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

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 stress2. 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 one4. Why CISOs and vCISOs should be tag-teaming, not competing5. How to measure progress beyond compliance and build a culture of strategic leadership6. 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

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 

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   

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

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.

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)  

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

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.

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.

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.

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.

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.ioFollow Dani Woolf on LinkedIn: https://www.linkedin.com/in/daniwoolfCheck 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! 

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're want to secure application connectivity across your hybrid environment, visit algosec.com.

What happens when you meet a cybersecurity founder over dinner and 12 hours later, they’re on your podcast?You get one of the most brutally honest conversations about mobile security.In this episode, Rocky Cole, co-founder of iVerify, lays out why mobile security is dangerously behind—and why businesses are in denial about the scale of the threat.We dive into: The biggest myth in mobile security—why MDM (Mobile Device Management) is not a security tool and never was. Why enterprise security leaders are still ignoring mobile security (even when businesses are now prime targets). How attackers have outpaced traditional mobile security measures—and what needs to change. The operational bottlenecks holding CISOs back from fixing the problem—and how to work around them. Rocky shares raw insights from the frontlines of mobile security, including how his team uncovered new Pegasus infections, why BYOD security is broken, and what companies should be doing NOW.If you're still treating mobile devices differently than desktops, this episode will change your perspective—fast.

Welcome to the first episode of The Confident Cyber Marketer, a monthly series hosted by CyberSynapse.io! In this special in-person episode from New York City, I'm joined by Ben Siegel to break down how cybersecurity marketers and sales teams can accelerate speed to buyer insights to gain a competitive edge. In this tactical, no-BS conversation, we reveal why traditional analyst models fail, why most cybersecurity vendors get it wrong, and how real-time insights from buyers—not just customers—can drive better messaging, faster sales cycles, and higher conversion rates. Key Takeaways and Topics Covered: Why cybersecurity marketing is broken—and how to fix it The myth of proprietary data in cybersecurity marketing Why most data doesn’t tell you the full buyer story The Rapid Buyer Insight Loop (RBIL) framework for gathering and applying insights in less than two weeks The difference between customer research vs. buyer research—and why both matter How traditional analyst models hold cybersecurity vendors back Real-world stories from Dani & Ben on how shifting to direct buyer insights changed everything How to operationalize fast, actionable insights across marketing, sales, and product Metrics that matter: Time to Insight, Time to Decision, Time to Value The high cost of getting your target audience wrong—and how to avoid it. Resources & Links: 🔗 CyberSynapse – Ready to ditch the traditional analyst model and get real insights from real key decision-makers? Visit CyberSynapse.io to schedule a quick call.🔗 Connect with Dani & Ben – Let’s keep the conversation going! Find us on LinkedIn: Dani Woolf Ben Siegel Don’t forget to subscribe, share, and leave a review if you found this episode valuable. More deep dives into cybersecurity marketing that actually works coming soon!

In this episode of Audience 1st, I'm joined by Rob Shavell, co-founder of DeleteMe, to explore the data privacy space and the growing importance of human-centric security.Rob will share his journey from Silicon Valley venture capitalist to privacy entrepreneur and how being a contrarian led him to build one of the leading services in the data removal space.We'll dive into: Why privacy is no longer just a noun but an active set of actions. How AI and automation have transformed cybercrime into a “creative industry” and what it means for security teams. Why it’s difficult to quantify the impact of continuous data removal and how security leaders can build a better ROI story. How to overcome employee skepticism and drive adoption of security tools through simplicity and clear communication. We will also discusses the future of privacy, emerging threats like AI-generated deepfakes, and what security practitioners need to do to protect their people in an increasingly hostile digital world.

Early in my career as a tech marketer, I was told that securing a top-right position in an analyst report was the way to gain credibility. It didn’t take long before I started questioning the whole system. In this episode of Audience 1st, I sat down with Chase Cunningham, VP of Security Market Research at G2 and Co-Founder of Demo-Force, to dig into a hot topic: The flaws in the legacy analyst model and what a modern, buyer-centric approach to market intelligence looks like. We explored how the legacy analyst firms operate, the influence of vendor dollars on rankings, and why many CMOs are quietly walking away from the old system. Chase shared eye-opening insights into how buyers actually evaluate security solutions—hint: they’re relying more on peer reviews and real-world data than on Magic Quadrants. Key takeaways from this episode: Why vendors are overpaying for analyst influence instead of listening to buyers. How data-driven insights from G2 are reshaping go-to-market strategies. The most overlooked buyer signals that vendors should start paying attention to. The shift from C-suite-targeted sales to winning over the “lieutenants” who make buying decisions. The real truth about security software pricing, discounts, and contract lengths. If you're in cybersecurity marketing, product, or sales and looking for smarter ways to understand and reach your buyers, this episode is a must-listen. Get free access to more than 100 million people researching, comparing, and buying software on G2 every year: https://sell.g2.com/

The way cybersecurity and IT software is sold today is fundamentally broken. In this episode of Audience 1st, Chase Cunningham pulls no punches as we dive into why the traditional software demo and sales model is riddled with friction, killing deals, and frustrating buyers. We unpack the biggest flaws in go-to-market strategies, including: Why buyers expect seamless, self-service access to software—and how vendors are failing them. How manual, high-friction demos slow down sales cycles and lose deals. Why vendor fear of transparency is outdated—and actually hurting revenue. How behavioral data and automation can transform demo-to-close rates. Chase shares eye-opening stats on demo conversion rates, real-world examples of deals lost due to friction, and practical strategies for automating and optimizing the buyer experience. If you're in marketing, sales, or product and tired of watching your pipeline stall due to outdated sales motions, this episode is a must-listen. Learn how to ditch the friction, close more deals, and give buyers what they actually want here: https://www.demo-force.com/

The challenge is clear: BISOs must bridge the widening gap between security priorities and business demands, often dealing with a space that is fraught with competing interests and high stakes. But how do BISOs balance the demands of risk mitigation with the realities of operational goals? How can they make meaningful connections with vendors who often fail to understand the nuances of their role? These are the questions that Rob Dalzell, a Business Information Security Officer (BISO) at a major financial institution, grapples with regularly. In this episode of Audience 1st, I had a candid conversation with Rob, where we unearthed invaluable insights into what drives buying decisions and operational realities for BISOs.