- Original Poster
- #1
I've spent 15 years in B2B SaaS, starting in procurement tech, then fan experience analytics, financial services, and adtech. Across all of it, one thing never changed.
Whenever RFPs came up, everyone in the room made the same face. You know the face. The "we have to do this, but we all know how it ends" face.
A few years ago, I was working at a qualitative analytics company focused on US fan experience, college sports, and stadium NPS, tracking whether fans were happy with the warm beer and cold food served at halftime.
We got an InfoSec questionnaire from a prospective client. Standard pre-contract stuff. Except the questions were asking about technology that hadn't been relevant since the 1990s. We're talking infrastructure that predated half our team, our CTO and engineers were either in school or hadn't been born yet when some of this tech was in use.
We had to use ChatGPT to research what the questions were even asking.
Let that sink in. We were using cutting-edge AI to decode questionnaire questions about obsolete technology, just to prove we were secure enough to tell a university whether their fans preferred cold beer to warm nachos.
We got through it. But we spent two weeks on compliance theatre that had nothing to do with our actual capability or the value we were delivering. We could have spent two weeks building.
That's when it stopped being funny.
After that, I started asking around. Turns out this wasn't just my experience, it's a running joke across small businesses everywhere. You don't win RFPs unless you have a dedicated team, expensive consultants, and enterprise resources most small businesses will never have.
Same story with compliance. ISO 27001. SOC 2. GDPR. The questionnaires are deliberately complex, the consultants are deliberately expensive, and the whole system feels designed to keep small businesses out rather than bring them in.
And then there are enterprise sales methodologies: MEDDIC, SPIN, NEAT. Genuinely powerful frameworks that actually work. I've used them myself in enterprise sales conversations and seen the difference firsthand. But they're locked behind expensive training programmes that only large sales teams can justify.
Then AI arrived. I watched two reactions play out in real time. Big companies are seeing an opportunity. Small businesses and solopreneurs are seeing fear and uncertainty about what it means for their future.
That felt wrong. AI should be a tool that helps humans compete, not a force that makes them irrelevant.
I ended up building something to try and level the playing field a bit, but I'm still figuring out where the real pain is.
My current belief is that most small businesses don't even try to compete on RFPs or compliance-heavy deals; they just route around them entirely.
Curious if that matches reality for others here. Have you actually tried going after these contracts, or just written them off?
Whenever RFPs came up, everyone in the room made the same face. You know the face. The "we have to do this, but we all know how it ends" face.
A few years ago, I was working at a qualitative analytics company focused on US fan experience, college sports, and stadium NPS, tracking whether fans were happy with the warm beer and cold food served at halftime.
We got an InfoSec questionnaire from a prospective client. Standard pre-contract stuff. Except the questions were asking about technology that hadn't been relevant since the 1990s. We're talking infrastructure that predated half our team, our CTO and engineers were either in school or hadn't been born yet when some of this tech was in use.
We had to use ChatGPT to research what the questions were even asking.
Let that sink in. We were using cutting-edge AI to decode questionnaire questions about obsolete technology, just to prove we were secure enough to tell a university whether their fans preferred cold beer to warm nachos.
We got through it. But we spent two weeks on compliance theatre that had nothing to do with our actual capability or the value we were delivering. We could have spent two weeks building.
That's when it stopped being funny.
After that, I started asking around. Turns out this wasn't just my experience, it's a running joke across small businesses everywhere. You don't win RFPs unless you have a dedicated team, expensive consultants, and enterprise resources most small businesses will never have.
Same story with compliance. ISO 27001. SOC 2. GDPR. The questionnaires are deliberately complex, the consultants are deliberately expensive, and the whole system feels designed to keep small businesses out rather than bring them in.
And then there are enterprise sales methodologies: MEDDIC, SPIN, NEAT. Genuinely powerful frameworks that actually work. I've used them myself in enterprise sales conversations and seen the difference firsthand. But they're locked behind expensive training programmes that only large sales teams can justify.
Then AI arrived. I watched two reactions play out in real time. Big companies are seeing an opportunity. Small businesses and solopreneurs are seeing fear and uncertainty about what it means for their future.
That felt wrong. AI should be a tool that helps humans compete, not a force that makes them irrelevant.
I ended up building something to try and level the playing field a bit, but I'm still figuring out where the real pain is.
My current belief is that most small businesses don't even try to compete on RFPs or compliance-heavy deals; they just route around them entirely.
Curious if that matches reality for others here. Have you actually tried going after these contracts, or just written them off?
Emojis
Used As
Bullet points
