Zendesk

The office in SFO is very nice.

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.

1. Stop Managing for the Exit, Start Managing for Value

You can’t cut your way to greatness. The obsession with margins and cost reduction might make the spreadsheets look good for a while, but it’s destroying long-term value. Shift focus from financial engineering to actual product differentiation and customer value. If you're serious about an IPO someday, you need more than optics—you need growth, innovation, and loyalty.

1. Reconnect With the Product and the Front Lines

Get closer to the teams doing the work and the customers using the platform. Right now, decision-making feels abstract and out of touch. Visit customers. Sit in on support calls. Talk to frontline engineers and product managers. Your best insight isn’t coming from consultants or finance dashboards—it’s buried in the conversations you’re not having.

1. Make AI Actually Useful, or Kill the Hype

Three years into an AI strategy and still no clear wins? That’s a failure of execution and focus. Pick real use cases, measure outcomes, and stop chasing buzzwords. If AI is just a marketing pillar without measurable customer value, it’s doing more damage than good.

1. Invest in Talent, Not Just Cheap Labor

Offshoring isn’t a strategy—it’s a tactic. And if you're cutting experienced teams and replacing them with lower-cost centers, you’re trading institutional knowledge and innovation for short-term savings. That will catch up with you—especially in a product-led business. Invest in talent wherever it exists, and reward the people building real value.

1. Repair the Culture, or Lose What’s Left

Your culture is broken. People know the company is being run by people who don’t care about the mission. You can't fake passion or alignment. If you want people to stay—and more importantly, care—you need to rebuild trust. Be honest. Own the mistakes. Bring in leadership with a point of view beyond “maximize EBITDA.”