Businesses today are confronted with a dizzying array of options when it comes to digital modernization and embracing technological innovation. Decision-making when it comes to technology investment is often slow, and the costs incurred when those investments do not work out as planned can be painfully high. Poor solution choices have resulted in failure rates of up to 75%, according to some estimates, and even those investments that do succeed often come with hefty price tags that can put a drag on revenues.
To learn what companies in the financial services space can do to make better technology choices, I caught up with Charlie Day, SVP, Sales and Advisory, at UPSTACK, at FinovateFall 2025 earlier this year. UPSTACK is a technology advisory platform that helps businesses reduce costs, accelerate deployment, and simplify IT decision-making. The company offers vendor-agnostic expertise, with recommendations powered by both AI and UPSTACK’s vendor experience, all informed by the firm’s proprietary dataset.
In this conversation, Day explains how UPSTACK combines a focus on long-term relationships, human expertise, and AI-powered insights to drive business success and help companies achieve their goals in an ever-evolving technology landscape.
Technological advisory has really shifted into more of a strategic relationship. It’s not just about a transaction, an event, or a sale, but a true, long-term relationship beyond the technology choice. We mix the technology expertise we have with marketing insights—everything from pricing to integration capabilities to how certain selections will mix into their overall IT landscape—to ensure that our customers are making not only the right decision in a short snapshot in time, but also what’s going to keep them achieving their goals over the long term.
Charlie Day brings more than 20 years of experience in enterprise sales and strategic partnerships. He has held leadership roles at 8×8, RingCentral, Oracle, and AT&T. Day has business degrees from the University of New Hampshire and Southern New Hampshire University.
UPSTACK is a vendor-neutral, full-service technology brokerage. Founded in 2017 and headquartered in New York City, the company provides expert advisory and execution services to help businesses make smarter technology decisions. UPSTACK works with companies across the entire technology landscape, including colocation, cloud, connectivity, networking, cybersecurity, AI, and more. With more than 60 customers in the Fortune 1000, UPSTACK recently acquired Breakwater Cloud Advisors, a CX consultancy specializing in contact center modernization, automation, and AI transformation. Christopher Trapp is UPSTACK’s Founder and CEO.
Photo by Sonja Langford on Unsplash
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