Dear Aimee: How to fund tech stack modernization when the board only wants AI

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Dear Aimee: How to fund tech stack modernization when the board only wants AI

The board won't fund infrastructure modernization, but they're demanding an AI strategy. If you're a CIO stuck in this impossible position, Aimee Cardwell shares her tactical playbook for bridging the gap and funding modernization when "not this year" is all you've heard.

From tech debt to AI budgets: bridging the gap

About Dear Aimee

Dear Aimee is an advice series for the modern technical leader. Hosted by Aimee Cardwell (CIO & CISO in Residence at Transcend) and Cameron Ivey, each episode tackles the hardest questions at the intersection of infrastructure, security, and AI, with straight talk and actionable strategies.

In this episode of Dear Aimee, CIO & CISO in Residence Aimee Cardwell tackles one of the most frustrating challenges facing technical leaders today: five years of hearing "not this year" when asking for modernization budget, only to face urgent demands for an AI strategy.

The pressure to activate AI is real. But you can't responsibly deploy AI on a foundation of legacy systems and untrustworthy data. So how do you bridge the gap? Cardwell shares the strategies that actually work, from breaking modernization into fundable chunks to making deals that unlock budget and momentum.

In this conversation, you'll learn:

Breaking it into chunks: Why asking for one large modernization budget fails, and how to reframe the work into smaller, fundable projects that build momentum and confidence.
Finding cost offsets: How to identify savings from decommissioning legacy systems, moving to cloud, or eliminating redundant licenses, even if it's only 20%, it's leverage.
Tying modernization to revenue: How to connect infrastructure work to AI projects that deliver measurable business value, creating a clear ROI for the board.
The "Split the Difference" strategy: Aimee's tactical approach to rolling out proof of concept AI projects on legacy systems while securing a commitment to fund modernization for enterprise-grade deployment.

Watch the full episode below to get the complete playbook for funding tech stack modernization in the age of AI.

Note: You can also watch this video directly on YouTube.

Submit your question

Have a tough question about infrastructure, security, or AI strategy?

Drop it in the comments on YouTube or LinkedIn, or reach out directly to Cameron or Aimee. Your question may be featured in a future episode of Dear Aimee.

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