The interview process was long and involved:

• Recruiting screen
• Hiring Manager screen
• Technical screen
• A panel of six onsite interviews
• A presentation

Feedback was all positive throughout, but it was ultimately a colossal waste of time. I put together a proposal that could open up a new, highly scalable revenue stream for them and grow their user base up to 50 times its current size. I backed it all up with figures, data, and market analysis, then gave them a full implementation plan complete with an organizational structure, prioritization, milestones, and level of effort. It consumed a whole weekend.

Apparently, according to the feedback, they were turned off by my coming in with a clear perspective on this and wanted me to express uncertainty and ask them to decide. This is something no candidate for a leadership role would ever do in an interview, much less one that is formulated as a presentation. And this is for a Director role, not a VP, where first-principles strategizing is usually beyond the scope of the job to begin with.

I came away not just with a poor impression of the process, which demanded far more effort of me than it did of them, but a poor impression of Datadog's leadership and doubts about their desire to win in the market. If I were invested in their stock, this experience with their senior leaders in the room was so bizarre and upside down that it would have prompted me to sell.

What new product would you create for Datadog?