Artificial Intelligence in Help Desk Automation with Pat Calhoun of Espressive
How customers experience a company’s product or service is always top of mind for executives. However, wise executives know that employee experience should be equally valued. As businesses become increasingly driven by technology, the quantity of help desk tickets are growing exponentially. Quickly solving these issues results for employees has a direct impact on employee downtime and satisfaction. Automation and artificial intelligence have emerged as a key solution to reducing mean time to response (MTTR) for help desk resolution.

In this episode, I sit with Pat Calhoun, who is Founder and CEO of Espressive. We discuss how he raised money on an idea alone, how automation is revolutionizing help desk resolution, building product for greater user adoption, developing and NLP stack, data labeling, finding your first customers, and much much more.

If your company is looking to scale it’s AI initiatives, head over to Tesoro AI ( – experts in AI strategy, staff augmentation, and AI product development.
Show Notes with Timestamps (VIDEO):
1:40 Pat’s start early start as an engineer
3:40 Pat’s first startup | Exited to Microsoft for $450 million
5:00 The genesis of Espressive | Raising money on an idea
7:50 Solving the issue in help desk resolution with automation
11:24 Improving the employee experience without requiring human intervention
15:21 Building a product that gets great user adoption
18:52 Building an NLP stack that understand the meaning AND context of a phrase
21:00 Establishing a data architecture to make accurate NLP-driven predictions
23:50 Lessons learned in the data labeling process
24:45 Determining the first few hires at Espressive
26:25 Acquiring those first few customers
27:15 “Our customers are seeing somewhere between 55%-75% reduction in tickets”
28:17 “Our first year was the year of POCs”
33:18 Did customers/CIOs care that the product was driven by AI?
34:58 Favorite Tech Tool: Kick Ass Coffee Machine – because it fuels all other innovation in company
36:12 Who inspires Pat – Bob Iger (Disney), Charles Schultz (Starbucks)


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Marc Bernstein, CEO

Previous Episode: Marc Bernstein, Co-Founder & CEO of Balto

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