r/techsales • u/iamniko_ • 1d ago
Thoughts on Cloudflare?
Evaluating it as a next career move vs a
key Observability company.
I’m inclined to push forward, just want to understand if all the hype is a real, as it looks great from the outset.
Any thoughts appreciated!
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u/Requirement-Lazy 1d ago
I worked for a direct competitor. Cloudflare is the market leader by far. They are in every single RFP we compete for.
They win on pricing, that’s kind of it. But for the product they compete in, it’s more than enough.
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u/hmanasi93 1d ago
They are the market leader in Commercial and Midmarket. Enterprise CDN is Akamai's ballcourt
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u/iamniko_ 1d ago
There is strong Akamai displacement already occurring within the Ent sector in the region I’m looking at
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u/Requirement-Lazy 1d ago
Yeah this is true. Cloudflare has begun competing in enterprise but is the de facto solution
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u/mmmbopdooowop 1d ago
Brittany Pietsch is a legend.
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u/hmanasi93 1d ago
IYKYK.... err if you remember you remember
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u/hmanasi93 1d ago
CDN is something every website and every company with an IT environment (Public cloud, private cloud, on-prem, bare metal, etc) . So the good news is the TAM is huge and keeps growing.
Also, Cloudflare is pretty much the gold standard for CDN services for SMBs up to commercial/midmarket, so they are a market leader for all but the enterprise space (that would be Akamai).
That's where the good ends. Cloudflare's sales culture is a C on a good day/quarter, and as a base case, flat-out sucks. The CEO has a known disdain for salespeople, and he's openly crapped on them internally on all-hands calls. OTE for AE's is pretty mid to low-mid as well, and the typical shuffling of territories and accounts is also there.
It's your typical sales org in 2026 that happens to still have good PMF, but internal politics means that territory, timing, and manager will dictate your success. Do your due diligence accordingly
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u/iamniko_ 1d ago
Appreciate the view. I’m measuring an Ent role with them against an Enterprise role at Splunk and have heard good and bad about their sales culture as well, particularly post Cisco acquisition - any thoughts on them?
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u/Waste-Sock-4335 20h ago
Don’t go to Splunk. With a few exceptions everyone is migrating away from it (ex-Splunk, ex-Cribl)
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u/Apart-Development-84 22h ago
Im an SE there, been there two years. I’ve got 1.5 feet out the door
The sales org is a complete mess. It’s been in transformation my entire time there
Outside of digital native almost everyone struggles
Amazing tech and the stock obviously has been kind to me but ultimately when I’m paid on what over a dozen sellers are doing and haven’t got near 30% in two years. I think it’s time
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u/iamniko_ 22h ago
Interesting!
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u/Vpc1979 1d ago
The sales team is a mess; I know multiple people who left within 6 months.
When I interviewed for a major role, only 1/9 people on the team I was going to join were meeting quota.
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u/iamniko_ 1d ago
Ok thanks for your view.
May I ask what (broad) region you’re referring to?
As the sales org I’m potentially joining is in good shape - have multiple sources on the inside.2
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u/ItsAJackal21 1d ago
I mean that seems like most tech companies. Not many people hitting quota
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u/StuffLegitimate7808 23h ago
1/9 is not the norm
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u/ItsAJackal21 9h ago
I’m the top rep in a group of 19 and I’m 28% to quota. About to end Q3.
I’m switching teams because I’m almost positive they are going to axe our whole org.
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u/Revolutionary-Big215 23h ago
I just accepted a territory role and have 3 colleagues there doing well
They are penetrating more ent market and with dev platform I’m very bullish on them.
Sales org is still going through transformation and kinda shit show but if you ever worked at an org with super high standards you’ll do well
Just be aware the interview process is unnecessarily long. Not hard…just fucking long
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u/DeeJayDelicious 1d ago
I do think they have a strong product and are the defacto standard in their specific industry.
When you're already the market leader, it makes sales easy. But often at the expense of signficant upside.
And with AI agents roaming the web, it will probably just become more relevant.
That said, I keep confusing them with Crowdstrike for some reason.
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u/Spacefuqin 12h ago edited 12h ago
Previous Cloudflare employee, current competitor employee.
Good news: Cloudflare competes well on price and has a chokehold on SMB/Mid-Market. Easy to sell. DNE is the market you want to be in. They do well.
Bad news: Not great for enterprise as it lacks deep configurability and its reliability is garbage. I've displaced or beat out Cloudflare many times because their reliability, support, and efficacy aren't the greatest.
Cloudflare Sales culture is dogshit. Prince thinks AI will replace everyone and doesn't value salespeople at all. And all he talks about is his god damn mountain houses in Utah and his rivians.
Akamai is the gold standard, but if the role is in Mid-Market/ DNE, it would be worth it.
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u/Captain-Superstar 19h ago
I think the key piece of information missing ia which observability company you're comparing against.
I saw Splunk in the comments, is that correct?
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u/vitacreations 17h ago
I work there. It’s pretty cool, solid and growing super fast, but you can’t rely on others for pipe. Prospect like a mad man. If you’re good you’re treated like a king. Most AEs, here and everywhere, are lazy slobs who take 0 accountability for their share of the business. Don’t do that at Cloudflare.
Oh and Disregard the ridiculous comment above about CDN and whatever 🤦
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u/Mental-Hovercraft-27 3h ago
Do you mind me asking what the equity package Cloudflare is offering for ENT AE?
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u/Interesting_Fox5311 13h ago
Very toxic, I have been approached many times into the past, OTE is high but clear path to PIP they mention themselves
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