What if the key to selling security wasn’t knowing all the answers, but challenging every assumption? For this special holiday re-air we’re revisiting one of the most talked-about episodes of Channel Security Secrets, a conversation packed with practical, unfiltered insight from Alexander Wold, Global Director of Cybersecurity at Monks. Alexander brings 16+ years of real practitioner experience to the table, but what stands out most is his philosophy: real progress comes from tenacity, curiosity, and refusing to take anything at face value. In this episode, he breaks down exactly how that mindset shapes both effective cybersecurity and effective security sales. Drawing directly from his experience as a buyer, Alexander shares what actually gets the attention of today’s cybersecurity leaders, why mass outreach falls flat, and how trusted advisors can build long-term influence by showing up where practitioners learn, conferences, local meetups, and security communities. He also explains why sellers who lead with value, relevance, and tight messaging earn far more trust than those who chase short-term wins. Takeaways: Curiosity and tenacity are differentiators, the best advisors dig deeper and never accept the first answer.Cold calls, cold emails, and AI-templated outreach fail; relevance and real value earn attention.Show up where practitioners actually gather, conferences, security meetups, community events.Solution selling beats transactional selling every time; long-term trust compounds across careers.Build value quickly: highlight impact, reduce customer effort, and keep messaging tight and thoughtful.Follow-up matters, clients live in zigzags, and timing shifts constantly.Emerging tech will reshape security, but foundational thinking still matters.Quote of the Show “How we used to secure this business is not going to be how we do it in the future. So understand that if you question how you're approaching sales today, it might make you a stronger salesperson later on in your career.” - Alexander WoldFind all episodes, show notes, and resources at: https://www.cdg.io/podcast/ Partner with us: https://www.cdg.io/partner-with-cyber-defense-group/ Links LinkedIn: https://www.linkedin.com/in/awold/ Company website: https://www.monks.com/ Book: https://www.oreilly.com/library/view/97-things-every/9781098152161/ Ways to Tune In Spotify: https://open.spotify.com/show/1gIKsOyorKMzQA7wxck4dH?si=ff617df387aa401c Apple Podcasts: https://podcasts.apple.com/us/podcast/channel-security-secrets/id1826825461 Amazon Music: https://music.amazon.com/podcasts/8703d3a3-4128-4691-8862-cb847f53f776/channel-security-secrets YouTube: https://www.youtube.com/@ChannelSecuritySecrets
