In this episode, I sit down with Ben Sizemore, Chief Information Officer at Land Gorilla, to talk about how technology buyers evaluate vendors, what makes salespeople credible with executives, and why most software pitches fail before they ever become real conversations. Ben shares why CIOs do not want to be “sold,” why cold outreach rarely works on him unless there is already some relationship or in-person context, and why the best sales conversations are grounded in facts, numbers, workflow impact, and ROI.
We also talk about what really drives lending technology purchases: operational efficiency, doing more with less, and reducing cost or manual work. Ben explains why some products become table stakes instead of delivering real ROI, how sellers should tailor their message to different executive audiences, and why he sometimes has to help vendors reshape their own pitch so they can win internal approval.
TOPICS WE COVER
Why CIOs ignore most cold outreach unless there is already context or a relationship
How conferences help vendors get in front of executives more effectively than generic emails
Why lending technology purchases usually come down to operational efficiency and ROI
What makes a software salesperson credible early: facts, numbers, preparation, and intelligent answers
Why executives do not want to be sold — they want a real conversation about workflow, value, and fit
How sellers lose deals by failing to tailor the message to the buyer, audience, and approval process
ABOUT THE GUEST
Ben Sizemore is the Chief Information Officer at Land Gorilla, a construction lending software company serving the mortgage industry and other industries where construction lending is involved. Ben has spent more than 35 years in technology and lending, and brings a CIO’s perspective on software buying, internal selling, vendor evaluation, and what executives need to hear before approving new technology.
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