SilverSky: The Human Layer

SilverSky

Cybersecurity is built on trust, and trust starts with people. The SilverSky Podcast gives customers, partners, and our broader community a closer look at the people behind SilverSky. Each episode features candid conversations with team members, leaders, partners, and customers about their career paths, experiences, lessons learned, and the relationships that shape the work we do every day. This is not a technical briefing or a sales conversation. It is a people-first series about the individuals, perspectives, and values behind a long-standing cybersecurity partner. Learn more about us at https://www.silversky.com/

Episodes

  1. Oct 16

    The Human Layer: Episode 6 | Jan Masters: Inside the Mind of an Ethical Hacker

    What does an ethical hacker actually do, and how does penetration testing help organizations find cybersecurity risks before attackers do? In this episode of The Human Layer, host Bruce Wirt, Chief Revenue Officer at SilverSky, sits down with Jan Masters, Head of Penetration Testing at SilverSky, to explore ethical hacking, penetration testing, security research, AI in cybersecurity, and the risks hidden inside the technology businesses use every day. Jan shares his unconventional path into cybersecurity, from studying game development and working in IT support to building a career focused on identifying vulnerabilities and helping organizations understand their real-world exposure. He also explains why the word “hacker” is not inherently negative. To Jan, the hacker mindset is about curiosity, creativity, logical thinking, and finding new ways around difficult problems. The conversation explores how penetration testers evaluate weaknesses across networks, applications, connected devices, and business technology. Jan and Bruce discuss risks associated with printers, smart devices, mobile applications, passwords, and connected infrastructure, along with the constant balance between security, usability, and convenience. They also examine the growing role of artificial intelligence in cybersecurity, including both its potential and the security questions organizations need to consider as AI systems become more capable and autonomous. Jan closes with an important point for organizations evaluating cybersecurity and penetration testing services. Automated tools can provide valuable information, but strong security testing still requires experienced people who can interpret findings, understand context, and validate what the technology is telling them. If you have ever wondered how ethical hackers think, what penetration testing actually looks for, or where hidden cybersecurity risks may exist inside everyday technology, this episode offers a look behind the curtain. Listen to The Human Layer on YouTube, Spotify, Apple Podcasts, Amazon Music, iHeartRadio, and wherever you get your podcasts. Important Links 🎙️ The Human Layer Podcast: https://silversky.com/human-layer-podcast 🌐 SilverSky: https://silversky.com 📊 Cyber Maturity Assessment: https://hubs.la/Q04Bh-tq0 Follow or subscribe on your preferred platform for future episodes. Music licensed through Soundstripe. Code: NIBFL12KGNJSMA4G

    The Human Layer: Episode 6 | Jan Masters: Inside the Mind of an Ethical Hacker

  2. Sep 29

    The Human Layer: Episode 5 | Alina DaSilva: The Human Side of Security Operations

    Meet Alina DaSilva Security Services Delivery Lead at SilverSky, whose path to cybersecurity started somewhere very different: the medical field. In this episode of The Human Layer, host Bruce Wirt sits down with Alina to talk about the unexpected turns that brought her into cybersecurity, what it means to bridge the gap between customers and security operations, and why some of the hardest security challenges still come down to people. The conversation moves from social engineering and Zero Trust to running, mountain biking, creative outlets, career reinvention, and what life actually looks like for the people working behind the scenes in cybersecurity. It is another candid look at the people behind SilverSky. Their paths, their personalities, and the experiences that shape how they approach their work. Listen to The Human Layer on Spotify, Apple Podcasts, YouTube, Amazon Music, iHeartRadio, or wherever you get your podcasts. Important Links: 🎙️ The Human Layer Podcast: https://silversky.com/human-layer-podcast 🌐 SilverSky: https://silversky.com 📊 Cyber Maturity Assessment: https://cyber-maturity.com/p/silversky

    The Human Layer: Episode 5 | Alina DaSilva: The Human Side of Security Operations

  3. Sep 16

    The Human Layer: Episode 4 | Jessica Huellmantel: Building Customer Relationships That Last

    What does it take to build lasting customer relationships in cybersecurity? In Episode 4 of SilverSky: The Human Layer, host Bruce Wirt, Chief Revenue Officer at SilverSky, sits down with Jessica Huellmantel, a customer success leader who has spent more than 21 years growing alongside SilverSky and its customers. Jessica shares her journey from becoming the company’s first Technical Account Manager to helping lead customer success and account management today. The conversation explores what it means to earn trust over time, support customers through change, and keep relationships personal as an organization grows. Bruce and Jessica discuss why listening is the foundation of meaningful customer conversations, how SilverSky’s customer success team is expanding to create more connection and visibility, and why the best opportunities come from understanding the customer’s real needs, not pushing a product. They also step outside of work to talk about Jessica’s two golden retrievers, her daily walking goal, and life as a proud mom of two sons, including a high school football kicker with college aspirations. Whether you are a SilverSky customer, partner, or employee, this episode offers a closer look at the people, relationships, and care behind the customer experience. In this episode: Jessica’s 21-year journey with SilverSkyBuilding long-term customer relationshipsListening before recommending a solutionGrowing customer success without losing the personal connectionLeadership, training, and supporting a growing teamLife outside of work, from golden retrievers to college football goalsThe human side of customer success Take SilverSky’s free Cyber Maturity Assessment at SilverSky.com and learn how your organization can strengthen its security and compliance posture. Helpful Links: SilverSky Cyber Maturity Assessment SilverSky on LinkedIn Subscribe to SilverSky: The Human Layer on your preferred podcast platform.

    The Human Layer: Episode 4 | Jessica Huellmantel: Building Customer Relationships That Last

  4. Aug 31

    The Human Layer: Episode 3 | Jake Smallwood: From MSP Owner to Cybersecurity Sales Engineer

    What does it take to build a successful career in IT, cybersecurity, and sales engineering? In Episode 3 of SilverSky: The Human Layer, host Bruce Wirt, Chief Revenue Officer at SilverSky, sits down with Jake Smallwood, Sales Engineer and cybersecurity professional, to discuss his journey from running a Managed Service Provider (MSP) to helping organizations improve their cybersecurity posture through managed security services and security consulting. Jake shares how early experiences in IT support, systems administration, network management, and entrepreneurship prepared him for a career in cybersecurity. The conversation explores the transition into sales engineering, the skills required to bridge technical expertise with business outcomes, and why listening to customers is one of the most important skills in technology and security leadership. Bruce and Jake also discuss cybersecurity compliance, risk management, cyber maturity, security operations, and the growing overlap between telecommunications, IT infrastructure, and managed security services. Whether you're a cybersecurity professional, MSP owner, aspiring sales engineer, or technology leader, this episode provides practical career advice and real-world lessons from years in the industry. In this episode: Building a career in IT and cybersecurityManaging and growing an MSPTransitioning into sales engineeringCybersecurity compliance and risk managementCustomer-focused security consultingIT leadership and career developmentThe human side of cybersecurity Take SilverSky's free Cyber Maturity Assessment at SilverSky.com and learn how your organization can strengthen its security and compliance posture. Helpful Links: Learn more about SilverSky Take the Cyber Maturity Assessment Connect with SilverSky on LinkedIn Subscribe to SilverSky: The Human Layer on your preferred podcast platform.

    The Human Layer: Episode 3 | Jake Smallwood: From MSP Owner to Cybersecurity Sales Engineer

  5. Aug 17

    The Human Layer: Episode 2 | EJ Orsini Jr.: Leadership, Curiosity, and the People Behind the SOC

    In Episode 2 of SilverSky: The Human Layer, host Bruce Wirt sits down with Efrain “EJ” Orsini Jr., Director of Security Operations, to explore the experiences that shaped how he leads SilverSky’s Security Operations Center. EJ traces his path from New Jersey and 22 years of Army Reserve service to cell phone sales, IT, and cybersecurity leadership. He shares why adaptability, effort, and a clear sense of purpose can matter more than a perfect résumé, and how those principles influence the way he develops analysts and builds teams. The conversation also explores the people behind managed detection and response. EJ explains why effective security operations require more than automation, how analysts apply human judgment to meaningful activity, and why security and compliance must work together. Plus, EJ shares a lesser-known part of his story involving karate, a second-degree black belt, and an unexpected national championship. Helpful Links: Learn more about SilverSky Take the Cyber Maturity Assessment Connect with SilverSky on LinkedIn Subscribe to SilverSky: The Human Layer on your preferred podcast platform.

    The Human Layer: Episode 2 | EJ Orsini Jr.: Leadership, Curiosity, and the People Behind the SOC

  6. Aug 3

    The Human Layer: Episode 1 | Clark Easterling: Twenty Years of Change, Growth, and SilverSky

    In the first episode of SilverSky: The Human Layer, host Bruce Wirt sits down with Clark Easterling, SilverSky’s Vice President of Sales Operations, for a conversation about the people, experiences, and relationships behind the work. Clark has spent nearly two decades at SilverSky, serving across marketing, product marketing, contracts and pricing, and sales operations. In this episode, he shares how his path moved from nuclear engineering to technology, what it means to improve the customer experience behind the scenes, and why strong processes matter when customers and partners are relying on SilverSky to deliver. The conversation also goes beyond the business. Bruce and Clark talk about growing up in South Carolina, pro wrestling, ski instruction, family, leadership, hard-earned lessons, and a hunting story that proves some ditches are better left untested. This episode is a closer look at one of the people who helps keep SilverSky moving, both in front of customers and behind the scenes. Helpful Links: Learn more about SilverSky Take the Cyber Maturity Assessment Connect with SilverSky on LinkedIn Subscribe to SilverSky: The Human Layer on your preferred podcast platform.

    The Human Layer: Episode 1 | Clark Easterling: Twenty Years of Change, Growth, and SilverSky

  7. Season 1 Trailer

    SilverSky: The Human Layer Season 1 Trailer

    Cybersecurity is built on trust, and trust starts with people. SilverSky: The Human Layer is a people-first podcast from SilverSky, created to give customers, partners, employees, and our broader community a closer look at the individuals behind the work we do every day. Hosted by Bruce Wirt, Chief Revenue Officer at SilverSky, the series features candid conversations with SilverSky team members, leaders, partners, and customers about career paths, lessons learned, memorable stories, and the relationships that shape how we support the organizations we serve. In our first episode, Bruce sits down with Clark Easterling, VP of Sales Operations, to talk about Clark’s nearly 20-year journey with SilverSky, the experiences that shaped his career, and one unforgettable hunting story that became part of company lore. This is not a technical briefing or a sales conversation. It is a closer look at the people, perspectives, and values behind a long-standing cybersecurity partner. Follow SilverSky: The Human Layer and listen for Episode 1, launching Monday, August 3. Learn more about SilverSky.

  • 1 Trailer
    6 Episodes

Trailer

About

Cybersecurity is built on trust, and trust starts with people. The SilverSky Podcast gives customers, partners, and our broader community a closer look at the people behind SilverSky. Each episode features candid conversations with team members, leaders, partners, and customers about their career paths, experiences, lessons learned, and the relationships that shape the work we do every day. This is not a technical briefing or a sales conversation. It is a people-first series about the individuals, perspectives, and values behind a long-standing cybersecurity partner. Learn more about us at https://www.silversky.com/

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