AI-First Selling Is the Future of Cybersecurity Sales - Patrick Dillon CRO @ Nudge Security

Most cyber companies bought the Claude or ChatGPT seats, handed them to every rep, and are now asking "now what?" Tal Peretz, co-founder and CEO of Onfire AI, has watched that play out across hundreds of mid-market and enterprise security vendors, and his answer is to stop pushing from the top. Start with your best rep and let the rest of the team chase him. Then take the same idea outside: skip the CISO, find the director who owns the budget, and make him the one who carries you up.In this episodeThe three tiers of AI adoption Tal sees in cyber sales teams, and why 85 to 90 percent are stuck at "we gave it to the rep"Why he starts every rollout with the A-players even though they're rarely the best AI usersThe on-site workshop where one rep's transformed week pulled his whole region along"Five by five": the agent that picks a rep's five accounts and five prospects for the week, and why each rep tweaks itWhy trust from the front line, not the tooling, makes or breaks an AI transformationOnly about 2 percent of account entries go through the CISO, so at $50M to $100M ARR the target is the directorWhy "agentic SOC" vendors pitching the CISO are talking to the wrong personHow to reach out on a signal without sounding like a creeper (and why you never mention Reddit)Tal's 2030 take: reps flip from 80 percent admin to 80 percent selling, and quotas go with itAbout the guestTal Peretz is co-founder and CEO of Onfire AI, an AI-driven GTM platform for companies selling to technical buyers. Before Onfire he was CTO at OwnID and spent nearly seven years in Israel's Unit 8200, the last two as Head of R&D.Notable quotes"Sales is a competition. Once you put the best reps first with the AI, everyone wants to fall in line.""Probably your best reps are not the best with AI yet.""If you have fifty million of ARR and you need to grow to 100 million, the CISO is not your target.""Everyone goes to the CISO. So you go to that person, and no one is connecting with him."Chapter timestamps00:04 Why an 8200 alum built for salespeople, not cyber01:55 Spin the wheel: visionary or smoking crack02:51 Three tiers of AI adoption in cyber GTM05:24 Start with your best rep, not your CRO08:15 The five by five use case11:09 Scoring your whole TAM off five years of closed-won16:39 The three barriers to agentic GTM (and the one that matters)21:16 Quality beats volume: the A/B test with people26:46 Only 2 percent get in through the CISO30:59 The SOC example: hundreds of vendors, one buyer32:40 Where the real signals live: Reddit, Discord, GitHub38:11 How to reach out on a signal without being a creeper41:34 What Onfire is building next43:41 Visionary or smoking crack: the reveal Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Mark van Oppen is 90 days into the CRO seat at SecureAuth, after four years selling a developer-led product at FusionAuth. He walks through the pre-call research he wants reps doing to connect technical pain to a business number, and why he tells them to be careful about showing it too early. He also covers his three hiring filters, what a muted seller says to a buyer, and what he's doing with the rep at 200 percent of goal who automated his own follow-up.In this episodeWhy Mark calls identity a non-optional problem, and what "critical path" changes about the saleThe step-by-step model for turning an earnings report into a cost per minute and a headcount numberWhy he tells reps not to present that model to a customer straight awayHow he runs the technical-pain-to-dollars conversation inside a one-on-one deal reviewWhy "I'm not technical" and "let me bring in my engineer" are career-limiting in this categoryThe alley-oop between AE and SE, and what twenty minutes on mute tells a buyerEnergy, excellence, experience: his three hiring filters, in that order, and why experience comes lastWhat he's doing with a rep at 200 percent of goal who built his own Claude workflowAbout the guest: Mark van Oppen is Chief Revenue Officer at SecureAuth, which he joined in 2026. He was previously VP of Sales and then CRO at FusionAuth, and before that held go-to-market roles across Blue Box, IBM, Heptio and VMware.Notable quotes"I refer to identity as a non-optional problem.""You're not going to be right, but you're going to be in the right ballpark.""It should not be the seller goes on mute and disappears for 20 minutes."Chapters (approximate)00:36 — Ninety days in, and how the SecureAuth motion differs from developer-led04:04 — Identity as a non-optional problem10:28 — The cost-per-minute homework13:24 — Coaching it inside deal reviews19:09 — Empathy for goalposts that moved23:30 — The AE and SE alley-oop25:42 — Energy, excellence, experience32:31 — The rep who automated his own follow-up38:08 — The next 90 days Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

AI made it cheap to produce content, and now every cybersecurity vendor sounds the same. Brian Reed, CMO at Corsha, argues the answer to that sameness isn't more AI, it's the human layer: real stories, congruent brand moves, and community. He gets specific on how to use AI as a story partner rather than a content mill, why your customer is the hero of every story, and how to stand out in a market of 4,000 vendors.In this episode:Why AI content creates "mass sameness," and where humans still create meaningThe golden triangle: AI as content assistant and community as the source of real storiesWhy your customer is the hero of the story, never your product, your rep, or your companyThe business-card test for a company story simple enough that every employee can tell itHow to open a sales conversation with a 30-second customer story instead of an agenda slideUsing AI to find patterns, sharpen, and retitle stories, plus building "persona" agents like his crusty OT engineerWhere the line sits between a memorable brand moment and a forgettable gimmick (Wiz vs the puppies)The three kinds of community, why "build your own" is hardest, and why community is never lead genAbout the guest: Brian Reed is CMO at Corsha, working in industrial and OT cybersecurity. His background runs from database middleware and data warehousing in the 90s through application security and the DevOps / DevSecOps movement, including helping build the All Day DevOps community, and he writes regularly on AI and storytelling.Notable quotes:"The tide raises all boats, but they're all drowning in content, and it all sounds the same.""Your product's not the hero, your sales rep isn't the hero, your company isn't the hero. The hero is the people.""Community is never, ever about lead gen. It's brand building and giving to get."Chapters (approximate):00:58 — The ugly underbelly of AI content: sameness04:41 — Who the hero of the story really is07:13 — The business-card test and "us and them"13:13 — Using AI as a story partner, and the crusty OT agent19:05 — Standing out vs gimmicks: Wiz, Island, and the puppies27:53 — The coffee truck, and de-risking bold bets33:16 — The three kinds of community37:05 — Why community is never lead gen Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Patrick Dillon, three months into the CRO seat at Nudge Security, joins Andrew to talk about what "AI-first" actually means when everyone at RSA has slapped AI on the booth. The conversation runs from product (AI-native vs. bolted-on, and the shadow AI hiding inside companies) to the go-to-market side: how he's rebuilding the team around technology, process, and people, in that order, and who he'll hire to run it.In this episode:Why companies without a deep AI strategy could be "zombie companies" that don't know it yetThe difference between AI-native, AI-first, and just connecting an LLM to your old stackHow one prospect thought they ran 2,000 apps and actually ran 5,300Why the buyers now include CFOs, compliance, and corporate counsel, not just securityFlipping "people, process, technology" to "technology, process, people" for an AI-first GTMWhy AI replaces reps who won't use AI, not salespeople as a wholeHow Patrick screens candidates for want-to, including whether they used AI to prep for the interviewWhy buyers now demand in one to three months what used to be a twelve-month roadmap promiseAbout the guest:Patrick Dillon is CRO at Nudge Security. He and Andrew first spoke on the podcast at RSA 2025, when Patrick was launching a channel program at Airlock. Nudge closed its Series A last November.Notable quotes:"You can't secure, you can't govern what you can't see.""The call is literally coming from inside your house.""It's not a skill thing or an age thing. It's really a want-to thing." Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Emily Matthews, founder and principal of NOLA Marketing, partnered with the Ponemon Institute to ask CISOs directly how vendor marketing influences their buying decisions. The resulting State of Cybersecurity Marketing Influence Report 2026 holds some surprises: webinars beat CISO dinners, hands-on workshops build the peer references buyers trust most, and the first visitor to your website is increasingly a machine.In this episode:The top two CISO complaints about cyber marketing: it differs from product reality, and it's too high-level. Emily's fix starts with coffee-walk conversations with your engineers.Why 44% of security leaders ranked webinars the most valuable event format, while peer roundtables and CISO dinners came last.Why hands-on workshops should always be free: "You should be paying them, not them paying you."How workshops become "investments in peer influence," the #1 credibility source in the research.The shift to answer engines: Bain's 80% zero-click prediction and how to make your website a better "buffet for LLMs."Emily's case study method: start with your selling points, validate them in the customer's voice, and pack the piece with reusable quotes.Why buyers rely on analysts less than they used to, and what fills the gap for the ~3,700 vendors outside the magic quadrants.Her advice for marketers coming from outside tech: keep asking why. "Fast is not an answer."About the guest: Emily Matthews is the founder and principal of NOLA Marketing. A history and English major who started in mainframe system software, she has spent her career in technical product marketing and previously worked with the Ponemon Institute on the original Cost of a Data Breach report.Notable quotes:"You should be paying them, not them paying you.""If it sounds like BS to us, it's probably going to smell bad to them too.""If you make up a case study, it sounds made up. Interview someone. Because it's real, it comes across." Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Are you struggling to capture the attention of Chief Information Security Officers (CISOs) in a saturated cybersecurity market? Join us in this enlightening episode of The Cyber Go-To-Market Talk podcast for cybersecurity sales and marketing teams, where we unpack the secrets to effective cyber security sales strategies that can elevate your approach and drive revenue growth. Host Andrew Monaghan sits down with Chris Camacho, co-founder and COO of Abstract Security, who brings a wealth of experience from his previous roles as a buyer at financial services companies. Chris shares invaluable insights into the shifting dynamics of selling cybersecurity solutions, particularly to Fortune 500 companies. He emphasizes the critical need for cyber sales teams to either reduce current spending or replace existing vendors to gain traction, making a strong first impression that resonates with decision-makers. This episode dives deep into Chris's unique journey from being a buyer of cybersecurity products to becoming a builder and seller, offering listeners a rare perspective on what works and what doesn’t in the realm of cyber security sales. With around 3,900 vendors vying for attention in the cybersecurity space, standing out is no easy feat. Chris discusses the challenges of differentiation and the evolving role of AI in both sales and product development, providing actionable insights that can help your team navigate these complexities. Building and maintaining relationships is key in the cybersecurity landscape, and Chris stresses the importance of leveraging networks effectively to understand clients' specific needs. By creating tailored solutions that demonstrate clear ROI, sales teams can not only meet but exceed client expectations. Listeners will walk away with practical takeaways on sales onboarding, sales coaching, and metrics that matter in insurance, all aimed at accelerating growth in a rapidly changing environment. This episode is packed with cybersecurity marketing insights and go to market strategies for anyone involved in cyber security sales. Whether you're part of a startup or an established company, the lessons shared here will empower you to grow sales and enhance team management capabilities. Tune in to The Cyber Go-To-Market Talk podcast for cybersecurity sales and marketing teams and discover how to navigate team challenges while building trust and scaling sales teams effectively. Don’t miss out on this opportunity to get better at marketing and drive predictable revenue growth! About the guest: Chris Camacho spent around ten years on the buy side in financial services, an early adopter of vendors like Crowdstrike and Flashpoint, before crossing over to build and sell security products. He is co-founder and COO of Abstract.Chapters:00:51 — Crossing from the buy side to the "dark side"02:55 — Why he bought CrowdStrike and Flashpoint early11:45 — A market with thousands of vendors, and the spend arms race15:33 — Three ways to fill a regional CISO event18:23 — Relationships, Ninja Jobs, and meeting his co-founder22:20 — What he interviews for (and what he doesn't)26:22 — When an AI lab lands in your category29:59 — What CISOs are telling him about AI32:22 — Reduce or replace: the way in now34:17 — AI for sellers, and his 17-year-old BDR Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Most people think revenue leadership begins after product-market fit. Rob Witmer joined Onyx Security before there was a finished product, before the company emerged from stealth, and before the market fully understood the problem they were solving.In this episode, Rob shares what revenue leadership looks like when you're employee number 11 and the first go-to-market hire. We unpack how he approached the first 30, 60, and 90 days, why experienced sales leaders can create leverage long before a company reaches its first million dollars in revenue, and how close alignment between product and go-to-market execution accelerated Onyx's growth.Rob explains how the team validated market demand for AI-agent security, how they handled customer objections when the category was still emerging, and why transparency became a competitive advantage when selling as an early-stage company. He also shares the characteristics he looks for when hiring early-stage sellers, why recruiting is one of the most important responsibilities in revenue leadership, and how speed and low-friction execution became core principles inside Onyx.The conversation also explores the realities of scaling a cybersecurity company in a rapidly changing market, the influence of Israeli startup culture on execution speed, and why outcomes matter more than features when communicating value to customers.The Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.About the guest: Rob Witmer is in his 26th year in software, roughly 20 of them as an individual contributor before moving into leadership. He was Onyx Security's first go-to-market hire, joining as employee 11 while the company was still in stealth.Notable quotes:"I was the first BDR, the first sales rep, the first operations guy, I was the first product manager.""Microsoft did more for AI agents than anyone else out there.""We want to be known as the easiest company to do business with."Chapters (approx.):00:00 — Joining Onyx as employee 1103:31 — Why early CISO reactions were humbling07:07 — How Microsoft flipped the agent market16:33 — Why hire an experienced sales leader this early22:44 — The three traits to look for28:49 — Differentiating in the noisiest market35:14 — Tim Youngblood and the people process Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Are you facing the challenge of breaking into a new vertical with no prior experience? Wondering how to accelerate credibility and revenue in unfamiliar markets? Curious about how effective networking can create exponential sales opportunities in cybersecurity? This episode tackles these questions by unpacking hands-on strategies for rapid market entry and leveraging the power of the network effect.In this conversation we discuss👉 Navigating and mapping new industry ecosystems for accelerated sales growth👉 Transforming small initial deals into major multi-account wins through strategic networking👉 Building authentic, mutually beneficial reference and networking strategies that drive brand advocacyAbout our guestJarrett Benavidez is the SVP of North America Sales at Lumu Technologies, a veteran in cyber sales since 1999. With leadership experience at Trustwave, BeyondTrust, and CloudKnox, Jarrett specializes in opening new markets and building high-impact sales teams.SummaryThe conversation focused on how a deliberate ecosystem approach, purposeful networking, and delivering real value can help sales teams break into new markets and unlock significant revenue growth. Tune in for actionable insights and proven tactics from a cybersecurity sales leader—listen now to learn how you can successfully accelerate your go-to-market efforts. Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Are your discovery calls turning into data dumps that stall deals instead of moving them forward? Frustrated by sales cycles that take forever to close, or feel like discounting is your only lever at the finish line? Looking for actionable strategies to help your team become both faster and more effective in closing cybersecurity deals? This episode brings you proven frameworks from a leader who faced (and fixed) these very challenges.In this conversation we discuss👉 Compressing lengthy sales cycles by restructuring discovery approaches👉 Motivating and aligning sales teams for aggressive growth👉 Leveraging AI and tools to enhance call coaching, follow-ups, and pipeline managementAbout our guestJohn Chiappetta is the Chief Revenue Officer (CRO) at Xona, having joined as Head of North America Sales before recently earning his promotion. With firsthand experience scaling OT at cybersecurity startups, he brings insights into transforming sales effectiveness and team performance.SummaryListen in as John shares how he shortened discovery calls for better engagement, eliminated discounting as the only closing tool, and led his sales team to significant growth. If you want to transform your cyber sales results, this episode is packed with actionable takeaways—tune in now!Connect with John on LinkedIn, learn more about Zona Systems, or book a meeting with Andrew Monaghan to accelerate your sales success. Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.

Ever feel like your cybersecurity marketing just isn’t landing with CISOs? Wondering why, despite tons of spending, cybercrime is still on the rise? Or maybe you’re looking for real ways to build trust and stand out in a crowded, AI-fueled marketplace? This episode dives straight into those questions, with honest takes and actionable ideas you can start using today.In this conversation we discuss:👉 How fast-changing tech, and especially AI, is making go-to-market harder and more complex👉 Why the cybersecurity industry keeps repeating old mistakes and what actually needs to change👉 Tips for standing out, building trust, and having real conversations with skeptical buyersAbout our guestKarl Van den Bergh is the CMO at Illumio, with previous CMO gigs at Gigamon and DataStax. He’s got a super varied background (not your standard career marketer) and brings a fresh, global perspective to tackling tough industry challenges. And he is also the 2024 Cybersecurity Marketer of the Year!SummaryYou’ll hear why Karl Van den Bergh believes “cyber is broken,” what back-to-basics marketing really looks like, and how authenticity can cut through the noise and spark real sales conversations. Give this episode a listen—you’ll walk away with new ideas you can use right away!Links & Resources:Karl Van den Bergh on LinkedInIllumio websiteBook a 30-minute chat with Andrew Monaghan Support the showThe Cyber Go-To-Market Talk is the show for cybersecurity sales leaders, founders, CROs, and go-to-market operators looking to improve cyber sales performance and build more predictable revenue growth. Hosted by Andrew Monaghan, founder of Unstoppable.do, covering cyber sales leadership, revenue leadership, sales onboarding, forecasting, pipeline generation, and cybersecurity go-to-market execution.Follow me on LinkedIn for regular posts about growing your cybersecurity startupWant to grow your revenue faster? Check out my cybersecurity sales consulting and trainingNeed ideas about how to grow your pipeline? Sign up for my newsletter.