyone who wants to pursue a career in cybersecurity11:40 Do you think it would be harder for an analyst role to transition toward a GRC role?13:12 What were the best resources that have helped you through your career?16:07 What is one myth about your industry that you want to debunk?19:44 What are the main security concerns of CISOs these days?21:33 How will the CISO role evolve 5 to 10 years from now?23:49 What will we see in the cybersecurity world next?28:31 What would be the best strategy for a vendor to connect with you?30:12 What is it that you are looking for in a vendor?32:03 Are there any influencers in the industry that you look up to that you would like to mention?33:16 What’s the best way to connect with you online?33:27 Final question, closing comments, and summarizing notes - If money was not an issue, what would you do with your life?📢 Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions #cybersecurityjobmarket #jobmarket #recruitment #specialepisode

June 17, 202440 min

CISO Insiders with Chad Hicks | CISO at MercuryGate International | Episode 83

🧠 In this episode of CISO Insiders, we welcome Chad Hicks, the CISO at MercuryGate International. Chad Hicks tackles some of the trending issues and challenges in the cybersecurity industry while giving crucial advice to newcomers in the industry. Chad Hicks also discusses in detail the role of the CISO in an organization and the evolution of the industry in the past 15 years.👇🏼 This special episode will tackle the following topics:Giving advice and setting expectations to newcomers and individuals who want to pursue a career in the cybersecurity industry.Key insights and major cultural shifts within the realm of cybersecurity.Dispelling myths revolving around cybersecurity.Tackling pressing issues in the world of governance, response, and compliance.Highlights:🔥 ”It’s amazing how quickly you can collaboratively resolve things if you treat cybersecurity as a team sport.”🔥 “The majority of threats that we see are pretty defined methods. We have enough tools to detect threat vectors. We don’t need more tools and technologies; we need more people and time.”🔥 “You can’t fake your way into cybersecurity; you have to put in the work. Since cybersecurity touches every aspect of the business, you have to be well-rounded.”⏱️ Timestamps:00:36 Guest Introduction and Professional Journey01:32 Icebreaker questions03:13 Is there one thing you wish you had known before starting your career?04:15 Biggest failure and key learnings05:36 Biggest accomplishments and achievements06:53 How did you become a CISO through your professional journey?09:53 What is your advice to newcomers and anyone wanting to pursue a cybersecurity career?11:21 What are your views on the CISO role in the IT organization?13:46 What were the best resources that have helped you through your career?15:59 What is one myth about your industry that you want to debunk?18:49 What are the main concerns that CISOs have right now?20:45 Are there any specific areas CISOs should focus on?22:29 What are the most crucial skills a CISO should have?23:50 How did the CISO role change in the past 15 - 20 years?25:19 Will the CISO role grow bigger in the next few years?27:47 What do you think we’ll see in the cybersecurity industry next?30:47 What would you define as “innovation” in this industry?33:25 What’s the best way for vendors to reach out to you?35:45 Are there any individuals in the industry that you look up to?37:40 What’s the best way to reach out to you?38:48 Final question and closing comments - If money was not an issue, what would you do with your life?📢 Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions #cybersecurityjobmarket #jobmarket #recruitment #specialepisode

June 4, 202449 min

CISO Insiders with Roee Besser | Information Security and Cyber Risk Manager at CYYDER | Episode 82

🧠 In this episode of CISO Insiders, we welcome Roee Besser, the information security and cyber risk manager at CYYDER. Roee Besser discusses in detail key insights about the cybersecurity industry while giving useful advice and setting expectations for newcomers and individuals who want to pursue a career in the cybersecurity industry.👇🏼 This special episode will tackle the following topics:⭐ Giving career advice to newcomers and individuals who want to pursue a career in the cybersecurity industry.⭐ Key resources that have helped Roee through his career in information security.⭐ The power dynamics between the vCISO role and other C-level roles in small and large enterprises.Highlights:🔎 “Looking for good mentors that will guide and escort me has helped me through my career. I’m not good at sales — this is something that I have to admit. But still, I found the right success partners that would push me to the right customers. This pushes me towards interesting positions.”🔎 “Whenever I go to surveys of companies that I’m responsible for, I always tell them: embrace the auditor. Whatever the auditor finds, you’ll still have the chance and the time to fix it.”🔎 “I could be a CISO for one company and do everything in one place. But, I’m taking bits and bites from different industries while looking from a high-level perspective. That’s the beauty of being a vCISO.”⏱️Timestamps:00:36 Guest Introduction and Professional Journey03:49 Icebreaker questions06:39 Is there one thing you wish you had known before starting your career?10:42 Biggest failure and key learnings16:34 What do you think you would have done differently looking back at your career?19:50 What were the best resources that have helped you through your career?28:32 What’s the best strategy that can help build a professional relationship with other vendors?29:47 What is one myth about your industry that you want to debunk?34:57 What is the difference between your role and the role of a full-time CISO?37:28 What is your biggest challenge when you start working with a new customer?41:05 Who would you say your ideal customer is?43:25 What are qualities that you don’t like in a customer?46:31 Final question and closing comments - If money was not an issue, what would you do with your life?📢 Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions #cybersecurityjobmarket #jobmarket #recruitment #specialepisode

May 14, 202455 min

CISO Insiders with Dennis Tomlin | Chief Information Security Officer at Multnomah County | Episode 81

🧠 In this episode of CISO Insiders, we welcome Dennis Tomlin, Chief Information Security Officer at Multnomah County. Dennis Tomlin, discusses in detail key challenges while sharing key security strategies on his career in cybersecurity for 20 years.This special episode will tackle the following topics:⭐ Turning a culture of “no” to a culture of “yes” while maintaining information security.⭐ The importance of finding a balance between confidentiality, information, and availability.⭐ Key areas of the CISO role that have changed in the past 15 years.The ramifications of malicious software in cybersecurity over the years.🔎 Some highlights:👉🏻 ”Technology is easy compared to people. Learning to listen is the key to success. The ability to listen to what the customer is saying and translating them into requirements can maximize results.”👉🏻 “It’s easy for people to say “no” when people don’t understand the objective. But thinking “yes” helps the business find a way to achieve their objectives while still maintaining the security of the data that makes our lives comfortable.”👉🏻 “What helps a CISO to have a long successful career is to translate requirements into tools that can have minimum impact on operations.”👉🏻 “I think it’s not as important for a CISO to be highly technical as it was 15 years ago.”⏱️Navigate to key timestamps here:00:36 Comprehensive guest Introduction00:40 Professional journey and a discussion on the importance of cybersecurity15:37 What type of skill sets helped you build your career as a CISO?21:40 Do you feel that cybersecurity had a “no” culture 15 years ago?22:43 What’s the most crucial skill a CISO should have?26:12 What are some areas in the CISO role that have changed over the years?29:00 What’s your opinion on the CISO's role as part of the IT organization?30:45 What’s your stance on the CISO role reporting to the IT organization and other departments outside the organization?34:11 What are some helpful tips for individuals who are trying to gain a foothold in the industry?40:41 What is your advice to newcomers and anyone who wants to pursue a career in cybersecurity?43:28 What would you like to have known when you first started your career?49:37 What’s the key factor for success when forming a relationship with vendors?53:45 Closing comments and icebreaker questions📢 Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions #cybersecurityjobmarket #jobmarket #recruitment #specialepisode

March 5, 202435 min

CISO Insiders with Jason Wolpow | Head of Cybersecurity Recruitment at Lawrence Harvey | Episode 80

 In this special episode of CISO Insiders, we welcome Jason Wolpow, the head of cybersecurity recruitment at Lawrence Harvey. Jason Wolpow, together with Ben Ben Aderet, tackle key challenges while sharing key insights on the recruitment side of the cybersecurity industry. This special episode will tackle the following topics:The need for more cybersecurity practitioners.Positive and optimistic trends for the cybersecurity job market this year.Lowering and breaking down the barrier of entry into the cybersecurity industry.Encouraging professionals from all backgrounds to get into cybersecurity.Career progression in Governance, Response, and Compliance (GRC).Here are some highlights from the podcast: ”If you’re listening to this and looking for your first job within cybersecurity, please don’t box yourself out and limit yourself, because there’s so much more.” “At the end of the day, whether you are at the very technical domain of cybersecurity or the less-technical domain, there will still be opportunities to move up and turn into a leader.” “One of the most important things in a CISO’s seat is that board interaction and the executive buy-in.” “Stay persistent. It’s going to be tough; it’s not always going to be fun. Some people do have very high expectations. But stick with it, because it’s very rewarding.”00:36 Guest Introduction and professional journey02:46 Icebreaker questions03:58 What do you do as the head of cybersecurity recruitment?05:20 Biggest failure and key learnings07:42 What is the biggest accomplishment in your career?09:01 What is your high-level view of the cybersecurity industry as of the moment?10:32 What is your view on the barrier of entry to the cybersecurity industry?13:05 What is the most common entry level position that you’re able to recruit for?14:20 What are your thoughts on what would be the career path of a SOC analyst compared to an entry level position in GRC?16:38 Advice to newcomers and anyone that wants to pursue a career in cybersecurity18:21 What are some of the current trends in the cybersecurity industry?20:04 What’s the most crucial skills a CISO should have?22:19 Do CISOs report to an IT organization or outside of it?25:15 What are some key characteristics that you are looking for in different roles as compared to recruiting a CISO?27:11 What is your advice to people taking their first steps into the industry?29:04 What are some helpful tips to individuals that are trying to gain a foothold in the industry?33:02 What’s the best way to connect with you?33:41 Final question and closing comments - If money was not an issue, what would you do with your life? Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions #cybersecurityjobmarket #jobmarket #recruitment #specialepisode

December 19, 202338 min

CISO Insiders with Stephanie Roberts | CISO and VP of Infrastructure at EmployBridge | Episode 79

🔥 In the latest episode of CISO Insiders, we welcome Stephanie Roberts, CISO and VP of Infrastructure at EmployBridge, for an exciting and eye-level conversation about his journey into cybersecurity, advice for young cybersecurity professionals just starting, and how the industry will evolve in future.Highlights👉🏻 ”The biggest concern that we have as CISOs is the gap of talents.”👉🏻 ”It's the team that makes us achieve success.”👉🏻 ”Surrounding myself with experts who know what they are doing is the best resource. Taking advantage of your network is the best way to learn and adapt.”👉🏻 ”Cyber risks are growing day after day. If companies don't have funding in place, bad things can happen.”👉🏻 ”There are so many changes every day in the cyber landscape”Timestamps00:36 Guest Introduction and Professional Journey02:10 Icebreaker questions03:15 Is there one thing you wish you had known before starting your career?05:06 If there are 1-2 things you can recommend to employees out there, what would that be?07:23 Biggest failure and key learnings09:33 What is the biggest accomplishment in your career?11:07 What is your advice to leaders who are currently managing a team?12:12 Advice to younger listeners and anyone who wants to pursue a career in cybersecurity14:00 What are your thoughts on CISO’s role in the IT organization?16:02 What were the best resources that have helped you through your career?17:54 What is one myth about your industry that you want to debunk?20:36 What are the main security concerns of CISOs these days?22:44 Do you think there’s anything we can do as an industry that can help bridge the talent gap?24:46 What are the most important skills that CISOs should have?28:46 What’s next for the cybersecurity industry?29:58 Are you following any CISO on social media these days?31:48 Are there fields in the industry that you consider as innovation?33:35 What would be your strategy in building a professional relationship with a customer you would like to work with?35:00 What is it that you are looking for in a vendor?36:10 Final question and closing comments - If money was not an issue, what would you do with your life?l Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions

December 5, 20231 hr 0 min

CISO Insiders with Dirk Schrader | Field CISO (EMEA) and VP of Security Research at Netwrix Corporation | Episode 78

🔥In the latest episode of CISO Insiders, we welcome Dirk Schrader, Field CISO (EMEA) and VP of Security Research at Netwrix Corporation, for an exciting and eye-level conversation about his journey into cybersecurity, advice for young cybersecurity professionals just starting out, and how the industry will evolve in future.📢Highlights👉🏻 ”Advice to younger listeners and anyone that wants to pursue a career in cybersecurity”👉🏻 ”What are the skills CISOs should have to succeed in the cybersecurity industry?”👉🏻 ”What’s your biggest accomplishment in your career?”⏱️Timestamps00:36 Guest Introduction and Professional Journey04:05 Icebreaker questions04:53 Is there one thing you wish you had known before starting your career?06:31 What were the best resources that have helped you through your career?09:11 Biggest failure and key learnings11:02 Biggest accomplishment13:26 Advice to younger listeners and anyone who wants to pursue a career in cybersecurity15:19 What are the most important skills that CISOs should have?17:48 What position in the company should a CISO report under?19:17 What are your thoughts on CISO’s role in the IT organization?22:22 What is one myth about your industry that you want to debunk?24:31 What are the main security concerns of CISOs these days?27:41 How will the CISO role evolve concerning automation?36:03 What is the biggest attack surface of an organization?44:00 What are your thoughts on cyber resilience?48:10 What are some things that organizations tend to forget in their security posture?53:39 What would be your strategy in building a professional relationship with a customer you would like to work with?56:01 Final question and closing comments - If money was not an issue, what would you do with your life?📢 Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions

November 28, 202332 min

CISO Insiders with Kelly McCracken | Senior VP of Detection and Response at Salesforce | Episode 77

🔥In the latest episode of CISO Insiders, we welcome Kelly McCracken, Senior Vice President of detection and response at Salesforce, for an exciting and eye-level conversation about his journey into cybersecurity, advice for young cybersecurity professionals just starting out, and how the industry will evolve in future.🔎 Highlights:👉🏻 ”Advice to younger listeners and anyone that wants to pursue a career in cybersecurity”👉🏻 ”What are the skills CISOs should have to succeed in the cybersecurity industry?”👉🏻 ”What’s your biggest accomplishment in your career?”⏱️ Timestamps:00:36 Guest Introduction and Professional Journey02:29 Icebreaker questions03:21 Is there one thing you wish you had known before starting your career?04:50 Advice to younger listeners and anyone who wants to pursue a career in cybersecurity07:04 Biggest failure and key learnings09:35 Biggest accomplishment12:01 Advice to beginners on where to start in the cybersecurity industry13:21 What were the best resources that have helped you through your career?15:14 What are your thoughts on CISO's role in the IT organization?17:02 What is one myth about your industry that you want to debunk?18:08 What are the main security concerns of CISOs these days21:11 Are there any specific areas that leaders in the industry should focus on right now?23:10 What are the most important skills that cybersecurity leaders should have?24:54 How will the CISO role evolve in the next 5 years?26:40 Who do you look up to in the industry?27:43 What would you define as innovation in the industry?29:08 What would be your strategy in building a relationship with a customer you would like to work with?31:12 What’s the best way to connect to you online?31:35 Final question and closing comments - If money was not an issue, what would you do with your life?📢Get ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions 

November 14, 202339 min

CISO Insiders with Zlatko Unger (Special Edition) | Former CISO and current GRC wizard at Wiz | Episode 76

🔥 In the latest episode of CISO Insiders, we welcome Zlatko Unger, Former CISO and current GRC wizard at @Wiz, for an exciting and eye-level conversation about his journey into cybersecurity, advice for young cybersecurity professionals just starting, the power dynamics between security leaders and directors in the cybersecurity industry, and other exciting topics in the world of information security.Highlights:👉 ”Why is there friction between the CISO and CIO roles?”👉  ”Should CIOs have veto power over a CISO’s decision?”👉 ”What is one common myth about cybersecurity from the perspective of the board of directors?”⏱️Timestamps00:36 Guest Introduction and Professional Journey01:10 Icebreaker questions02:53 What are the differences between the CISO and CIO roles?05:40 Why is there friction between the CISO and CIO roles?07:17 What are the challenges between the functions of the CISO and CIO roles?09:44 Why should directors be interested in CISOs as board members?12:56 Who are the stakeholders that should run the IT domain?16:48 Why is it not effective for a CISO to report to a CIO?18:46 Should CIOs have veto powers over a CISO’s decision?21:06 How would hiring a CISO revolutionize the industry?24:19 What would it take to change the current status quo of the CISO’s relation to the company’s board?28:36 What are some key ways to initiate a shift in the organization’s structure?32:25 What is one common myth about cybersecurity from the perspective of the board of directors?38:36 Closing commentsGet ahead in your professional journey and gain valuable cybersecurity insights.Follow GRSee Consulting and GRSee University on LinkedIn to stay updated.#cybersecurity #podcast #careeradvice #cybersecurityawareness #cybersecuritycommunity #cybersecurity #cybersecuritypodcast #cybersecuritysolutions