B2B Cybersecurity Sales: Why the Startup Beats the Incumbent

Why would a security leader at a large organization pick a startup over a big player like CrowdStrike? Robbie Tyrie did it more than once, and in this episode of Cyber GTM Talk he lays out the buyer's math behind B2B cybersecurity sales to a mid-market or enterprise account: what the buyer risks, what they get back, and what the incumbent can't offer. Robbie spent 26 years in security at J.P. Morgan Asset Management, FNZ, Tesco Bank and others before becoming CTO of a pen testing startup and then founding Torridon Cyber, where he's a fractional CISO for fintech scale-ups. That makes him the buyer your reps are calling. He covers the cybersecurity sales strategies that worked on him when he was selling cybersecurity solutions internally to his own leadership: an agreed baseline, get-out clauses, and a trial short enough that nobody can argue with it. It's a cyber GTM conversation about cyber sales from the side of the table that signs. In this episode: The two answers a big vendor gives when you ask for a feature: no, or $100,000 and six months Robbie's risk math for a startup vendor: what you lose is a couple of months The cybersecurity sales pitch he wanted to hear: build the tool around my requirements Quarterly meetings with the CEO and head of development, not an account manager The managed free trial: two weeks, a month maximum, run as a mini case study Why buyers have stopped going to trade shows, and where Robbie finds them instead What JP Morgan did to Fortify's roadmap, and the roundtable fix Cyber GTM Talk is the podcast for sales, marketing and founding teams at cybersecurity companies. Subscribe for more conversations on cybersecurity sales and marketing with the people who buy and the people who sell. Keywords: cybersecurity sales, cyber sales, cyber gtm, cybersecurity marketing, cybersecurity sales techniques, cybersecurity sales training, cybersecurity sales best practices, enterprise cybersecurity solutions, cybersecurity sales funnel, cybersecurity market trends 2026, cybersecurity lead generation, cybersecurity partnerships and alliances, cybersecurity industry sales growth