The Buyer's Seat: Inside the Mind of CISOs and CIOs Buying in the Age of AI

Aysha is a technology executive with over 25 years in cybersecurity, most recently serving as CISO and CIO at Treasure Data. Known for her "spiritual CISO" persona, she blends deep operational experience with a monk-like clarity — cutting through vendor noise with equal parts wisdom and candor. In this episode, we explore the frustrations behind her Buyer's Seat series, the chronic delivery problem plaguing the cybersecurity industry, and a no-holds-barred look at how buyers actually evaluate, adopt, and renew software. Aysha shares her structured vendor evaluation process, what "fantasy math" ROI really signals, and how AI is fundamentally reshaping how she leads her team. In our in-depth discussion, Aysha shares: [00:02:45] Introducing herself as a 25-year tech executive and "spiritual CISO." [00:03:52] How being a lifelong misfit who asks too many questions shaped her leadership. [00:05:26] Why she's in the right industry to reduce noise to signal. [00:06:45] Describing her philosophy in six words. [00:07:27] What hasn't changed in 25 years: the same vendor nonsense. [00:08:14] Why she started the Inward to Outward Substack: [00:09:14] Leadership is directly proportional to inner work and knowing your own triggers. [00:11:14] The Buyer's Seat: born out of frustration with wasted time, energy, and money. [00:13:48] Why vendors don't have a buying problem — they have a delivery problem. [00:16:18] How she evaluates vendors: problem statements, success criteria, and POCs. [00:17:09] Physical "goodies" CISOs receive weekly — trophies, plants, donuts, champagne. [00:19:02] The obligation and resentment cycle gift-giving creates in buyers. [00:22:37] The 20–30 second website test every vendor must pass. [00:23:08] What actually works: warm introductions from people who have lived the problem. [00:25:33] Why operator reality is the most underrated signal in vendor recommendations. [00:28:03] A big-name vendor who went silent for 11 months and showed up with a renewal quote. [00:30:07] The SaaS AI portfolio vendor who over-promised, under-delivered, blamed custom work. [00:33:00] Why a 77% discount doesn't equal value when the product solves the wrong problem. [00:35:22] What good vendors actually do: ship, then send a clean email. No drama. [00:37:18] By the time vendors get the first call, the buyer's decision is largely already made. [00:38:02] How her fiscal year budget cycle works: problem statements defined in November. [00:44:17] Why third-party ROI reports and "fantasy math" don't influence her decisions at all. [00:46:02] Coining the term "misalignment tax" for wasted time on metrics that don't matter. [00:50:55] Login frequency, feature clicks, and training completion are not adoption. [00:54:17] What and why she actively uses tools herself. [00:57:33] Dashboards still matter in the AI era: you need to know what your agents are doing. [01:03:58] How AI has flipped information flow from a hierarchy to a circular, real-time model. [01:07:09] AI has solved her "instinct without data" problem — now both arrive simultaneously. [01:08:41] The real AI ROI: freeing her team for strategic thinking instead of tool-wrangling. [01:10:30] Why "AI ready," "AI enabled," and "AI native" are not the same thing. [01:12:50] Build vs. buy framework: build with AI or replace with AI. [01:14:16] AI is not a strategy. AI is a tool to amplify your strategy. [01:18:42] The Buyer's Seat book targeting fall of this year; sign up at thebuyerseat.com.