Useful or Spam? A CISO's Guide to Vendor Outreach

Why do so many vendors still get it wrong when selling to security leaders? Welcome to Razorwire, the podcast where we share our take on the world of cybersecurity with direct, practical advice for professionals and business owners alike. I'm Jim and in this episode, I'm joined by Marius Poskus, CISO at a fintech organisation and host of the Cyber Diaries podcast, and Simon Woods, co-founder of One Compliance and a salesperson who's been working in cybersecurity sales for over 15 years. If you're a CISO, you already know how this goes. The same regurgitated emails, the "just 30 seconds of your time" cold calls, the pitches that lead with product features instead of understanding what problem you're actually trying to solve. It's one of the most complained about topics on LinkedIn and in this episode we sit down with a CISO who gets sold to every day and also someone who does the selling to talk about why so much of it is broken. The conversation covers why persistence without research is just spam, why the best vendor relationships take years to build, why AI-generated outreach is making things worse and what salespeople actually need to do differently if they want to get through the door. Whether you're on the receiving end of the hundredth cold approach this week or you're a vendor trying to work out why nobody's responding, there's something in this for both sides. Three key talking points: Why most sales approaches fail before they even start: Sales in cybersecurity has a low barrier to entry, and it shows. We talk why the industry seems to have settled into a cycle of lazy, templated outreach that treats every CISO the same. We cover why this isn't just annoying for the people on the receiving end but how it actively damages the reputation of vendors who might genuinely have something useful to offer. Relationships over transactions: The best vendor relationships in cybersecurity don't start with a sale. They start with genuine engagement, understanding someone's challenges and being useful before there's any commercial benefit. This episode makes the case that the salespeople who build real connections, who act as a first port of call rather than a product pusher, are the ones who eventually get through the door. What good actually looks like: So what does getting it right look like? We break down the practical habits and mindset shifts that separate the salespeople who get responses from the ones who get blocked, and why the answer has far less to do with product knowledge than most people think. If you've ever wanted to tell a salesperson exactly where they're going wrong, this episode does it for you. And if you're the salesperson, consider this a free masterclass. On what every salesperson should think about before hitting send: “Salespeople are not trying to understand the problems that CISOs face. It's all about selling features and product instead of understanding where the pain points are." Marius Poskus Listen to this episode on your favourite podcasting platform: https://razorwire.captivate.fm/listen In this episode, we covered the following topics: Why Your Inbox Is Full of Rubbish Find out why so many vendor approaches are lazy, untargeted and AI-generated, and why the low barrier to entry in cybersecurity sales means it's unlikely to improve any time soon. What Makes a Vendor Worth Your Time Discover the signs that a vendor has actually done their homework, understands your challenges and is worth a conversation, versus the ones who are just working through a list. How to Spot a Vendor Who's Out of Their Depth Learn the warning signs that someone is bluffing through a technical conversation rather than being honest about what they know and don't know, and why that should affect your procurement decisions. What You Can Tell From a Single Email Understand why the first approach from a vendor tells you almost everything you need to know about whether they're worth engaging with, and what the red flags look like. Why Vendors Keep Getting It Wrong Find out why so much sales outreach in cybersecurity follows the same broken playbook, and why understanding the mechanics behind it helps you filter faster. It's Not Just Vendors Explore why recruiters, lead generation companies and adjacent industries are all guilty of the same lazy outreach, and why CISOs are getting hit from every direction, not just product sales. When a Vendor Relationship Actually Pays Off Find out what a genuinely useful vendor relationship looks like from the buying side and how to recognise when someone is investing in you rather than just your budget. Managing the Noise So You Don't Miss What Matters Understand why the sheer volume of bad outreach creates a real risk of filtering out the vendors who could genuinely help, and how to build a process that catches the good ones without drowning in the rest. Resources Mentioned Never Split the Difference by Chris Voss One Compliance RMI Cyber Cyber Diaries podcast CTRL+ALT+DEFEND Connect with your host James Rees Hello, I am James Rees, the host of the Razorwire podcast. This podcast brings you insights from leading cyber security professionals who dedicate their careers to making a hacker’s life that much more difficult. Our guests bring you experience and expertise from a range of disciplines and from different career stages. We give you various viewpoints for improving your cyber security – from seasoned professionals with years of experience, triumphs and lessons learned under their belt, to those in relatively early stages of their careers offering fresh eyes and new insights. With new episodes every other Wednesday, Razorwire is a podcast for cyber security enthusiasts and professionals providing insights, news and fresh ideas on protecting your organisation from hackers. For more information about us or if you have any questions you would like us to discuss email [email protected]. If you need consultation, visit www.razorthorn.com, We give our clients a personalised, integrated approach to information security, driven by our belief in quality and discretion. LinkedIn: Razorthorn Security YouTube: Razorthorn Security TikTok: Razorwire Podcast Instagram: Razorwire Podcast Twitter: @RazorThornLTD Website: www.razorthorn.com All rights reserved. © Razorthorn Security LTD 2025