Zendesk

Zendesk went private two weeks before ChatGPT launched, and the moment it came out, it was obvious that customer service would never be the same again. Shashi Upadhyay, head of product, engineering, and AI at Zendesk, joins Craig Smith to explain what the company has built since: a self-improving AI system that doesn't just resolve tickets but learns from every failure, studies what the human did to fix it, and gets measurably better over time. He calls it the resolution learning loop, and for Zendesk's best customers, it's already resolving 70 to 90% of incoming tickets autonomously, up from the 10 to 20% that chatbots managed just a few years ago. The conversation goes deep on the engineering decisions that actually matter: why hallucination is a feature, not a bug, and why the real challenge is knowing exactly when to switch from creative AI to deterministic code; why Zendesk acquired Forethought and what made their approach to going live in days rather than months so valuable; and why, despite all the momentum, Upadhyay estimates we are only about 5% through the adoption of AI in customer service. The bottleneck isn't the technology, it's the change management required to restructure how human and AI workforces operate together. His vision of the end state is striking: personal AI agents talking directly to enterprise AI agents, resolving 90% of issues instantly, while humans focus exclusively on the complex, high-value interactions that genuinely require them. Subscribe to Eye on A.I. for weekly conversations with the people building and deploying the future of AI.

Shashi Upadhyay

Head of Product, Engineering & AI

Zendesk

In this episode, Marilee Bear, SVP North America Enterprise Sales at Zendesk sits down with SaaStr's own VP of Sales, Bryan Elsesser, to talk about the best practices to deploy in motivating and organizing your sales team in Q1.

Marilee Bear

SVP North America Enterprise Sales

Zendesk

Enterprise players are not born overnight, and the march upmarket cannot come at the cost of the customers that helped get you there. Zendesk's ability to balance Enterprise customer needs with SMBs has allowed it to thrive and become one of the very few SaaS companies to exceed $1B in annual revenue. In this podcast, Adrian McDermott, Zendesk's Chief Technology Officer, will explore the importance of balance in pursuing fast, sustainable growth. Full video: https://youtu.be/XQe6KI5aebc

Adrian McDermott

Chief Technology Officer

Zendesk

As your company grows, so does the focus on enterprise deals. Learn from Zendesk senior management about how to balance your needs and organization's focus on enterprise wins to reach $1B in revenue without ever forgetting the importance of catering to your original customer base and extending those learnings into new market segments. Video and blog post: https://www.saastr.com/the-secret-sauce-to-scaling-to-1b-with-zendesk/

Sharon Prosser

VP of Global SMB GTM and Business Development

Zendesk

Astha Malik

VP of GTM Strategy, Planning and Enablement

Zendesk

Mikkel Svane is the CEO of Zendesk and author of "Startupland". Join him as he takes you through his lessons taking Zendesk beyond a billion in ARR. Mikkel founded Zendesk in Copenhagen, Denmark in 2007 before moving the company to San Francisco in 2009. Missed the session? Here's what Mikkel talks about: The future of the cloud The rise of the public cloud and re-platforming of the tech stack How business applications are sold and delivered leveraging SaaS If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin SaaStr Mikkel Svane

Mikkel Svane

CEO

Zendesk

Douglas Hanna is the GM of the Developer Platform @ Zendesk, one of the world's fastest growing SaaS startups. Before joining Zendesk, Douglas was the Founder & CEO @ Help.com where he grew the business from 1 to 16. Prior to Help, Douglas was the CEO of A Small Orange, the web hosting firm that was acquired by Endurance International Group where Douglas was on the Executive team when they went public on the NASDAQ. In Today's Episode You Will Learn: How did Douglas make his entry into the world of SaaS and Zendesk? What were the big adjustments that Douglas had to make from founding and working in smaller companies to working at Zendesk? What is the core to making the successful move? How can companies go about building a platform? What are the fundamentals to consider once you have decided on the platform approach? What are the challenges? How can a startup measure the success of their platform? What are the benchmarks and metrics that must be observed? How does testing and iteration play a role in platform success? How does Douglas approach the go to market element with regards to platforms? How has the world of platform go to market changed in the world of omni-channel? 60 Second SaaStr Biggest mistake companies make with their platform approach? Fave SaaS reading material? What does Douglas know now that he wishes he had known at the beginning? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Douglas Hanna

Douglas Hanna

GM of Developer Platform

Zendesk