Cyber Go-To-Market Talk | Cybersecurity B2B Sales, Marketing & Revenue Growth

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.

Cyber startups churn through heads of sales, and the usual explanation is a bad hire. Matt Calligan, Director of Growth Markets at ArmorText, argues something different. Founder-led product-market fit only proves the founder can sell, and there's a stage between that and scale that most companies skip. He calls it the Vanguard stage and lays out what has to be true before anyone hands a VP of Sales a number.In this episodeWhy early cyber buyers are "buying access to the founder," not the productThe four lights that have to turn green before you scale: a defined motion, a non-founder who can sell it, proof at volume, and junior reps who can run it without churnWhy junior AEs vs. a seasoned VP is a false binary, and the personality type Matt hires for insteadWhy your President's Club rock star is often the wrong person for the first seatHow ArmorText's founder-run hour-long demo became a five-minute UI walkthroughWhat to do when your founder won't let go of the long feature demoHow the unicorn math of a VC fund pushes founders to skip the middle stageAbout the guestMatt Calligan is Director of Growth Markets at ArmorText, which builds secure out-of-band collaboration for incident response teams. He has spent two decades in enterprise sales, including co-founding Influents as VP of Sales, and has worked on ArmorText's go-to-market since 2018.Notable quotes"If your process is still requiring the founder, then what you have is a founder and an AE in a trench coat." (tightened)"This stage takes as long as it takes.""Founders are always salesperson number one."Chapters00:06 Welcome and the spin-the-wheel game01:51 Why cyber startups go through three heads of sales05:16 What product-market fit actually proves08:57 Founders are always salesperson number one11:20 Fund math and the pressure to skip steps16:11 Why cyber's chasm is inverted18:49 The four lights of the Vanguard stage21:28 Who to hire for the first seat24:48 Do it a hundred times: hearing why the baby is ugly26:32 From a 60-minute demo to five minutes30:40 How to get the founder to let go32:52 When to stop preserving runway and floor it38:47 The reverse channel program43:35 Questions to ask before joining as a founding AE45:57 Differentiation teardown 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.

Scott Johnson, founder of Amplifyed, helps cybersecurity and SaaS companies win in search. He explores how AI tools like Claude and ChatGPT are creating a surprising new sales channel, why buyer prompts reveal powerful intent, and how vendors can measure invisible influence. They also discuss data-rich testimonials, authentic expertise, competitor comparisons, and why mass-produced AI content may soon fade.

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.

Chris Camacho, co-founder and COO of Abstract Security and former buy-side cybersecurity practitioner in financial services. He discusses moving from buyer to builder, how he chose early vendors like CrowdStrike, de-risking startup picks, making one-shot impressions with Fortune 500 CISOs, standing out in a crowded market, running regional CISO events, leveraging relationships, hiring creative sellers, and practical uses of AI in security sales.

Rob Witmer, VP of Sales at Onyx Security and the company’s first go-to-market hire, joined in stealth to build revenue from scratch. He recounts meeting CISOs pre-launch, shaping product-market fit, and recruiting early sellers. Conversation covers validating demand for AI-agent security, selling transparently as an early vendor, and the playbook for fast, low-friction GTM execution.