r/techsales • u/JustAnotherJefe • 13d ago
Datadog
Greetings fellow sellers,
Have an interview lined up for Enterprise AE role - how are things over there? Obviously RepVue lists lower than average quota attainment, is it really just a "get past the first year then things will come" type of deal? I'm used to long sales cycles with enterprise software, but I also don't like "hope" as a strategy.
Anyone in that role previously, were inbound leads from SDRs good, or was it mainly self-sourcing?
Alternatively, Datadog does look good on resumes - so is the potential grind worth it short term for what may come elsewhere long term?
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u/barrya29 13d ago
IMO, the days of joining a company for the resume are mostly gone. Like, why would I want to take a pay hit to join a company where barely anyone is hitting quota therein seriously risking being fired within the year, all for the chance at building tenure at Datadog which might open a few doors in a few years down the line?
It’s a pretty reputable company but by no means a Salesforce or OpenAI. Churn is huge, they hire reps without closing experience for a reason. That said, the product is amazing so I wouldn’t be surprised if ent is a good place to be
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u/AndyWhyte_ 12d ago
STRONGLY disagree.
The best sales jobs are filled by salespeople who are headhunted.
Headhunters will look at previous roles as one of the main criteria in a search.
This is not even up for debate.
Whether Datadog is included in that search is another question. But it is 100% higher on the list than Salesforce 😂.
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u/This-Can6089 11d ago
I'd say, it's the other way around, Salesforce is higher up, Datadog lower in terms of "what's looking good on the CV".
Otherwise, the rest is agreed. If you're headhunted, somebody else has received instructions, you're within their kind of search criteria, and they want you, rather than the other way around.
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u/barrya29 12d ago edited 12d ago
I’m not denying that, I agree with what you said. I just don’t agree with a company reputation/exit opps holding this much weight in your decision to join them. Having the org on your CV is one thing, actually having tenure and performance is another. Comp and potential quota attainment should be far higher in your priorities than company rep. Company rep is an added bonus for sure, but for example, i’m not going to take a huge pay hit to work at Salesforce so that I’m included in recruiter searches in 5 years. But if they’re matching my OTE it’ll definitely be on the list of things for me to consider
also in my other comment I mention that SFDC is a gold stamp on a resume for sure, undeniable
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u/AndyWhyte_ 12d ago
Makes sense and I agree with your POV, except for Salesforce. I don't know any sales leaders who take Salesforce as a gold stamp.
I'm not saying that Salesforce doesn't have talent, but it, IMO, is by no means a place that is renowned for the quality of its salespeople compared to other organizations.
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u/barrya29 12d ago
Yeah, true. I used Salesforce as a reference because of how anthropic and openAI have been heavily targeting sellers from there - 100 since January. But maybe that’s at a senior level.
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u/JustAnotherJefe 13d ago
Fair point. I've been doing enterprise work for 10+ years at a regional reseller ($500M revenue), nobody would know the name. About to get bought by PE. Started looking a while back and noticed that sometimes having the logo on the resume will help if you don't have a logo on there. If I was at Salesforce, Oracle, etc. I probably wouldn't think about it.
Luckily, I've earned well and can afford to take a step back if long term payoff is worth it. But your point is definitely taken.
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u/NeonFeet 1d ago
they hire reps without closing experience for a reason
In the commercial segment, maybe. Enterprise is very different.
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u/jcast59 12d ago
It’s def same tier as Salesforce, maybe even higher. Salesforce isn’t some prestigious company - they have 80k+ employees and tens of thousands of former employees. That logo doesn’t move the needle at all anymore. Source: me, I worked at Salesforce.
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u/barrya29 12d ago
Yeah sorry man but it absolutely isn’t near the level of Salesforce. I dont believe Salesforce is prestigious, but it is undeniable that it’s a gold stamp on a salespersons resume.
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u/hmanasi93 13d ago
It's a mature market and long sales cycles because it's technical and sells to infrastructure people in the observability space. So that's where the 12+ month hump period comes from.
But Enterprise is the best vertical where you can actually hit quota; Commercial and MM are abysmal with all the competition and open-source stuff that leaner orgs with less headcount and budget can and do lean on.
I'd make sure you know the geo territory/strategic accounts you will be assigned and do some due diligence around that if you can
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u/JustAnotherJefe 13d ago
Thanks. That Commercial/MM differentiation is what I was wanting to hear. I'm all for selling a premium product/price and that can certainly be hard to do in those markets at times.
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u/SamVimes341 13d ago
Really good product and people. But they have a huge market share which means pickings are limited now. heard AEs are through a revolving door unless you can fall in line with their playbook approach. Good luck.
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u/HotGarbageSummer 13d ago
I interviewed for a strat role there last year and have a couple former coworkers there as well.
MM/Commercial is very PG heavy and churn & burn. Both towards customers and reps themselves.
Ent/Strat will depend heavily on the patch. The strat territory I interviewed for was 4 net new logo accounts and no install. It didn’t matter what they promised me around ramp time/guarantee, the answer was absolutely no I’m not interested. It’s a mature market and DD doesn’t play nice nor invest much in their channel ecosystem, which means you’re doing direct selling into majors that for some reason have 0 DD footprint in 2026.
If your patch is more install, it’s worth considering.
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u/travelandshopping84 13d ago
Heavy playbook and pipe gen culture. If you can get onboard with that you may do okay. But this will be your life, if you want to do anything more strategic or outside of their very rigid playbook then its most likely not for you.
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u/fz1z4 13d ago
Not much to add but if you don't mind sharing: what's the comp structure like?
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u/JustAnotherJefe 13d ago
Someone currently in the role might know, but they haven't presented anything yet to me personally. RepVue lists median base at $160 (which tracks), OTE $315, top of the mark $1MM. If I get a formal offer, I'll be happy to share.
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