Does Datadog offer family leave?

Well known brand in the observability space with a robust platform of tools The opportunity to work with a group of very smart people. Especially across the Product and Sales Engineering orgs. Both groups were essential parts of the enterprise sales motion Extra benefits like the fitness reimbursement and maternity leave which pays out a percentage of commissions while on leave. They also offered fertility assistance. Catered lunch 3x a week Generous 3 quarter ramp period

Pay - leadership from the c-suite to sales have the mindset “it sells itself” which explains the below market-value salary for the expectations Enjoy the ramp/MBO bonus while it lasts because the majority of the sales org was far below quota. Enterprise, mid-market and commercial included. It wasn’t uncommon for those who do close deals to have their commissions retroactively restructured to benefit the company and keep reps around for long lock up periods…golden handcuffs. Complicated pricing that frustrates customers Some pockets of great ICs turned leaders but mostly a boys club of sycophants who were self serving and dishonest. Constantly changing goals and arbitrary KPIs that did little to increase billings but packed calendars with ineffective internal meetings to justify the bloated middle management structure. Mandatory 3-day RTO. There are not enough desks to support the current sales org so good luck fighting for desks or phone booths. Otherwise you can take calls from the cafe where they serve free lunch!

The company invests heavily in developing individual sales skills. Training sessions are held very frequently, allowing reps to continuously sharpen their discovery and communication techniques. This environment can be a good fit for younger salespeople who want to grow quickly on a personal level. There is absolutely no gender discrimination in the workplace. That said, considerations for maternity or parental leave are virtually nonexistent—even for women.

The sales culture is extremely aggressive and "macho," resembling a high-pressure sports team environment. Almost everything is outbound, with virtually no inbound leads—sales are nearly 100% direct. There’s little to no understanding of the Japanese market, and no real go-to-market (GTM) strategy exists. While individual training is strong, it's not backed by any structured sales enablement or market-tailored strategy, putting all the burden on the rep. Each rep in Japan is allowed to freely choose 100 target accounts, but in reality, everyone swarms around the same "easy win" startups—many of which already use Datadog or have been approached countless times. The account list feels like slash-and-burn farming: overworked, short-sighted, and ultimately unsustainable. This makes it a tough environment for those in their 30s or going through life stage changes.

Great company culture, good management peering, good benefits, amazing people

Complex tech stack, a lot of internal developed tools which take time to master, a lot of team site distribution, office attendance metrics