How much does your company spend on software per employee per month?

Worked it out for us and it came to about 180 dollars a head once you count everything, including the tools two people use and nobody can cancel.

Curious where that sits. I have no idea if we are careful or if we are being taken for a ride.

What is yours?

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u/Sad-Instruction8890 — 2 days ago

What software do you pay for out of your own pocket because your company refused to buy it?

Someone here mentioned last month that half their real workflow runs on tools their company has never heard of. What did not come up is who is actually paying for those tools.

Nine dollars a month for a note app because the approved one is unusable. A personal Notion because the company wiki is a graveyard. A password manager because IT never got round to it.

What is on your card that should be on theirs, and how long have you been quietly covering it?

reddit.com
u/Sad-Instruction8890 — 6 days ago

Software red flags I now spot instantly (learned the hard way)

After enough bad purchases, you start noticing patterns. Sharing mine, add yours below.

🚩 "Contact us for pricing" with zero public numbers anywhere

🚩 The demo is beautiful but the free trial looks nothing like it

🚩 Onboarding call feels more like a sales pitch than actual setup help

🚩 Support response time only becomes an issue after you've already paid annually

None of these mean a tool is automatically bad, but if I see two or more together now, I slow way down before signing anything.

What's your instant red flag? The thing that makes you go "yeah, I'm not buying this" before even finishing the demo.

reddit.com
u/Sad-Instruction8890 — 15 days ago

Dear Excel, it's not you, it's me (a breakup letter to my old spreadsheet)

Dear Excel,

We had a good run. Years of tabs, at least one file named "FINAL_v3_ACTUALFINAL_useThisOne.xlsx." You gave me VLOOKUP, pivot tables, and way too many merged cell headaches.

But I met someone new. A proper database. It doesn't crash when I paste 50,000 rows or ask "keep this formatting?" seventeen times a day.

This isn't goodbye forever, you'll still handle my quick napkin math. But we both know this relationship had run its course.

Sincerely,
A guy who finally set up Postgres

reddit.com
u/Sad-Instruction8890 — 15 days ago

We switched CRMs 3 times in 2 years. Still not sure we picked right.

Just realized we're on our third CRM since I started here. Every time it's the same story, we get excited about the switch, spend weeks migrating data, and then six months later someone says "wait why did we leave the old one again?"

Quick rundown of what happened:

  1. First CRM – too basic, outgrew it in a year
  2. Second CRM – powerful but nobody actually used half the features, felt like overkill
  3. Third CRM (current) – decent so far but pricing jumped after the first year and now we're annoyed again

Each switch cost us time, money, and a chunk of sanity re-training the team. And honestly I don't think we did a bad job picking, it just feels like needs change faster than the tools do.

Anyone else stuck in this loop? How do you actually know a CRM will still make sense for your team a year or two down the line, or is some trial and error just unavoidable?

reddit.com
u/Sad-Instruction8890 — 16 days ago

Why do software reviews all sound the same? "Great tool, easy to use, highly recommend" tells me nothing

Every time I try to research a new tool before buying, I end up scrolling through pages of reviews that are basically copy-pasted vibes. "Great tool, easy to use, would recommend." Cool, but what does that actually mean for my use case?

I want to know stuff like: did it break under heavy use, was support actually helpful when something went wrong, did pricing quietly change after a year, that kind of real detail.

How do you all actually filter through the noise? Is there a way to find reviews that go deeper than a star rating and a one liner, or is asking real people in subs like this just the only reliable method left?

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u/Sad-Instruction8890 — 16 days ago

We're paying for 4 tools nobody even uses

Finance asked me to review our software spend this quarter. Took me the whole afternoon and honestly kind of annoyed me once I saw the results.

Found these just sitting there:

  1. A project management tool – team switched away 3 months ago, nobody cancelled it
  2. A design tool seat – assigned to someone who left the company 6 months ago
  3. An email marketing tool – using like 10% of it, could've been on the free plan
  4. A "wellness" app – no idea who even signed up for this one

Nobody decided to waste money, it just quietly happened over time.

Anyone else done this and found stuff you completely forgot you were paying for?

reddit.com
u/Sad-Instruction8890 — 16 days ago

How many tools does your team actually use to ship one project? I counted mine and I'm scared.

Ok so this randomly happened to me today. Client asked for a status update on a video project we're doing, and I went to pull it together and realized I had to log into like 5 different things just to answer one email.

So I actually sat down and traced the whole thing from start to finish. For ONE video project, here's what we touch:

  1. Slack – this is where the client actually talks to us day to day
  2. Notion – brief and notes live here but half the team forgets to update it
  3. Trello – supposed to be our task board, but somehow tasks still get missed
  4. Google Drive – raw footage and assets, always running out of storage
  5. Premiere Pro – actual editing obviously
  6. Frame.io – client review and feedback on cuts
  7. Zoom – calls when Slack messages get too long to type
  8. Gmail – for "official" stuff like invoices or contracts
  9. QuickBooks – so someone can actually get paid
  10. Calendly – booking calls because nobody just picks a time anymore

That's already 10 tools and I probably forgot one or two honestly. And it's not even that big of a project, it's literally editing and delivering ONE video.

The annoying part is half the miscommunication we get isn't even about the actual work, it's just stuff getting lost between apps. Like someone approves something in Slack but it never gets updated in Trello, so we redo it anyway.

u/Sad-Instruction8890 — 17 days ago

nyone else feel like review site costs jumped since G2 bought Capterra, GetApp and Software Advice?

Maybe it's just me but the leverage feels completely one-sided now. Four of the main platforms are under one roof, so there's not much pressure keeping listing and lead prices honest anymore. Trying to figure out where to actually put budget this year. Are people still paying for the big platforms, moving to smaller independent ones, or just cutting the spend and leaning on other channels? Curious what's actually working for people right now.

reddit.com
u/Sad-Instruction8890 — 21 days ago

With G2 now owning Capterra, GetApp and Software Advice, has anyone else noticed listing/lead costs creeping up?

Genuine question for other founders. Now that four of the main review platforms are under one owner, the pricing leverage has shifted hard toward the platform. Curious whether people are seeing higher costs, and where you're putting your listing budget instead. Independent options, niche directories, or just eating the G2 price?

reddit.com
u/Sad-Instruction8890 — 21 days ago

What's the best money you've ever spent on software, and what's the worst?

The one you love to dunk on, the punchline in every team chat, the tool everyone agrees is bloated and annoying. And yet if it disappeared tomorrow you'd be in real trouble. What is it?

reddit.com
u/Sad-Instruction8890 — 21 days ago

With G2 now owning Capterra, GetApp and Software Advice, has anyone else noticed listing/lead costs creeping up?

Genuine question for other founders. Now that four of the main review platforms are under one owner, the pricing leverage has shifted hard toward the platform. Curious whether people are seeing higher costs, and where you're putting your listing budget instead. Independent options, niche directories, or just eating the G2 price?

reddit.com
u/Sad-Instruction8890 — 21 days ago

There are two kinds of software people: those who read the docs and those who click around until it works. Which are you and does it depend on the tool?

Some people will not touch a new tool until they've read the manual. Others open it and start pressing things until something happens. Neither is wrong but people are weirdly loyal to their camp. Which one are you, and has a specific piece of software ever forced you to switch sides?

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u/Sad-Instruction8890 — 21 days ago

Three questions worth asking before you buy any software, learned the expensive way.

One, who else has to open this file or use this tool, because compatibility beats features the moment it leaves your desk. Two, is the price a subscription or a one time cost, because cheap monthly quietly outspends a licence in two years. Three, does it fit how you already work, or does it expect you to change how you work to suit it. What would you add to this list?

reddit.com
u/Sad-Instruction8890 — 22 days ago

After answering a few hundred "what should I buy" questions, the people who regret their purchase almost always skipped the same step.

They compared features and they compared price. What they didn't do was ask whether the tool fits how their team actually works day to day. That's the one that comes back to bite. What's the software decision you'd make differently now, and what would you check first?

reddit.com
u/Sad-Instruction8890 — 23 days ago

Spent an hour building something in a free tool today, then hit the paywall right at the export button.

Felt less like a free trial and more like a hostage situation. What's the tool that let you do all the work and then charged you to leave with it?

reddit.com
u/Sad-Instruction8890 — 24 days ago

A notification popped up during a screen share today and the whole call went quiet for a second.

Nothing wild, just enough that someone changed the subject fast. What's the most awkward thing software has ever surfaced on you at exactly the wrong moment?

reddit.com
u/Sad-Instruction8890 — 28 days ago

Shoutout to whoever built the "undo send" feature into email. You've saved me more than once.

Not a recommendation post. Just want to hear the small features, not whole products, that quietly saved you from an embarrassing mistake. What's yours?

reddit.com
u/Sad-Instruction8890 — 28 days ago