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Audience 1st

Published by Dani Woolf

  • Marketing
  • Business
  • Technology

Welcome to Audience 1st. A podcast for tech marketers looking to break out of the echo chamber to better understand their audience and turn them into loyal customers. Every week, Dani Woolf is having brutally honest conversations with busy tech buyers about what really motivates them, the things they hate that vendors do, and what you can do about it. You’ll get access to practical information on how to build authentic relationships with your audience, listen to and talk with your buyers, and apply real customer insights to your strategies and tactics. You owe it to the world to unmute your mic. Are you ready? audience1st.substack.com

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Recent episodes

The latest episodes published to this podcast’s own RSS feed. Titles and descriptions are the publisher’s.

  1. What OpenClaw Going Sideways Reveals About How Humans Interact with Technology from Audience 1st, opens in a new tab

    Apr 10, 202643 min

    Alex Yampolskiy walked back into my studio, sat down, complimented the pillow, and then spent the next hour telling me things that kept me up that night. It hasn't been long since our first conversation. But in the weeks between sessions, an open-source AI agent called OpenClaw went viral and then went sideways. Tens of thousands of people rushed to install a personal AI assistant that connects to their email, calendar, WhatsApp, and terminal. Almost nobody thought about security before they hit deploy. SecurityScorecard's research team scanned the entire internet and found over 40,000 exposed instances. No authentication. No encryption. Named in ways that let you identify the person and the company they worked for. Hackers found them before the organizations did. In this episode, we unpack what OpenClaw reveals about how humans interact with technology and why the problem is much bigger than one tool. AY explains why people click first and think second in the digital world, even though they'd never walk into a dark alley without looking over their shoulder. He describes AI agents as ephemeral interns with root access who disappear before you can fire them. He walks through why the speed of exploitation has dropped from days to microseconds and why human-speed defense against machine-speed offense is no longer viable. We get into territory that most cybersecurity conversations avoid. AY is blunt about AI budgets exploding while security budgets stay flat and what that means for CISOs being asked to govern technologies they had no say in adopting. He tells me that most third-party risk programs operate one day a year, leaving 364 days where nobody is verifying anything. He walks me through Security Scorecard's maturity framework from static, point-in-time assessments to continuous monitoring to threat-informed detection and response and is honest about where most organizations actually sit on that curve versus where they think they sit. The gap between those two points is where the real risk lives. He makes the case that compliance and security are best friends, not twins, and that the forcing function of regulation is often the only thing that unlocks budget. He explains why the Ukrainians deliberately hacked their own infrastructure before the Russians could. And he says, plainly, that if you can't afford the secure tools, you accept the risk. No soft landing. Listen in and enjoy. A special thanks to our friends at Security Scorecard for partnering with us to tell this story. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  2. Why Human Risk Will Define the Next Decade of Security from Audience 1st, opens in a new tab

    Mar 18, 202649 min

    Three decades. Billions of dollars in security investment. And the human element still sits behind 68% to 72% of every breach that happens. If that statistic does not make you uncomfortable, you have probably been in this industry long enough to have accepted it as inevitable. Masha Sedova has not accepted it, and this episode is the result of a career spent refusing to. Masha co-founded Elevate Security, built it into the leading human risk management platform in the space, and watched it get acquired by Mimecast - where she now leads human risk strategy and product across a portfolio that combines email security, DLP, collaboration security, and behavioral risk intelligence under one roof. She is one of the most rigorous thinkers working at the intersection of people and security, and this conversation left me genuinely rattled in the best possible way. We talk about what human risk management actually is and why calling it a rebrand of security awareness is a disservice to both categories. We get into the 8/80 rule - the finding that 8% of your workforce is responsible for 80% of your incidents - and what it means for how security budgets should actually be allocated. We cover the four personas framework, the open ecosystem bet, the board conversation, and the cultural debt that the phrase 'humans are the weakest link' has accumulated over thirty years. I push back where I think the industry has not fully reckoned with what it is building, and Masha pushes right back. If you work in cybersecurity in any capacity - whether you are a CISO, a founder, an investor, or a marketer trying to understand what your buyers actually care about - this episode will change how you think about the human element problem. Listen and enjoy. A special thanks to our friends at Mimecast for partnering with us to tell this story. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  3. The Kid Who Googled "How to Become a Hacker" and Ended Up Wrecking Real Ones from Audience 1st, opens in a new tab

    Mar 1, 202636 min

    John Hammond was a kid who Googled "how to become a hacker" and took it seriously. He learned Python, found his way into the Coast Guard Academy, and remembers squaring down a stairwell at two in the morning - rigid military posture, full indoctrination protocol - vibrating with excitement because he was about to sit next to smart people and solve security problems for a living. That visceral, middle-of-the-night certainty became the foundation of everything that followed. Today he's a principal security researcher on the Adversary Tactics team at Huntress, employee number twenty-eight at a company that's now over six hundred people. He's also one of the most recognized cybersecurity educators on the internet, producing hour-long exploit deep dives on YouTube that get more genuine engagement than most vendors' entire content budgets combined. In this episode, John talks about why the cybersecurity industry is stuck on a treadmill it may never get off and whether the business model actually depends on that treadmill keeping pace. He explains why Huntress is deliberately slow about integrating AI into their human-led SOC and why that uncertainty is more credible than the confident claims coming from thousands of other cybersecurity vendors in the space. We also get into territory that most cybersecurity conversations gloss over. John makes the case that the security awareness gap isn't informational - the information exists, he's made it free on YouTube - it's motivational, and most training programs are built around what the security team thinks is important rather than what the end user actually cares about. He talks about why checklists function as a ceiling on curiosity, and why the discoveries that actually matter are the ones that never make it onto the procedure document. And he gets real about burnout - the arc from obsessive passion to unsustainable output that the industry celebrates in keynotes and ignores in its operational expectations. There's a moment near the end where I asked him to describe Huntress in three words and he gave me an internal mantra - ethical badasses - that says more about how the company thinks about culture as a competitive weapon than any mission statement ever could. This is a conversation about what happens when someone who never optimized for credibility becomes one of the most credible voices in the room. Listen and enjoy. A special thanks to our friends at Huntress for partnering with us to tell this story. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  4. The PhD Cryptographer Who Bet His Career on a Lukewarm Idea and Succeeded from Audience 1st, opens in a new tab

    Feb 28, 202645 min

    Aleksandr Yampolskiy was doing everything right. He had the tools, the budget, the processes - the full security stack humming along at the e-commerce company where he served as CISO. Then one routine vendor integration blew the whole thing open. Unencrypted credit card data from other customers, just sitting there, inside a platform that had been rubber-stamped by a Big Four firm. In that moment, he realized something most security leaders spend their careers trying not to think about: you can do everything right and still lose your job because someone else didn't. That scar became SecurityScorecard . But here's where the story gets interesting. When Aleksandr, or AY - as he introduced himself when joining me in my studio, started telling people in 2013 that he wanted to quantify cyber risk the same way credit scores quantify financial risk, nobody was excited. The reactions ranged from "that's impossible" to a polite shrug. Most founders would have taken that as a signal to pivot. Alex took it as proof he was early enough to matter. In this episode, we go deep. We talk about why the status quo, not a named competitor, is the most dangerous thing your sales team will ever face. AY tells the story of twenty buyers who all said "I love it, I'll buy it" and then every single one of them disappeared when he came back with the finished product. (Oh, how I resonate deeply with this pain.) He explains how a pediatrician named Dr. Virginia Apgar, who saved tens of thousands of newborns with a simple scoring system, became the intellectual blueprint for how Security Scorecard thinks about risk. And he gets honest about hiring decisions that went wrong because he ignored a gut feeling he couldn't quite articulate at the time. We also get into territory that most cybersecurity podcasts don't touch. AY talks about boards adopting AI to impress Wall Street while CISOs scramble to secure shadow deployments nobody authorized. He walks through why 150 companies control ninety percent of the global attack surface and what that means for everyone else. He makes the case that quantum computing will be a Y2K-scale migration problem much sooner than the industry wants to admit. And he shares a question from his company advisor that I think every GTM leader needs to sit with: Who do you want your customers to become? This is a conversation about how a scientist thinks about risk, why the language gap between the SOC and the boardroom is an actual vulnerability, and what it really takes to build something that changes how an industry operates. Listen in and enjoy. A special thanks to our friends at SecurityScorecard for partnering with us to tell this story. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  5. How to Stop Falling for Fake Cyber Threat Exposure Management (CTEM) Claims from Audience 1st, opens in a new tab

    Dec 19, 202543 min

    Every vendor in exposure management now says they do CTEM. Nick Lantuh's response: "You don't even know what you're talking about." This episode with Nick Lantuh (CyberProof) and Amy Chaney (Citibank) breaks down how a methodology became a meaningless marketing term and how buyers can fight back. The reality check: CTEM requires connecting vuln scanning, endpoint, SIEM, cloud, email, network—not just one of them Adding CAASM or external attack surface management doesn't make you a CTEM vendor Most organizations doing "CTEM" are actually using spreadsheets and manual threat intel fusion Why services-led beats platform-first (60x revenue growth proved it) The disingenuity problem: vendors spray the term, buyers have to unpack it Amy's evaluated these claims at the world's largest banks. Nick built the solution that actually connects the pieces. Together, they arm you with the filter. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  6. Why Are You Outsourcing Buyer Intimacy to Gartner?!? from Audience 1st, opens in a new tab

    Dec 5, 202543 min

    The Gartner debate keeps resurfacing on LinkedIn. Skeptics vs. pragmatists vs. the "it depends" crowd. Same arguments. Same camps. Same circular conversation. Everyone's missing the point. After having hundreds of direct conversations between vendors and CISOs, I've come to a controversial conclusion: The analyst relations industry exists because marketers don't want to do the hard work of actually understanding their buyers. In this episode, I'm going deep on what no one's willing to say: How buyer insight gets distorted through seven (at least) layers of interpretation before it reaches your strategy. By the time Gartner's "insight" hits your roadmap, it's a game of telephone. Vendors expect Gartner to generate pipeline. It generates awareness. That awareness doesn't convert. And the "justification" use case? I don't buy it anymore. I'll tell you what CISOs actually say. Gartner has become a shortcut to avoid the uncomfortable work of direct buyer relationships. More surprisingly, the analysts aren't doing the deep work either. You are the product, not the customer. AI is commoditizing surface-level insight. But the deep nuance, the psychology, the politics, the unspoken objections, that still requires human connection. The differentiator is becoming more human, not less. What to do instead. How to build buyer intimacy as a core competency. Why the vendors who win will be the ones who stop outsourcing the most important work in marketing. This episode isn't about whether Gartner is good or bad. It's about a harder question: How well do you actually know your buyer? If the honest answer is "not deeply enough", Gartner isn't your problem. If you're a cybersecurity founder, marketer, or GTM leader wondering who has even the smallest inkling or intuitive feeling deep down inside that your Gartner investment isn’t worthwhile, this one's for you. Connect with me on LinkedIn Learn more about CyberSynapse This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  7. From Cost Center to Growth Driver: The CFO’s Playbook for Cloud Security ROI from Audience 1st, opens in a new tab

    Jun 6, 202547 min

    For years, security has been treated as a necessary evil - a budget line item that CFOs approve without truly understanding its business impact. But what if cloud security could be a revenue driver, an efficiency enabler, and a cost-saving powerhouse? In this episode, Dani Woolf sat down with Chris Thomas, Chief Revenue Officer at AlgoSec, to break down how CFOs should really evaluate cloud security investments, not just as a defensive measure, but as a business accelerator. They dove into the cost of inaction, the inefficiencies draining budgets, and the financial case for security automation - all from a CFO’s perspective. If you’re still treating security as an overhead cost, this conversation will change the way you think about it. To get a demo of AlgoSec, visit: https://www.algosec.com/lp/request-a-demo This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  8. Why the vCISO Model Is More Than a Stopgap for Organizations Looking for Security Leadership from Audience 1st, opens in a new tab

    May 30, 202550 min

    In this milestone 100th (and birthday!) episode of Audience 1st Podcast, Dani Woolf is joined by veteran cybersecurity leader David Doyle from DirectDefense for a brutally honest conversation about what’s broken in today’s security leadership models and how the rise of the vCISO is more than just a stopgap. Together, they unpack the myths, power dynamics, and misaligned expectations that drive burnout, stall progress, and keep companies from building real security maturity. This episode is a blueprint for cybersecurity executives, CISOs, and vCISOs who are serious about designing resilient organizations that can lead through complexity. You’ll Learn: 1. The real reason CISOs are burning out and why it’s not just about stress 2. How most orgs misunderstand the vCISO role (and end up wasting budget) 3. When to bring in a vCISO and how to avoid hiring the wrong one 4. Why CISOs and vCISOs should be tag-teaming, not competing 5. How to measure progress beyond compliance and build a culture of strategic leadership 6. What makes a good vCISO indispensable, not replaceable Subscribe & Follow: Follow Audience 1st wherever you get your podcasts Connect with Dani Woolf on LinkedIn Learn more about CyberSynapse and qualitative buyer research This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  9. The GTM Gauntlet in Cybersecurity: What We're Still Getting Wrong | Authenticated by Confide from Audience 1st, opens in a new tab

    May 23, 202557 min

    In this special episode of Authenticated, Confide brings together a powerhouse panel of security operators, marketers, and founders to dissect the brutal realities of go-to-market in cybersecurity. From failed conference booth investments to relationship-first community building, this conversation goes deep on why most vendors still miss the mark, and what it actually takes to build trust with today’s security buyers. Whether you’re a CISO, product marketer, founder, or GTM leader in security, this episode cuts through the noise with raw, unfiltered truths about what works, what backfires, and where the future of security GTM is headed. Key Themes We Cover Why cybersecurity is one of the hardest GTM motions in tech—period The myth of the CISO as the sole buyer (and who actually influences decisions) How real community works—and why fake ones backfire Why founder curiosity and customer obsession are the biggest predictors of success The buyer psychology behind trust, timing, and transference What not to do at RSAC (and how to rethink your event strategy) The role of failure, redemption, and authentic messaging in building credibility Tactical ways to break through cynicism and engage skeptical security practitioners Subscribe & Follow: Follow Audience 1st wherever you get your podcasts Connect with Dani Woolf on LinkedIn Learn more about CyberSynapse and qualitative buyer research This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  10. Cognitive Risk, Neurodivergence, and the Unspoken Realities of Security Leadership from Audience 1st, opens in a new tab

    May 16, 202536 min

    In this episode of Audience 1st Podcast, Dani Woolf sits down with Val Popke to explore the unspoken human dimensions of cybersecurity leadership. Val, a veteran, assurance leader, and self-described “Wandering Cyber Vulva,” challenges the industry’s prevailing narratives around hiring, communication, inclusion, and resilience. The discussion goes beyond traditional security frameworks to uncover the cognitive and cultural risks impacting practitioners at all levels. Listeners will walk away with a deeper understanding of why burnout, disconnect, and distrust are systemic, not personal, and how security leaders must evolve to lead in environments of increasing complexity, diversity, and psychological strain. Key Themes: Why psychological safety and cognitive clarity are prerequisites for functional security operations. How the industry’s hidden majority is misaligned with traditional corporate norms and what needs to change. The mismatch between capability and visibility in how cyber professionals are evaluated and excluded. A linguistic and philosophical reframe that emphasizes collaborative understanding over performative inclusion. Why many security professionals are forced to protect their organizations from internal dysfunction while defending against external threats. Trust, mission, and why so many veterans find a natural home in cyber until corporate incentives erode that foundation. Subscribe & Follow: Follow Audience 1st wherever you get your podcasts Connect with Dani Woolf on LinkedIn Learn more about CyberSynapse and qualitative buyer research This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  11. A Deep Dive Into The Multi-Cloud Mess & How AlgoSec Connects the Dots from Audience 1st, opens in a new tab

    May 9, 202541 min

    What does it really take to secure applications across a hybrid, multi-cloud environment? In this episode of Audience 1st, I sit down with Adolfo Lopez, Sales Engineer at AlgoSec, who brings a practitioner’s lens to the cloud security conversation. From his experience as a network engineer to helping organizations operationalize cloud security today, Adolfo walks us through what most teams overlook—and how to get it right. We cover: Why visibility into application flows is foundational for multi-cloud security What enterprises miss when they treat the cloud like a lift-and-shift extension of on-prem Why security must be application-centric—not infrastructure-led The critical role of policy discovery, orchestration, and automation How AlgoSec ACE helps teams answer the question: “What will break if I make this change?” If your team is working across AWS, Azure, GCP, and on-prem—and struggling to manage risk, connectivity, and policy alignment, this episode breaks it down practically and tactically. To get a demo of AlgoSec, visit: https://www.algosec.com/lp/request-a-demo This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  12. Successful Cybersecurity Marketing with Qualitative Buyer Data and Brain Power from Audience 1st, opens in a new tab

    May 2, 202544 min

    In this provocative and no-fluff episode of Keyboard Samurai, host, Wil Kluv, sits down with Dani Woolf and Ben Siegel to unpack what’s broken in how cybersecurity vendors go to market and how to fix it using real buyer data and a deeper understanding of human psychology. Dani and Ben, co-founders of CyberSynapse and veterans of cybersecurity GTM, break down why so many tech marketers are stuck in echo chambers, how pressure from investors leads to safe (but disconnected) strategies, and why most teams are making decisions without actual buyer validation. They explore the psychological barriers to change, why the “herd mentality” is sabotaging innovation, and how to replace opinion with evidence through first-party qualitative research. They also take on the traditional analyst model, offering sharp critique and a more human, scalable alternative rooted in community-sourced insight. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  13. Know Before You Go: The Empathy Codified Playbook for RSA Conference 2025 from Audience 1st, opens in a new tab

    Apr 25, 202559 min

    Most vendors won’t admit this, but we will: Your brand doesn’t have a messaging problem. It has a presence problem. And it’s why buyers leave RSA feeling numb, unseen, and unready to trust you. In this episode, Dani Woolf sits down with Zachary Hyde, someone she doesn’t always agree with, which makes this conversation one of the most honest and urgent before a major conference. Together, they break down why most GTM teams think they’re being empathetic but are actually performing a buyer-first fantasy while still clinging to control. If you're showing up to RSA Conference this year with a booth, a badge, and a team under pressure to "drive pipeline" - this is your mirror. Listen before you land in SFO. What We Cover: Why vendors fail to empathize with buyers at conferences How canned “empathetic marketing” actually erodes trust Why emotional presence is a muscle to be consistently massaged The difference between tone-matching and real psychological safety Red flags buyers spot immediately and won’t tell you about What to do this week to actually build trust at RSA (no fluff, no fake discovery) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  14. What Cybersecurity Leaders Must Learn from OT Practitioners in Underserved Critical Infrastructure from Audience 1st, opens in a new tab

    Apr 18, 202535 min

    In this episode of Audience 1st Podcast, Dani sits down with Kristin Demoranville, CEO of Anzen Sage and host of the Bites & Bytes podcast, to uncover the hidden vulnerabilities in one of the world’s most overlooked critical infrastructure sectors: food and agriculture. From insider threats in peanut processing to cyber attacks that disrupt egg supply chains, Kristin breaks down why OT security in food systems isn’t just about uptime, it’s about human lives, brand trust, and national resilience. She pulls no punches, sharing raw stories from the frontlines: Why cybersecurity leaders in food facilities are flying blind What happened when nobody spoke up at Boar’s Head How misinformation campaigns are now a cyber risk vector Why “brown cows make chocolate milk” isn’t just a joke—it’s a symptom of a dangerous knowledge gap We also unpack: The behavioral blind spots holding back executive buy-in Why empathy, not just engineering, is the key to securing food systems What must change in the next 5 years to avoid preventable tragedies This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  15. Why Most Tech “Communities” Fail Before They Begin from Audience 1st, opens in a new tab

    Apr 11, 202530 min

    Everyone in tech is suddenly “building community.” But most aren’t building anything close to the real thing - community that's built on mission, trust, and transparency. In this raw, no-buzzword conversation recorded live at CyberMarketingCon, Dani Woolf sits with Ben Siegel, George Kamide, Bronwen Hudson, and Elliot Volkman, real community builders, to unpack what community actually means, why most efforts fall flat, and what it takes to build something alive, resilient, and trustworthy - especially in an industry like cybersecurity where trust is scarce and attention is fractured. We go deep on: Why most corporate “communities” are poorly disguised funnels The difference between an audience, a user group, and a true community What trust looks like when your members are CISOs, not consumers Why growth is nonlinear, unpredictable, and absolutely not guaranteed The emotional labor and invisible moderation that holds real communities together You’ll also hear tactical advice on how to build thriving spaces across Reddit, Slack, LinkedIn, and beyond - without flashy tools or six-figure budgets. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  16. 5 Mindset Shifts Security Teams Must Adopt to Master Multi-Cloud Security from Audience 1st, opens in a new tab

    Apr 4, 202530 min

    Multi-cloud security isn’t just a technology challenge—it’s an organizational mindset problem. Security teams are juggling AWS, Azure, and GCP, each with different security models, policies, and rules. The result? Silos, misconfigurations, and security gaps big enough to drive an exploit through. In this episode, I sat down with Gal Yosef from AlgoSec to break down: Why multi-cloud security is so complex (and what security teams are getting wrong) How to bridge the gap between network security and cloud security teams How large enterprises manage cloud security policy enforcement across business units The shift from one-size-fits-all security policies to flexible, risk-based guardrails Why automation and visibility are critical for securing multi-cloud environments If you want to secure application connectivity across your hybrid environment, visit algosec.com . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  17. How to Diagnose Your Organization’s Real Growth Problem from Audience 1st, opens in a new tab

    Mar 31, 202541 min

    In this episode of Audience 1st, Dani Woolf cuts straight through the noise to confront the silent killer of growth in B2B organizations: misdiagnosing the real growth problem. Most GTM teams think they’re aligned. They’re not. Most believe they’re solving the right thing. They aren’t. In this raw, unfiltered solo episode, Dani unpacks why internal alignment is often a lie, how companies waste entire quarters solving surface-level symptoms, and what it takes to actually identify the bleeding neck - the one problem that’s quietly draining your growth, budget, and team morale. If you’ve ever felt like your team is moving fast but going nowhere, this is the episode you didn’t know you needed. What You’ll Learn: Why most organizations aren’t solving their biggest growth problem and how to tell if you’re one of them The high cost of chasing lagging indicators instead of root causes The real reason marketing, sales, and product don’t align and why buyer truth is the only fix How to recognize “growth triggers” that signal it’s time to do qualitative buyer research Dani’s four-step clarity framework: Diagnose → Validate → Align → Act How to stop guessing, and finally build from buyer reality—not internal theory Don’t just walk away from this episode inspired. Take action. Ask yourself: What’s the one growth problem we think we’re solving right now? Who told us that? When was the last time we heard it from a buyer’s mouth verbatim? What would it feel like to know we’re solving the right thing? If you’re ready to stop guessing and start listening, reach out to Dani and her team . Let’s uncover the bleeding neck together. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  18. The CISO POV Checklist That Drives Buying Decisions from Audience 1st, opens in a new tab

    Mar 31, 202541 min

    In this episode of Audience 1st Podcast, Dani Woolf sits down with Jason Loomis, Chief Information Security Officer at Freshworks, to uncover the raw truth behind how CISOs evaluate security vendors, what actually moves a deal forward, and why most POVs fall flat before they even start. Jason gets brutally honest about the emotional dynamics of enterprise buying, the real reason vendors lose trust, and what it actually takes to turn a POV into a purchase. If you’re in product marketing, sales, or demand generation at a cybersecurity company, this episode will change how you think about the buyer journey and give you a blueprint to win trust, increase conversions, and build long-term influence with technical buyers. What You’ll Learn in This Episode: Why emotional certainty - not ROI - is the key to winning a CISO’s trust The most common POV mistakes vendors make (and how to avoid them) How Jason evaluates vendors - and what gets them instantly disqualified The danger of relying on generic “What problems are you solving?” questions Why transparency beats feature-stuffing in every sales motion How to make your booth presence less awkward and more effective The impact of new SEC regulations on security budgeting and priorities Why buyers referring your product - even after saying no - is the ultimate win If you’re serious about understanding what really drives buyer decisions in cybersecurity subscribe to Audience 1st Podcast. New episodes every week. Raw, unfiltered, and straight from the source - your buyers. 🎧 Listen now, take notes, and share with your GTM team. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  19. Why the Legacy Analyst Model is Misaligned with Cybersecurity Buyer and Vendor Needs from Audience 1st, opens in a new tab

    Mar 14, 202531 min

    In this episode of Risk & Real, host Jeffrey Wheatman sits down with Dani Woolf, co-founder of CyberSynapse and CEO of Audience 1st, to discuss a major shift happening in the cybersecurity industry: the decline of the traditional analyst model and the rise of direct buyer engagement. Cybersecurity vendors that engage directly with their buyers gain faster, more actionable insights than those relying solely on traditional analyst firms. Tune in as we discuss: The flaws in the traditional analyst model and why it’s no longer aligned with today’s fast-moving cybersecurity landscape. Why analyst reports take too long to produce and how they filter buyer insights. The power of direct buyer engagement and how vendors can gather real-time, unfiltered insights. Why cybersecurity vendors are cutting back on analyst firm budgets and shifting to a hybrid research model. How CyberSynapse enables vendors to talk directly to security practitioners, CISOs, and IT leaders. Resources & Links: Learn more about CyberSynapse: https://www.cybersynapse.io Follow Dani Woolf on LinkedIn: https://www.linkedin.com/in/daniwoolf Check out Audience 1st Podcast: https://audience1st.fm Subscribe & Stay Connected! Follow Risk & Real on Apple Podcasts, Spotify, or your favorite podcast app. Connect with host Jeffrey Wheatman on LinkedIn: https://www.linkedin.com/in/jeffreywheatman Don’t forget to leave a review if you enjoyed the episode! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

  20. Why Cloud Security Starts with Applications & How to Protect Them at Scale from Audience 1st, opens in a new tab

    Mar 7, 202527 min

    Cloud security didn’t make life easier—it made it exponentially harder. Security teams are stuck in legacy network security models while trying to secure cloud-native applications, security groups, IAM policies, and ephemeral workloads. The result? Confusion, misalignment, and a security posture that can’t keep up with cloud speed. In this episode of Audience 1st Podcast, I chatted with Kyle Wickert from AlgoSec about: Why network security teams struggle with cloud security models The hidden complexity of securing applications across multi-cloud environments Why firewalls and network segmentation don’t translate well to the cloud How security teams can gain visibility and control over cloud security policies The role of automation in bridging the gap between network security and cloud security If you want to secure application connectivity across your hybrid environment, visit algosec.com . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit audience1st.substack.com

Ranking source

Apple Podcasts rankings via the Mato Topic Intelligence Platform.

Observed September 20, 2026.

Apple and Apple Podcasts are trademarks of Apple Inc., registered in the U.S. and other countries.

Pairs with

What to do with a chart

01ShowsThe shows Mato publishesEvery public Mato show, its episodes, and the Apple placements it holds.02AI talentPick the voice before the formatThe live roster of hosts, each with samples you can listen to before you commit.03How it worksFrom an idea to a published episodeWhat Mato does between the brief and the feed, step by step.

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