Long process. Recruiting screen, HM screen, technical screen, panel of 6 onsite interviews, and 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 userbase to up to 50 times its current size, backing it all up with figures and data and market analysis, then gave them a full implementation plan complete with org structure, prioritization, milestones, and level of effort. It consumed a whole weekend. Apparently, according to the feedback, they were turned off by coming in with a clear perspective on this and wanted me to express uncertainty and ask *them* to decide, 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.