Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth

On this episode of Cyber GTM Talk, the cybersecurity podcast for go-to-market leaders, Marty Overman makes the case that problem experts win in cybersecurity sales, and explains why so many reps fall back on pitching the product instead. Marty runs Americas sales at Darktrace and has been in tech sales since 2005, at Cisco, McAfee, Palo Alto Networks and Imperva. She shares what a problem-expert rep sounds like on a call, what to say when a buyer asks "what do you guys even do?", and the interview question she uses to spot sellers who will learn the buyer's world. In this episode Why sellers default to the product pitch, and how buyers box you in with "you tell us what you do and we'll decide if it fits" What to say when a buyer asks "what do you guys even do?" What a problem-expert rep sounds like with a senior security leader, and the torn-ACL test for whether the pain is worth paying to fix Why you need to understand the buyer's Cisco, Palo Alto and SentinelOne stack, not just your own product Why "I can't help you, but I know someone who can" earns more trust in cyber sales than bending your product to fit A lesson for cyber startup sales teams: why Marty pushed a startup to package its product around one problem, and why Darktrace went from many products to one platform The onboarding question Marty asks candidates to spot future problem experts Her early-detection message for Breast Cancer Awareness Month, and the leadership lesson from her own diagnosis About the guest Marty Overman is EVP of Americas Sales at Darktrace and a cyber sales leader with more than 20 years in tech sales. She spent nearly ten years at Cisco and five at McAfee, where she was named 2017 Worldwide Sales Director of the Year, then held sales leadership roles at Palo Alto Networks, Imperva, Elisity and Entersekt. Notable quotes "They go, well, just tell me about your product. What do you guys even do? And then we answer with our product instead of answering with the, here's what we do. And that's your chance to talk about that problem you solve." "They know the technology. It's thinking about the unique applications of it that we've got to help them get to." "I hear you. I understand you, and I can't help you. I would love to be able to help you, but I can't." Chapters 00:00 Intro 02:26 Why aren't more sellers problem experts? 05:47 When buyers say "just tell me what you do" 07:53 What a problem-expert rep sounds like 11:59 "That's right" beats "you're right" 14:58 Why AI security feels like cloud all over again 17:47 Opening Darktrace Live with questions, not slides 20:00 From many products to one platform 23:33 How to become a problem expert: curiosity 27:16 Saying "I can't help you" 28:38 Hiring for curiosity 30:41 Breast Cancer Awareness Month and early detection 33:12 What helped at work during treatment Cyber GTM Talk is for sales and marketing leaders at cybersecurity companies who want to grow sales, from start up sales to scale. 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.

On this episode of Cyber GTM Talk, the cybersecurity podcast for go-to-market leaders, IT-Harvest founder Richard Stiennon explains why this is a rare opening for cyber startup sales: CISOs are questioning their legacy vendors harder than he has seen in 25 years of tracking the industry. Boards are telling CISOs to deploy AI, guardrails are getting bought first, and startups with 20 customers are competing with incumbents that have thousands. He also has blunt advice for any cyber sales leader at an AI security startup who has been told to double pipeline: stop validating and make some noise.In this episodeWhy CISOs are rethinking what they already own at a level Richard has never seenBoards and CEOs telling CISOs to deploy AI, something he'd never heard of a board doing for securityWhy guardrails are the first AI security purchase, and why they're really DLP for a new channelHow a startup with 20 customers can compete with an incumbent that has thousands, and why the startup gets the easier pitchSecurity for AI vs. AI for security, and why "AI for security" is about to leave his AI security countHis advice to an AI security startup asked to double pipeline in two quarters: stop interviewing CISOs, move faster, make some noiseWhy this year's acquisitions aren't consolidation, and what that means for cyber sales teams on both sides of the dealAbout the guestRichard Stiennon is the founder and chief research analyst at IT-Harvest, which tracks every vendor and product in the cybersecurity industry. He sold the first Check Point firewall to Ford, was a Gartner security analyst and Fortinet's CMO, and wrote Guardians of the Machine Age on AI security.Notable quotes"I've never seen the level of reflection on what we already have and whether or not we should replace it.""I've never heard of boards saying to the CISOs, do security, or do more security, or double your budget. But all of a sudden we're there.""The demand is already there. So you have to tap into it. And the only way to do that is to make some noise."Chapters00:00 Intro04:03 Breaking down 567 AI security companies07:14 Why guardrails came first10:22 Guardrails are DLP for a new channel12:28 AI for security: vulnerability management, email and the SOC20:53 Boards telling CISOs to deploy AI32:49 Big vendors vs. AI-native speed38:51 Where enterprises are spending, and why legacy tools are under review47:08 Why it isn't consolidation53:27 Cyber Donut hot seat: double pipeline in two quarters58:18 What's next for IT-HarvestCyber GTM Talk helps cybersecurity sales and marketing leaders grow sales, from start up sales to scale. 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.

James Irving, cybersecurity sales leader and founder of Emotive JLI, shares why he built ThreatSpike’s sales team from graduates rather than seasoned sellers. They explore hiring for attitude, honesty and business curiosity, interviews that expose authenticity, teaching cyber through familiar analogies, surviving a disastrous sales month, and why a simple spreadsheet can outperform a complex CRM.

Ken Powell, founder of Sales Method and veteran enterprise cybersecurity sales leader, tackles the toughest competitor in cyber sales: doing nothing. He explores qualification before pitching, uncovering root causes behind stated needs, building credible payback cases, mapping executive priorities, and using disciplined account planning. The conversation also covers differentiation, forecasting, buyer risk, and when walking away strengthens credibility.

Fred Descloux, Nu Skin’s Global Director of Privacy, Data Security and GRC and founder of Zero Drama Security, has worked across selling, advising, operating, and buying cybersecurity. He explores why prepared, honest reps beat polished products, how buyers use AI for research, and why five meaningful meetings outperform twenty rushed ones. Plus: fake familiarity, peer-to-peer selling, and the real value of likability.

Kristen Twining, SVP of Sales at Reco and a veteran cybersecurity sales leader, is rebuilding go-to-market for the age of AI agents. She explores why agentic GTM must unite sales, marketing, and RevOps, the foundational data and CRM work involved, and how signal scoring reshapes outbound. They also discuss the rise of GTM engineers, AI-focused hiring, and authentic leadership.

Lauren Lynch, a cybersecurity sales executive who has scaled teams at Rapid7, Snyk, Wiz, and Drata, shares how Wiz grew from 40 to 80 people in just months. She explores structured hiring, testing coachability, validating leadership candidates, spotting AI-generated work, and keeping teams aligned through major playbook changes. She also discusses hybrid learning, AI-powered call analysis, and building resilient, high-integrity sales cultures.

Robbie Tyrie, a cybersecurity leader and fractional CISO with 26 years of experience, reveals why he repeatedly chose startups over giants like CrowdStrike. He discusses making vendor risk measurable, structuring managed trials, and using open-source tools as a safety net. He also explores why trade shows are losing buyers, how human relationships win deals, AI governance, and keeping one major customer from controlling a startup’s roadmap.

David Gee, former CIO at Eli Lilly and CISO at HSBC Asia Pacific, now advises startups and writes about technology leadership. He explains why CISOs enforce one-in, one-out buying, how AI is reshaping security budgets, and why sellers must engage 12–15 months before plans are funded. He also explores trust, CIO-CISO tensions, CFO alignment, and the pitch that won a meeting in hours.

Zach Lewis runs IT and security at a university on a tight budget, and when he needs a problem fixed, he goes looking in the startup community. He's been a sub-10 customer at Concentric AI, a very early customer at Island, a design partner for Jazz DLP, and he ran an email security product from a barely-out-of-stealth startup for four years. He explains what he gets for buying early, what he needs to see before he'll take the bet, and why your LinkedIn message almost certainly isn't how you'll reach him.In this episodeWhy a four-year run with a sub-10 email security startup turned Zach into a repeat startup buyerThe trade he makes for being early: lower pricing locked in for three or five years, and features built in weeksWhat he watches during a design partnership: the whole problem solved, the team growing, the product moving fastHow his DSPM vendor ended up working like a remote member of his teamWhy nobody inside the university pushed back on buying from startups10 to 20 LinkedIn pitches a day, three replies in seven years, one purchase, and where he finds new vendors insteadHow a deal actually gets funded in a July-to-June budget, and why something usually gets switched off firstWhy two out of three startups he sees are pitching shadow AI, and why he covered it with tools he already hadAbout the guestZach Lewis is CIO and CISO at the University of Health Sciences and Pharmacy in St. Louis, a Venture Advisor at Glilot Capital Partners, and the author of Locked Up (Wiley, 2026), the story of his university's response to a LockBit ransomware attack. He was named Non-Profit CISO of the Year in 2023.Notable quotes"I've done a 5-year on a couple startups just because we want to lock in that low pricing.""Best email security product I've ever seen.""I don't think anyone even really knew they were a startup, nor did they care."Chapters00:00 Intro03:18 Advising at Glilot and the St. Louis "cyber mafia"07:23 What he listens for in a first startup conversation09:31 How a design partnership really works13:37 Why legacy DLP failed and what Jazz does differently16:41 His first startup bet: email security20:00 Price, multi-year lock-ins, and features in weeks21:00 How much time early-stage vendors actually take23:38 Does anyone push back on buying from startups?24:38 Sorting out AI security without adding tools28:04 "Stop messaging me on LinkedIn," and what works instead33:28 How deals close: budget cycles, sunsetting, the CFO39:09 Buying after a breach41:00 Locked Up43:31 Visionary or smoking crack 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.