High Stakes Newsletter

High Stakes Newsletter

Smart takes for those selling to, buying from, or building in enterprise tech.

Featured Posts

Green AIGreen AI
+2+2
Issue #8: Vibe Code These Four B2B 'Clean AI' Ideas.

Issue #8: Vibe Code These Four B2B 'Clean AI' Ideas.

IT Services folks, these 4 ideas tick the “coolness” box as much as the “client need” box.

Srini Annamaraju
Srini Annamaraju
Issue #9 - Board, Are You Ready for AI Unknowns?

Issue #9 - Board, Are You Ready for AI Unknowns?

Just in the past ten days, the AI governance drumbeat has grown impossible to ignore.

Srini Annamaraju
Srini Annamaraju
Enterprise AIEnterprise AI
+3+3
Issue #10: Pay Bonus? To Drive AI Copilot Adoption? Sure!

Issue #10: Pay Bonus? To Drive AI Copilot Adoption? Sure!

Don't dismiss the idea! Copilot adoption incentives have been known to unlock ROI for enterprise AI.

Srini Annamaraju
Srini Annamaraju

Archive

Enterprise AIEnterprise AI
Issue #15 Ten Opportunities Hiding in the AI Security Certification Wave

Issue #15 Ten Opportunities Hiding in the AI Security Certification Wave

Monetize the AI security wave before 2026 hits.

Srini Annamaraju
Srini Annamaraju
Enterprise AIEnterprise AI
+1+1
Issue #14 Why Your AI Pipelines Need a Zero-Trust Mesh Before Something Breaks

Issue #14 Why Your AI Pipelines Need a Zero-Trust Mesh Before Something Breaks

You won’t know what broke until it’s too late unless trust is built in from the start.

Srini Annamaraju
Srini Annamaraju
Enterprise AIEnterprise AI
+1+1
Issue #13: Will Your CFO Enforce a One-Year AI Payback?

Issue #13: Will Your CFO Enforce a One-Year AI Payback?

Why CFOs are demanding one-year returns on AI pilots and how enterprise teams can pivot to secure funding.

Srini Annamaraju
Srini Annamaraju
Issue #12: Build Robust Enterprise AI Vaults

Issue #12: Build Robust Enterprise AI Vaults

GenAI fails without clean, governed data. Stonebrook shows how to fix that.

Srini Annamaraju
Srini Annamaraju
Issue #11: Are Your AI Policies Still “PDF”? Really?

Issue #11: Are Your AI Policies Still “PDF”? Really?

It’s High Time to Move to Policy-as-Code.

Srini Annamaraju
Srini Annamaraju
Enterprise AIEnterprise AI
+3+3
Issue #10: Pay Bonus? To Drive AI Copilot Adoption? Sure!

Issue #10: Pay Bonus? To Drive AI Copilot Adoption? Sure!

Don't dismiss the idea! Copilot adoption incentives have been known to unlock ROI for enterprise AI.

Srini Annamaraju
Srini Annamaraju
Issue #9 - Board, Are You Ready for AI Unknowns?

Issue #9 - Board, Are You Ready for AI Unknowns?

Just in the past ten days, the AI governance drumbeat has grown impossible to ignore.

Srini Annamaraju
Srini Annamaraju
Green AIGreen AI
+2+2
Issue #8: Vibe Code These Four B2B 'Clean AI' Ideas.

Issue #8: Vibe Code These Four B2B 'Clean AI' Ideas.

IT Services folks, these 4 ideas tick the “coolness” box as much as the “client need” box.

Srini Annamaraju
Srini Annamaraju
Issue #7: When Prompts Go Rogue, Revenue Leaks

Issue #7: When Prompts Go Rogue, Revenue Leaks

Even when users don’t write prompts in an enterprise setting, they trigger them and the risks show up in client-facing workflows.

Srini Annamaraju
Srini Annamaraju
Issue #6: AI Literacy: The New Excel

Issue #6: AI Literacy: The New Excel

High time enterprise sellers and buyers must stop treating AI fluency like a side hobby.

Srini Annamaraju
Srini Annamaraju
Issue #5: B2B SaaS Founder, Paying the Hidden AI Tax?

Issue #5: B2B SaaS Founder, Paying the Hidden AI Tax?

Smart AI features. But flat renewals, creeping infra bills, margin pressure. That feels like AI Tax. Here is how to fix.

Srini Annamaraju
Srini Annamaraju
Issue #4: AI is Changing Developer Hiring: What it Means for Sellers & Buyers

Issue #4: AI is Changing Developer Hiring: What it Means for Sellers & Buyers

How AI is Redefining Engineering Talent, GTM Strategies, and Customer Success

Srini Annamaraju
Srini Annamaraju
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