Pros: A good company to work for.

Cons: No demerits as such. No issues.

Pros: We are shipping features. We are paying down technical debt. We are becoming a real AI leader in Customer Service. The site is stable. Sales & Success seem better run.

Cons: Work-life balance is not what it was. The CEO talks about AI too much. We keep buying companies overseas, leading to more early mornings, more late nights, and more integration.

Pros: The office in SFO is very nice.

Cons: Zendesk has become a cautionary tale in what happens when private equity takes over a once-proud tech company. Since the buyout, the firm has gutted its leadership—firing the founder, replacing the board, and driving out many of the visionaries who actually built the business. What’s followed has been nothing short of a slow-motion collapse: five rounds of layoffs, a relentless push to offshore talent to cut costs, and a culture hollowed out by short-term financial engineering. It’s hard to overstate how far the company has fallen. What used to be a product-led, customer-obsessed organization is now steered by lawyers and finance operators whose primary concern is dressing the company up for a profitable exit—not building for the long term. The AI push is the most embarrassing part of the story. Nearly three years into this so-called transformation, Zendesk has almost nothing to show for it. Marketing slides abound, but the product impact is negligible, and customers know it. Internally, teams are burned out, priorities shift constantly, and morale is in the gutter. There’s no vision—just vague promises and cost-cutting directives from people who don’t understand the product or the space. It’s genuinely painful to watch. Zendesk once stood for empathy, for elegant design, for helping companies deliver great support. Now it’s a spreadsheet exercise run by people who treat employees as headcount rows and customers as churn risk. The talk of growth is smoke and mirrors—beneath the surface, there’s real fear about the lack of progress and the dwindling chances of an IPO. For those of us who once believed in what Zendesk could be, it’s become an embarrassing place to be associated with.