by 909Exec Podcast
The 909Exec Podcast Hosted by Den Jones, CEO of 909Cyber, this podcast dives into real-world leadership with insights from top execs across industries. From startups to global giants, Den brings wit, wisdom, and his signature Scottish flair to every episode—helping you lead smarter, grow faster, and avoid the pitfalls.
Language
🇺🇲
Publishing Since
9/12/2024
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June 21, 2026
<p><strong>Introduction Summary</strong></p><p>Hosted by CEO Den Jones, "909 Exec" is a leadership podcast from 909 Cyber. Jones uses his 30+ years of enterprise security experience at companies like Adobe and Cisco to help executives navigate risk and transformation. Episode 63 features Nightfall AI co-founder and CEO Rohan Sathe for a deep dive into Data Loss Prevention (DLP).</p><p><br></p><p><strong>Main Topics Covered</strong></p><ul><li><p><strong>Entrepreneurial Journey:</strong> Sathe discusses his Silicon Valley roots and transition from the Uber Eats founding team to a cybersecurity founder.</p></li><li><p><strong>Consumer-Grade Enterprise Software:</strong> Sathe applies lessons from Uber Eats—building scalable products for low-switching-cost markets—to drive Nightfall’s enterprise product quality.</p></li><li><p><strong>Fundraising Strategy:</strong> Outlining Nightfall’s $65M total raise, Sathe emphasizes prioritizing investors who offer cybersecurity expertise and founder empathy over just capital.</p></li><li><p><strong>Flaws of Legacy DLP:</strong> After interviewing ~100 CISOs in 2018, Sathe found legacy tools were noisy, unpopular, and unsuited for modern cloud apps like Slack and Google Drive.</p></li><li><p><strong>Skepticism & Pain Points:</strong> Jones details his historical skepticism of DLP, citing lost employee productivity, high false-positive rates, blind spots, and a heavy reliance on user-driven classification.</p></li><li><p><strong>Design Principles:</strong> Nightfall aims to make DLP "invisible" to end-users unless an incident occurs. Jones relates this to his view that security should be "invisible, invincible, and inexpensive."</p></li><li><p><strong>Frictionless Architecture:</strong> Unlike SASE vendors that rely on latency-heavy network proxies, Nightfall targets optimal insertion points to eliminate user workflow delays and efficiently handle false positives.</p></li><li><p><strong>AI-Driven Risk Modeling:</strong> Replacing legacy regex rules with neural-network NLP and computer vision, Nightfall uses a comprehensive risk model evaluating identity, data lineage, and destinations to identify true incidents.</p></li><li><p><strong>Board-Level AI Concerns:</strong> As boards push for rapid AI adoption, AI data protection is now critical. This demands strict governance over autonomous agents operating at machine speed.</p></li><li><p><strong>Expanding Customers:</strong> Initially successful with tech-forward health and fintech companies, Nightfall's customer base has expanded into traditional sectors like manufacturing due to new AI security needs.</p></li><li><p><strong>Deployment & Value:</strong> Nightfall ensures rapid deployment via lightweight endpoint agents and system APIs (avoiding proxies). It integrates directly with SaaS apps and AI platforms to track prompts and agent actions.</p></li><li><p><strong>Managing Data:</strong> Nightfall tracks data movement between corporate and personal environments, including AI tools like ChatGPT. It can monitor or block personal AI usage and track file lineage to determine corporate ownership.</p></li><li><p><strong>Policy Enforcement:</strong> The platform uses customizable policies to block risky actions, present user justification prompts, and offer optional bypasses tailored to organizational philosophies.</p></li><li><p><strong>Startup Strategy & Compliance:</strong> Both agree expensive conference booths yield low ROI, favoring targeted events like dinners. Jones advises pursuing compliance primarily to unblock deals, noting it does not equate to actual security.</p></li><li><p><strong>Selling to CISOs:</strong> Acknowledging that CISOs are overwhelmed with pitches, they emphasize humility, understanding the customer's specific problems, and building long-term trust.</p></li><li><p><strong>Closing Reflections:</strong> Sathe admits he initially underestimated the importance of go-to-market strategies in cybersecurity. He warns that autonomous AI agents will permanently alter security paradigms. Jones concludes by clarifying the episode was unpaid and commending Sathe for changing his negative perception of DLP.</p></li></ul><p><br></p>
June 9, 2026
<p>In this episode of 909 Exec, host Den Jones sits down with longtime friend and mentor Toni Vanwinkle, Adobe’s leader for Digital Employee Experience and co-chair of AI, to explore how technology, disruption, and human-centered leadership are reshaping the future of work. </p><p><br></p><p>Toni shares her nonlinear “career lattice” journey from aspiring artist to finance professional, then into consulting and large-scale enterprise transformations at Cisco, before spending 16 years at Adobe in multiple roles. Along the way she discovered a passion for technology as a powerful way to solve business problems, implementing early automations and ERP systems, and learning how organizational change management is essential to bringing people along in any transformation.</p><p><br></p><p>She opens up about pivotal personal decisions—like leaving a high-stress role to pursue consulting so she could prioritize starting a family—and how she and her husband redesigned their careers to create a sustainable “container” for work and parenting. Toni explains why you can have it all, just not all at the same time, and how aligning career moves with life needs and values has guided her path. </p><p><br></p><p>Den and Toni dive into the trap of “work, work, work” in your 20s, and why so many professionals are blind to the need to prioritize their physical, financial, and spiritual health, as well as their broader sense of purpose. Toni encourages people to see themselves as multidimensional, drawing on her own artistic background to show how creativity can fuel even highly technical roles. </p><p><br></p><p>The conversation then turns to the future of work and the transformative impact of AI. Toni outlines three key questions she uses to reimagine work: Do we still need to do this work? How can technology augment us as a thought partner? And what can we safely automate and delegate to machines? She envisions a future where humans provide context, creativity, and critical thinking, while AI accelerates consistency, reasoning, and problem-solving. </p><p><br></p><p>As co-chair of AI at Adobe, Toni discusses how the company is embedding AI into products while maintaining a foundation of trust—focusing on security, ethics, and bias in models—and why educating employees on both AI proficiency and “human in the loop” responsibility is critical. She emphasizes that humans remain accountable for outcomes, even when AI is involved, and notes that bad actors are also using AI, which raises the stakes for security. </p><p><br></p><p>Den and Toni compare the AI boom to the early web era, agreeing that AI will dwarf previous technology shifts in impact. They explore how AI is already accelerating work—from building internal tools and quizzes in minutes instead of weeks, to rethinking build-vs-buy decisions for enterprise software—while acknowledging that large-scale enterprises still need robust data, governance, and security layers. </p><p><br></p><p>Throughout, they return to themes of wellbeing and sustainability in high-intensity operational roles, likening security and operations leaders to first responders. Toni argues that leaders must actively “bench” exhausted team members and continually reassess what they value—impact, relationships, spiritual and physical health, or time outdoors—so they can make conscious tradeoffs instead of unconsciously sacrificing their lives to work. </p><p><br></p><p>To close, Toni shares what recharges her outside of work: time at the beach in any weather, the sense of wonder she finds in her garden, and the visceral energy she gets from live music. Den adds his own love of gardening, wine, and concerts, underscoring their shared belief that a rich life outside the office fuels better leadership inside it. </p>
May 30, 2026
<p>This episode of <strong>“909 Exec,”</strong> hosted by 909 Cyber CEO Den Jones, explores where cybersecurity meets business strategy. Guest <strong>Cassio Goldschmidt</strong>, CTO of Reflex, discusses his career evolution and the launch of Reflex Security.</p><ul><li><p><strong>Early Tech Roots:</strong> Discovered computers as a teenager in Brazil, which naturally led to a computer science degree.</p></li><li><p><strong>Silicon Valley:</strong> Moved to California to join Cisco just before the internet boom.</p></li><li><p><strong>Initial Projects:</strong> Worked on industrial automation in Brazil, followed by PC configuration (“Splice”) and early video conferencing initiatives at Cisco.</p></li></ul><ul><li><p><strong>CISO Success:</strong> Effective Chief Information Security Officers (CISOs) need strong interpersonal skills and business alignment, not just technical expertise.</p></li><li><p><strong>Role Differences:</strong> A Business Information Security Officer (BISO) acts as a consultant across shared business units. In contrast, a CISO owns the resources and integrates deeply into daily operations.</p></li><li><p><strong>Community Networking:</strong> Engaging in communities like OWASP and BSides is essential for ongoing learning, collaboration, and building career resilience.</p></li></ul><ul><li><p><strong>A New Challenge:</strong> After guiding ServiceTitan's security program from its early days through an IPO, Cassio left his CISO role to satisfy his engineering and inventive mindset.</p></li><li><p><strong>Founding Reflex:</strong> He launched Reflex (Reflect Security) to build a truly innovative solution for incident preparedness.</p></li></ul><ul><li><p><strong>The Problem:</strong> Traditional tabletop exercises are often static, PowerPoint-driven, and lack engagement for modern technical leaders.</p></li><li><p><strong>The Solution:</strong> Reflex is an AI-driven platform that runs dynamic, OSINT-tailored tabletop simulations under realistic pressure.</p></li><li><p><strong>Behavioral Tracking:</strong> It detects human factors like panic, mistakes, and cognitive overload to generate fact-based reports rather than opinion-based assessments.</p></li><li><p><strong>Platform Flexibility:</strong> Reflex can run combined or separate tabletops for tech and executive teams, model different personality types, and deploy rapidly.</p></li><li><p><strong>Remote Integration:</strong> Natively supports Zoom, Google Meet, and Teams. It uses AI agents to co-facilitate and ask role-specific questions.</p></li><li><p><strong>Market Disruption:</strong> Highly cost-effective and scalable, Reflex allows for frequent, targeted tabletops rather than expensive, one-off traditional engagements.</p></li></ul><ul><li><p><strong>Target Audience:</strong> Ideal for large enterprises (like Cisco) and private equity firms needing high-quality, frequent tabletops across multiple portfolios on a budget.</p></li><li><p><strong>Security Training:</strong> Provides an immersive alternative to standard security awareness training by actively engaging users in common scenarios like MFA bypasses or USB risks.</p></li><li><p><strong>Future Vision:</strong> Enables organizations to track measurable team improvement over time, helping meet strict compliance and third-party preparedness expectations.</p></li></ul><ul><li><p><strong>Financial Status:</strong> Backed by professional VCs, Reflex emerged from stealth in January after a year of development. It is pre-Series A but has a secure, multi-year financial runway.</p></li></ul><p>Den and Cassio advise aspiring leaders to know their “why” and pursue disruptive strategies rather than the status quo. Reflex is highlighted as a low-friction, risk-reducing alternative for budget-constrained CISOs. The episode concludes by celebrating the partnership between 909 Cyber and Reflex, emphasizing a shared goal of revolutionizing organizational tabletop exercises.</p><p><br></p>
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The 909Exec Podcast
Hosted by Den Jones, CEO of 909Cyber, this podcast dives into real-world leadership with insights from top execs across industries.
From startups to global giants, Den brings wit, wisdom, and his signature Scottish flair to every episode—helping you lead smarter, grow faster, and avoid the pitfalls.
This podcast updates daily.
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