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As someone who works in the enterprise space, I fully agree with you. In every enterprise I've ever worked at, the purchasing process is a nightmare - it invar

As someone who works in the enterprise space, I fully agree with you. In every enterprise I've ever worked at, the purchasing process is a nightmare - it invariably takes months at best to purchase anything, and the bureaucracy, meetings and wasted time will cost you your soul. When you add up all the wasted man-hours it takes to purchase a $100 app, it will easily run to an order of magnitude more - at best. Once you've been through the purchasing grinder once, you will do just about anything to avoid purchasing anything every again. So no dammit, the vendors don't need to change - the bureaucracy-ladel, rule-ridden, time-wasting purchasing departments need to!

alangibson 6y ago
I agree with you in principle, but they're not going to reform because reform is in they eye of the beholder. For them everything is fine. They don't care how many gray hairs it costs you. Given that, it seems to me wise to look for ways to make purchasing less nightmarish without needing to reform several thousand large bureaucracies.
- GordonS 6y ago
  Even in the "happy path" where vendors accept POs, 30-day credit terms etc, the purchasing process is still a nightmare, even if it's less so than for card payments. And it's not "just" about stressing out those that interact with the purchasing process - big organisations waste a lot of otherwise productive hours, affecting their bottom line. When I consider the vast sums of money wasted by the purchasing bureaucracy where I work, it boggles the mind. Everyone knows it, but inertia and fear of change are rampant in large organisations.
pembrook 6y ago
This is why any smart Saas company is charging, at minimum, thousands of dollars per month for medium-large sized customers. They know the purchasing process will be the same headache regardless of whether the product costs $100/month or $10,000/month. If the company is large and the tool enables collaboration and time-saving, $10,000 is literally a rounding error for a company with 500+ employees in comparison to the potential value delivered. When I see B2B Saas companies with pricing plans that top out at $50/month, I want to pull my hair out. They are leaving so much money at the table and simultaneously starving themselves of the revenue needed to grow and build a long-term business.
- alangibson 6y ago
  So true. I wouldn't even try to sell an enterprise to-do app for less than 2000/month. The headaches of selling are baked in no matter what you are building.
- GordonS 6y ago
  I agree. Incredibly though, the same organisations will spend hundreds of man-hours quibbling over whether a dev team really needs a $20 app. Sometimes I really hate working for large companies!
  - dvtrn 6y ago
    I’ve come to the realization as a leader that I just do not have the skin for budget discussions of any form or variety beyond negotiating with potential hires what they would like to be paid. And what you just said about $20 apps is 100% why. I think it’s probably if not the entire reason, then part of a factor of having less power and influence in the former (Though being expected to be answerable in full for “why did cost x go up?”), and measurably more in the latter-personal history has born this out with a predictable consistency. Ask me to do the math, I will happily and eagerly get to work. Ask me to sit on a budget call and deal with the politics of who gets how many beans and I want to throw myself out a top floor window.
  - pembrook 6y ago
    Me: "John wants to use this $20 app" Manager: "Ok, schedule a meeting with the 3 of us and my boss to determine if it makes sense" Me: "The 4 of us talking about this for a half hour will cost the company $375." Manager: "..." [cut to inside the $375 meeting] Manager's Manager: "Things are tight, we just don't have the budget this year."
    - GordonS 6y ago
      In reality that would only be the first of several meetings. It might be funny if it wasn't true. I recall a couple of years back I was trying to purchase a POEditor subscription, which is $14/m. This was for a large dev project where the customer was paying us around $10M. After several meetings encompassing a ridiculous number of people, many of whom weren't related to the project in any way, I added up the costs and showed the PM: it was well into 5 figures, not accounting for loss of productive time for our customer. The PM just shrugged, "that's the way it works, they won't change".
eli 6y ago
Unfortunately legal concerns about data privacy are pushing enterprises towards MORE of this stuff, not less.
- scruple 6y ago
  Absolutely. And it is strictly security theater. We're delusional to think that checking the boxes on these arbitrary lists is making us "more secure." It's very frustrating to have a role in this game and find yourself completely unable to combat the bureaucracy.
  - slake 6y ago
    This is so true. And big corporations push around smaller vendors to have so many compliances, insurance and other certifications in place, whereas larger vendors can get away with insane security and privacy lapses just because of legacy. Makes me mad.
npsimons 6y ago
Honestly, as someone also currently inside a v. large bureaucracy, I concur. Sometimes it almost feels as if half of the "value" or "work" in selling to big businesses that I hear of is in navigating the purchasing departments. Once you've done that, you're golden. It's like picking the lock on a safe.

alangibson 6y ago

I agree with you in principle, but they're not going to reform because reform is in they eye of the beholder. For them everything is fine. They don't care how many gray hairs it costs you. Given that, it seems to me wise to look for ways to make purchasing less nightmarish without needing to reform several thousand large bureaucracies.

GordonS 6y ago
Even in the "happy path" where vendors accept POs, 30-day credit terms etc, the purchasing process is still a nightmare, even if it's less so than for card payments. And it's not "just" about stressing out those that interact with the purchasing process - big organisations waste a lot of otherwise productive hours, affecting their bottom line. When I consider the vast sums of money wasted by the purchasing bureaucracy where I work, it boggles the mind. Everyone knows it, but inertia and fear of change are rampant in large organisations.

pembrook 6y ago

This is why any smart Saas company is charging, at minimum, thousands of dollars per month for medium-large sized customers. They know the purchasing process will be the same headache regardless of whether the product costs $100/month or $10,000/month. If the company is large and the tool enables collaboration and time-saving, $10,000 is literally a rounding error for a company with 500+ employees in comparison to the potential value delivered. When I see B2B Saas companies with pricing plans that top out at $50/month, I want to pull my hair out. They are leaving so much money at the table and simultaneously starving themselves of the revenue needed to grow and build a long-term business.

alangibson 6y ago
So true. I wouldn't even try to sell an enterprise to-do app for less than 2000/month. The headaches of selling are baked in no matter what you are building.
GordonS 6y ago
I agree. Incredibly though, the same organisations will spend hundreds of man-hours quibbling over whether a dev team really needs a $20 app. Sometimes I really hate working for large companies!
- dvtrn 6y ago
  I’ve come to the realization as a leader that I just do not have the skin for budget discussions of any form or variety beyond negotiating with potential hires what they would like to be paid. And what you just said about $20 apps is 100% why. I think it’s probably if not the entire reason, then part of a factor of having less power and influence in the former (Though being expected to be answerable in full for “why did cost x go up?”), and measurably more in the latter-personal history has born this out with a predictable consistency. Ask me to do the math, I will happily and eagerly get to work. Ask me to sit on a budget call and deal with the politics of who gets how many beans and I want to throw myself out a top floor window.
- pembrook 6y ago
  Me: "John wants to use this $20 app" Manager: "Ok, schedule a meeting with the 3 of us and my boss to determine if it makes sense" Me: "The 4 of us talking about this for a half hour will cost the company $375." Manager: "..." [cut to inside the $375 meeting] Manager's Manager: "Things are tight, we just don't have the budget this year."
  - GordonS 6y ago
    In reality that would only be the first of several meetings. It might be funny if it wasn't true. I recall a couple of years back I was trying to purchase a POEditor subscription, which is $14/m. This was for a large dev project where the customer was paying us around $10M. After several meetings encompassing a ridiculous number of people, many of whom weren't related to the project in any way, I added up the costs and showed the PM: it was well into 5 figures, not accounting for loss of productive time for our customer. The PM just shrugged, "that's the way it works, they won't change".

eli 6y ago

Unfortunately legal concerns about data privacy are pushing enterprises towards MORE of this stuff, not less.

scruple 6y ago
Absolutely. And it is strictly security theater. We're delusional to think that checking the boxes on these arbitrary lists is making us "more secure." It's very frustrating to have a role in this game and find yourself completely unable to combat the bureaucracy.
- slake 6y ago
  This is so true. And big corporations push around smaller vendors to have so many compliances, insurance and other certifications in place, whereas larger vendors can get away with insane security and privacy lapses just because of legacy. Makes me mad.

npsimons 6y ago

Honestly, as someone also currently inside a v. large bureaucracy, I concur. Sometimes it almost feels as if half of the "value" or "work" in selling to big businesses that I hear of is in navigating the purchasing departments. Once you've done that, you're golden. It's like picking the lock on a safe.