402- From Selling to CIOs to Becoming One w/Karl Weber

You've Been Heard

Philip Howard

Tech News, Technology, Business, Management, News

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🗓️ 5 March 2026

⏱️ 28 minutes

🔗️ Recording | iTunes | RSS

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Summary

Karl Weber spent 30 years in technology sales before becoming CIO at Rolfson Oil. His biggest insight: stop selling to the CIO and start solving the business problem. Karl Weber has a rare perspective. He spent 30 years on the vendor side selling technology, then crossed over to become CIO at Rolfson Oil, a 500-employee fuel transportation company delivering 30 million gallons monthly to oil fields. What he discovered will change how you think about IT leadership. Karl inherited a mess: four or five overlapping tools with no strategy. His sales background taught him something most CIOs miss: "I had a lot of success trying not to sell the CIO. I wanted to sell to the person that had the business problem." The budget and pain sit with business unit leaders, not IT. We get into his one-question decision filter (does this impact revenue?), why AI investments will face a reckoning in 18 months, and the Gap pitch that won a 100,000-employee deal because his team wore their clothes. The payoff? A framework for becoming the strategic advisor executives actually want at the table, not the afterthought they call when decisions are already made. Key takeaways: One decision filter: does this impact revenue or not?; Sell to the business problem owner, not the CIO; Ask 'why' before 'how' to uncover real needs

Transcript

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0:00.0	So, Carl, I'm Doug Kameen.
0:11.2	I'm one of the co-hosts of the You've Been Heard IT Leadership Podcast.
0:14.6	Welcome to the podcast.
0:16.0	And thank you for joining us this morning.
0:17.6	Sure.
0:18.0	Glad to be here.
0:19.4	So, Carl, we've got the title here, vendor sales to
0:22.4	CIO. Your background is not coming up through the IT chain. Recently, you've been in the IT
0:28.9	site. So tell us a little bit about your history and how you got to now. I've been in the
0:33.6	technology space, my whole career, but from the other side. And this probably leads to one of
0:40.0	the questions that people typically like to come around to. I thought it was sort of the bottom of
0:44.2	your list, which is tell us about your first computer, which is probably a really good starting point for
0:48.8	me is. So I went to college in the mid late 80s, even worse. And And I was in business school trying to figure out what I'm going to do.
0:57.8	I'm going to get a business degree, and then I have no clue what I'm going to do.
1:01.5	And the school of business that I was at, hold a small group of students aside and said,
1:07.7	here's a personal computer.
1:10.0	And you get to use this while you're in school.
1:14.1	And if you graduate, you get to keep it.
1:16.4	If you don't graduate, you got to give it back.
1:18.9	Now, this wasn't any computer.
1:20.3	This was a clone IBM AT with two floppy drives, no hard drive, and a green screen
1:27.0	monitor. Yeah. And it was an hard drive, and a green screen monitor.
	...

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