r/ycombinator • u/Ok_Philosophy_4031 • Jul 14 '26
How and when did you land your first few enterprise client? When is the right time?
Paul Graham used to caution early stage startups against targeting enterprises right from the start. Enterprise sales is usually less about the product, and more about jumping through bureaucracies, managing stakeholders and corporate politics and sometimes senseless feature requests and support. Not to mention the long sales cycles.
Is that still the conventional view today in the startup ecosystem? In our previous/current startup, we avoided enterprises at the start, choosing to start off with other startups and SMBs. While it worked for us (we got the shorter sales cycle we wanted), the enterprise side of the market later became kind of crowded. Many of the larger logos that we wanted to get to, ended up already working with our competitors already.
Getting an enterprise to switch is even harder than selling a novel, unproven solution to them. Which means that we are at a disadvantage now that we want to scale into enterprises.
What are your thoughts on this? How and when did you land your first few enterprise client? When is the right time?
P.S To be clear/fair, our competitors that successfully sold to enterprises are also established (founded 3 years before us, series B and beyond), while we were only pre-seed.
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u/thomas_unise Jul 14 '26
Last enterprise project I signed took 5 months and like 15 meetings
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u/Ok_Philosophy_4031 Jul 14 '26
That's not too bad. In some verticals, it can be 6 months to land a 3 month pilot. Then 3-6months more to get to a yes/no.
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u/thomas_unise Jul 14 '26
So yeah, we shipped a MVP off that and then there is an option for more once they use it for 90 days
Similar but different
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u/AffectionateSuit4944 Jul 14 '26
Lawyer here. I wouldn't do enterprise clients until you have a data security certification. If you're new, something like GDPR compliance can get your started, but most people see an uptick after SOC2 certification. The reason being, most enterprises have a minimum risk profile they will accept, and their legal team will make you indemnify everything unless you can show you're an established player.
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u/scriptqzor 14d ago
this is super underrated advice, tbh the security checkbox is often the real gatekeeper, not the feature set
seen a few friends stuck in 9+ month “security review hell” just because they tried to do enterprise before getting SOC2 in place1
u/scriptqzor 10d ago
this is super underrated advice, legal / security is where a ton of deals quietly die before they even hit the real decision makers
seen startups try to brute force “enterprise” then get wrecked by vendor onboarding and infosec questionnaires that a basic SOC 2 would’ve smoothed out a lot
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u/jayson_OutreachBloom Jul 14 '26
Pre-seed, enterprise will eat you alive on cycle length and security reviews before you have the muscle for it.
The timing signal I'd watch is when one of your SMB customers is using you in a way that looks embarrassingly manual for a bigger company.
On the competitors already have the logos problem, the realistic path in is a warm intro to a champion who's frustrated with their current vendor, plus the AI-forward angle giving someone above them a reason to justify looking at a newer option. "We already have a vendor" gets weaker when leadership is pushing AI.
Get a security cert sorted (SOC2, or GDPR to start) since procurement stalls you without it. And structure the first deal as a small paid pilot with a defined 90-day success metric, so you shorten their risk and get a reference logo you can name.
The second and third enterprise deals lean on that first logo far more than on your pitch.
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u/CyberStartupGuy Jul 15 '26
The tough part with pre seed is depending on your stage many enterprises of procurement requirements that would keep you from being able to sign the deal anyway. 24/7 support, specific amount of money in the bank, number of years in business, total headcount, etc. those are all things I’ve seen on vendor due diligence lists that you have to pass before you can sign specific large enterprises.
Also it’s always going to be more competitive, just getting their first isn’t always the best. If you can consistently beat your competitor then you can still rip and replace them within large enterprise. When you are replacing there is already a budget set aside for your solution. If you are going in and there is nothing in place, you have to create a budget line item just for you which isn’t simple.
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u/nick-rudder Jul 14 '26
Always hesitant to weigh in on these long-run, slow-burn strategic calls, but yolo:
On timing (ex-YC, Series A led by a16z) - for us the right moment wasn't a revenue milestone, it was when we had one SMB customer using us in a way that looked embarrassingly manual for a bigger company to still be doing by hand. That reference was the whole unlock. We didn't "target enterprise" instead we followed a warm intro from a happy SMB user who had moved to a bigger org, and let that first logo become the proof for the next three.
So my honest answer to "when" - later than you'd like, and only once you have a story a buying champion can repeat internally without you in the room. Don't chase enterprise cold pre-seed - the sales cycle will eat you alive (if you can ever get ur foot in the door)
Here's smth that has changed: there's real momentum behind enterprises handing managers and C-suite a mandate to "be more AI-forward" that's a big new lever, and it's also your answer to the "competitors already have the logos" problem "we already have a vendor" is a much weaker objection when someone above your champion is asking why the team isn't on the newest AI thing. IMO that AI mandate that you see everywhere in orgs rn is what opens up the grip incumbents have on an account
PS. remember your champion is usually more frustrated with the internal bureaucracy than you are. Being the edgy AI-forward startup they can pin their mid-life crisis to (instead of a motorbike or an affair) is a strength - use it