In partnership with
Welcome back. As longtime subscribers know, Macro Talk is hyper-focused on three things: figuring out how businesses and the economy will change, what happens to jobs and the future of work, and how to play it all.
In today’s edition, Zendesk CEO Tom Eggemeier lays out his perspectives across all of these topics — something Macro Talk strives with every interview. But of the thousands of CEOs and executives I’ve sat across over my 12-year career, few have shown up the way Eggemeier and his comms team did: no notes, no pre-reviewed topics or questions, no limits on where the conversation will go, no PR person in the room, no requests to review any of the content ahead of publication. It was a very atypical experience for me with someone this senior.
So, what did I take it all to mean? Yes there was mutual trust, but there was clearly strong conviction behind the company’s strategy, and Eggemeier himself was unafraid to share his own mind his own story.
I know there were circumstances that made this dynamic possible (the fact that they’re private, for example), but I think it’s more achievable than most sources and comms groups realize. More on this in a future post.
Sign your colleagues and CEOs up here for more unfiltered insights on my process. Transparency, to me, is paramount for trust.
THE RISING TIDE:
Software Pricing Based on Outcomes
Source: a16z, December 2024
Zendesk — a roughly 5,500-employee strong, customer service software firm based in San Francisco — is eyeing $1 billion of AI ARR in 2028 up from an expected $400 million this year, CEO Tom Eggemeier tells me in a new episode of the Macro Talk podcast.
Driving that optimism and growth is a type of software pricing strategy that Zendesk has been experimenting with the last few years: charging customers for outcomes versus the number of people using a platform.
The practice has been gaining popularity, but it’s also attracted heavy debate.
“As soon as you start charging for success, the customer begins to rethink the results. Did your product really drive the outcome? Or did they drive the outcome, with a small assist from the product?” Kyle Poyar, founder and CEO of Growth Unhinged, wrote in a popular LinkedIn post in 2025.
“I suspect there will be a wave of new tools & approaches to help AI companies [measure] exactly that. But for now, you're (probably) better off charging for work delivered rather than business outcomes unlocked,” he added.
Venture heavyweights a16z reflected on this trend back in December 2024, citing underlying AI usage costs as a driver of the shift:
“Nearly every AI startup builds on foundation models (e.g., OpenAI, Anthropic, Mistral) which come with significant variable costs that scale with AI model usage.
Every API call, every token processed, adds to their cost structure. This is a fundamental change in the underlying unit economics of pricing the AI service.
The marginal cost of an additional user or usage is not zero and varies by user. And while inference costs are dropping dramatically, tasks requiring the newest models with advanced reasoning capabilities still incur relatively high costs.
AI companies are leaning into usage-based pricing to account for this.”
Companies like Zendesk are not AI-native the way new startups are. But in leaning on the technology to go faster and grow bigger, leaner, the need for a different pricing model clearly exists.
From a macro view perspective, the other interesting part of a16z’s argument was this: “Software is becoming labor.” (As an aside, I have so many thoughts on this framing.)
“Traditional services that required human labor — like customer support, sales, marketing, or back-office finance administration — can now be automated and packaged as software products. This has blurred the line between software and service pricing models.”
The authors of the a16z post, Ivan Makarov, James da Costa, Bobby Pinero, conclude that there’s no one-size-fits-all. Experimenting is key, they write. And that’s just what Zendesk and Eggemeier have been doing.
"Right now, in this AI transformation and trying to lead from the front ... it's nice to be private," he said. At the same time, Eggemeier was clear that he thinks “seats” will go away over time.
“How much time?” I asked.
Watch the full interview or download the Macro Talk podcast companion guide to find out his answer.
The guide is my way of helping you save time because I know not everyone can watch a 48-minute podcast!
Paid subscribers can access the 28-page resource — complete with a clean and fact-checked transcript and annotated with notes — for free (a $39 value) in the link below.
The New Rules of Online Visibility
Your customers are searching in places your strategy doesn’t reach.
So before your business is buried and left behind, you need to understand the new rules of SEO.
BELAY's SEO in the Age of AI report explains how search is changing, what AI means for your visibility, and the practical steps small businesses like yours can take to stay visible.
BELAY’s U.S.-based Marketing Assistants turn strategy into execution, helping your business stay visible, credible, and competitive in every search.
LEADERS TO WATCH:
TOM EGGEMEIER, CEO OF ZENDESK
In our nearly hour-long chat in San Francisco on the sidelines of HumanX in April, Eggemeier also shared how he's building with AI at home with his kids and his views on the future of work as more employees interact with and manage bots.
He also called out Anthropic and Microsoft for putting out dramatic job loss predictions in a way I haven't seen other CEOs do.
-"As a former lawyer, to think 50% of all junior or entry-level attorney positions are gonna be gone in twelve, eighteen months — I just say categorically it will not happen."
“There are legal and regulatory points. There are change points with people. There is a point where you need entry-level people to ultimately be the mid-managers and the senior leaders of different companies in the future.
And so if you have no people coming in for these entry-level jobs, you're going to have a problem in five or ten or fifteen years as a company.”
He also offered other predictions on the future of work, including what happens to office politics, whether a-hole employees will have a-hole agents, tactics like sucking up, middle management pressures, and Zoom’s bet on digital twins:
Subscribe to Macro Talk to read the rest.
Become a paying subscriber of Macro Talk to get access to this post and other subscriber-only content.
Upgrade