Pros
There are few companies that maintain a mix of a great end-user product, increasing technological relevancy and real enterprise adoption. Datadog has all three and much more. There are real cross & upsell opportunities across accounts. Datadog's new products are attracting real, enterprise interest. There is a unique opportunity to not only attain high earnings but be part of a rarified group of high-growth enterprise technology companies which combines real growth and great opportunities for learning all within a hyper-relevant sector.
Cons
A relatively technical sale- great SE's and PM's are available to assist, but the breadth of technical knowledge required to sound capable with clients is significant. This is not an old-school sales motion. The pace of innovation, release of new products and PG-focused outbound model dictate that you have to be constantly working - both hard and intelligently - to keep up. Datadog is often replacing legacy incumbents, which requires a combination of startup tech evangelism and executive champion building, especially within slower-moving larger prospects.