Issue #2: The AI Funding Approvals Merry-Go-Round

-Hey High Stakers,-

Good morning and welcome to the 4th issue of High Stakes!

Hearing about battle skirmishes from the enterprise trenches on AI Project approvals? I have got some gossip - and a solid enterprise-grade template - to share.

If you are a Sales or Account Lead, give this to your clients and get brownie points. Or, if you are a CXO/CFO, take this away for implementation!

-But First: Why a Special Template for AI Projects?

Why single out AI projects?! Aren’t they just another Digital Transformation project?

AI projects deserve special handling not because they’re shiny, but because they’re structurally different.

• AI projects span IT, Ops, and Business. They don’t fit neatly into any single function.

• Costs are scattered. Cloud, training, licensing, and integration sit on different lines.

• Returns are vague. ROI is hard to prove until scaled—traditional models don’t hold.

• Risks are unfamiliar. Ethical, reputational, and compliance concerns are harder to assess.

• Unlike Digital, AI creates new workflows. It augments judgment, not systems—raising ambiguity and scrutiny.

The CFO has seen 100 cloud transformations. She hasn’t (yet!) seen 100 AI agents make strategic decisions.

What you’ll take away from this edition:

• Why AI projects keep dying in the finance review cycle

• How to speak CFO without dumbing down the tech

• A free, standardized approval framework for enterprise AI investments

• Real-world use cases where it’s already working

 📅 Welcome to the AI Funding Approvals Merry-Go-Round

And yes, it’s still spinning.

CFO:

"Another AI proposal lands on my desk, promising to revolutionize our business. But when I dig into the numbers, it's all buzzwords and vague promises. Where's the concrete ROI? How does this align with our strategic goals? I can't approve projects based on hype alone. Show me the real financial impact, the risks, and a clear path to implementation. Until then, it's just another shiny toy eating up our budget."

CIO:

"We're falling behind our competitors every day we don't invest in AI. This isn't just another IT project—it's the future of our industry. Yes, the financials are still being worked out, but the potential is enormous. If we wait for perfect numbers, we'll miss the boat entirely. We need to move fast, experiment, and iterate. The real cost isn't in implementing AI—it's in being left behind."

This is the vibe across boardrooms globally: tech sponsors asking for urgency, finance demanding certainty.

Neither side is wrong. They’re just solving different things.

And that disconnect is killing good ideas.

🛎️What It Looks Like In Real Life

Picture this: A data science lead walks into a budget review with a deck titled "Unlocking Enterprise Knowledge: A RAG-Based Vector Search Initiative."

By slide 3, the CFO's eyes are glazing over. By slide 6, they're doodling on a Post-it, wondering if this is just another fancy chatbot or something that will actually shift a KPI.

Meanwhile, across the org:

• The CIO’s team buries GPT-4 Turbo costs under "cloud infra" to avoid red flags.

• Marketing cites "monthly active prompts" as a KPI.

• SalesOps rebrands their rules engine as "AI-enhanced automation."

Finance? Drowning in a sea of inconsistent, jargon-heavy, hard-to-compare proposals.

None of this is malicious. It’s just messy.

Tech leaders think in possibility.

CFOs think in predictability.

⚡Why This Friction Persists (Even in 2025)

Despite increased AI maturity, approvals still hit roadblocks:

• Proposals don’t align with financial review frameworks

• Costs are split across CapEx, OpEx, and cloud line items

• ROI is tied to speculative productivity gains, not clear outcomes

• Vendor contracts and compliance reviews are out of sync

One CIO put it plainly: "It takes us longer to get AI projects approved than to pilot and deploy them."

And with GenAI expanding into every department, the volume of requests is skyrocketing.

The result: AI projects die not because they’re flawed, but because the paperwork doesn’t speak finance.

🔧So We Built a Fix

A single, standardized, finance-friendly format for AI investment approvals.

✅ Built with feedback from CFOs, CIOs, and delivery teams

✅ Aligns Legal, Risk, Procurement, and IT into one structured flow

✅ Enables Finance to compare like-for-like across proposals

✅ Lets AI champions frame initiatives in business terms

You can grab it here and make it your own:

It includes:

• Pre-submission guidance for project sponsors

• Requestor section covering business case, break-even, and strategic alignment

• Cost breakdowns by CapEx, OpEx, Cloud, and Training

• Risk and compliance fields for privacy, vendors, and scalability

• CFO validation section with IRR thresholds and ROI logic

• Final approval workflow across business, finance, legal, and IT

🚀Who Is It For?

This is a plug-and-play asset for anyone selling or managing AI in enterprise:

• Consulting firms: Send it to clients as a pre-sales value-add

• B2B SaaS vendors: Give your champion a tool to navigate internal finance

• Enterprise teams: Standardize internal justifications, accelerate CFO buy-in

• Investors: Distribute across portfolio companies to reduce friction

🔍Real World Impact (So Far)

We’ve seen this template reduce approval cycles by 30-40% in some organizations.

Finance teams report faster decision-making and fewer back-and-forth loops.

Project sponsors finally have a "language translator" between tech ambition and fiscal scrutiny.

One client said, "This changed how we pitch AI to the board. It gave us a way to show ambition without triggering risk aversion."

🔹The Playbook (TL;DR)

• In your funding requests, stop leading with model types - start with business outcomes.

• Translate tech value into financial levers: revenue, margin, risk.

• Use consistent cost breakdowns to avoid Finance redlines.

• Align stakeholders before submission (Legal, Risk, IT).

• Give CFOs what they need: clarity, comparability, and control.

Let's stop losing good projects to bad formatting.

Let's help buyers say "yes" to the right ideas—faster.

See you in the next one.

Best,
Srini

P.S. Seen something like this before? Drop your best (or worst) AI proposal story in the comments.

I’ll reply with insights—or send you the template directly.