Phil Howard & Bill Dillmeier
Bill Dillmeier
➤ Why IT presentations lose executives in 30 seconds—and the backward storytelling framework that changes everything
➤ How a CFO cut AWS costs 20% in three weeks through daily DevOps partnership sessions
➤ The Five Boss Model: Why your CFO wants to fund IT projects but can’t understand your proposals
➤ Innovation budget reality: Why 15-20% waste is expected and how to frame experimentation
➤ The Gemba Principle: Japanese leadership concept for IT-business cross-cultural integration
➤ KeyBanc benchmarking system to justify IT spend as percentage of revenue
What happens when a CFO reveals he has five different bosses?
Bill Dillmeier isn’t your typical rearview-mirror CFO. As a finance business partner with five simultaneous bosses—head of sales, head of marketing, head of product, head of engineering, and head of operations—he offers a rare insider perspective on what finance actually wants from IT leaders.
From spending three weeks reviewing AWS nightly charges with his DevOps team to defending strategic overspend to skeptical boards, Bill shares the frameworks and partnership approaches that transform IT-Finance from adversarial to strategic collaboration. He reveals why the average CTO tenure in Fortune 500/1000 companies is only 24 months, and more importantly, what IT leaders can do about it.
Bill discusses the backward storytelling framework that helps IT leaders own the room in board presentations, the Gemba principle for cross-functional integration, and why CFOs not only expect but encourage 15-20% IT budget waste on innovation and experimentation.
Navigate through key moments in this episode with timestamped highlights, from initial introductions to deep dives into real-world use cases and implementation strategies.
00:00 – Introduction and role-play: IT director meeting CFO for first time
02:04 – What keeps a CFO up at night (hint: it's not just EBITDA)
04:03 – The dream IT partnership: solving product-market fit through technology
05:19 – External help vs. internal capabilities: making the most of what you have
06:40 – Favorite department confession: sales, and why that matters for IT
09:48 – The sales-technology connection: why IT leaders should learn to sell
11:12 – Technology leaders as sales and marketing drivers through AI positioning
14:36 – The lonely top: 93% of C-level sees IT as help desk, not strategic partner
18:11 – Communication gaps: sports metaphors vs. technical jargon
20:59 – Zero trust certification example: technical achievement, executive indifference
22:37 – Gemba principle: go to where the work happens (shadow sales, host Python classes)
27:05 – AWS cost containment story: three-week deep dive, 20% reduction
29:26 – Innovation and acceptable failure: 15-20% waste is healthy and expected
31:08 – Marketing effectiveness: 2 out of 10 vs. 8 out of 10 (perception gap)
33:09 – ICP and account-based marketing: where IT leaders can drive sales effectiveness
38:40 – AI tools for sales enablement and personality research
39:20 – The 24-month CTO tenure problem: pressure to deliver vs. modernization timelines
42:30 – The hero trap: fixing everything doesn't guarantee tenure
44:55 – De-risking framework: finance partnership to stay within spend parameters
46:23 – Modernization team sport: Deloitte + internal team, day-two planning critical
51:16 – KeyBanc Capital Markets benchmarking: IT spend as percentage of revenue
52:35 – The Department of No problem: why it happens and how to fix it
54:30 – Tech debt vs. new features: the 50/50 balance that satisfies customers and cleans up
56:30 – Strategic overspend defense: dual dev teams for on-prem and cloud markets
58:30 – The backward storytelling framework: start with Q3 outcomes, then explain how 01:
02:09 – Bill's special offer: first 10 people on LinkedIn get 30 minutes free consulting
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