The $2M Meeting That Almost Failed

It was a Tuesday. We were three weeks away from signing our biggest enterprise deal ever. The contract was on the CEO's desk. Legal had approved it. And we were about to lose $2 million because nobody remembered what Dave said in a meeting four months ago.

The Setup

The deal was straightforward—or so we thought. Enterprise SaaS contract, 200 seats, three-year commitment. Standard stuff. We'd been negotiating for six months, and finally, everything was aligned.

Then their VP of Engineering mentioned, almost casually: "Oh, and just to confirm—you're still planning to support the legacy API endpoints through 2027, right? That was the dealbreaker for us back in August."

Silence. Nobody on our side knew what he was talking about.

The Panic

Our Head of Product pulled up her notes from August. Nothing. Sales checked their CRM. Nothing. I frantically searched my email. Nothing.

Meanwhile, their team was looking at us like we were idiots. Because from their perspective, we'd committed to something fundamental and then just... forgot about it.

The worst part? Our product roadmap had already deprecated those APIs. Supporting them through 2027 would cost us—conservatively—$800K in engineering time. Not supporting them would kill the deal.

The Search

We had 20 minutes before the meeting ended. I started going through everything:

• Email threads (47 of them)
• Meeting notes in Google Docs (23 documents)
• Slack messages (thousands)
• Recorded calls (thankfully we'd started recording in September)

It took 18 minutes. But I found it.

"Actually, that's interesting. We were planning to deprecate those APIs, but if it's critical for you, we could explore extending support. Let me check with engineering and get back to you."

— Dave, from our August 14th call, minute 42

Dave had said "explore extending support." The client heard "we'll extend support." Neither side followed up to clarify. For four months, we each assumed different things.

The Resolution

Armed with the actual quote, we could have a real conversation. No, we hadn't committed. But yes, we'd implied we might. We negotiated a compromise: we'd support the legacy APIs through Q2 2027 (not end of year), and they'd prioritize migrating their systems.

Deal saved. Barely.

What We Changed

That Tuesday changed everything about how we handle important discussions. Here's what we implemented:

1. Every Client Call Gets AI Summary

We use TellMeMo to automatically capture and summarize every client interaction. Not just sales calls—product discussions, support calls, everything.

2. Commitments Are Flagged

The AI identifies potential commitments and flags them for review. "We'll explore" gets tagged just like "we'll do." Because apparently, clients don't hear the difference.

3. Everything Is Searchable

Now when someone says "you promised X in August," I can search for X and find every mention across every meeting in seconds.

4. Follow-ups Are Automated

If someone says "let me get back to you," the system creates a task. No more "I thought you were handling that."

The Aftermath

Six months later, that client is our happiest customer. They love that we can instantly recall any conversation we've ever had. When they ask "what did we decide about feature Y?", we have the answer in 30 seconds.

We've closed four more enterprise deals since then. Not one has had a "wait, what did we promise?" moment. Not because we promise less—because we track better.

The Lesson

In high-stakes deals, your memory isn't good enough. Your notes aren't good enough. Your scattered documentation across email, docs, and Slack definitely isn't good enough.

You need a system that captures everything, understands context, and makes it instantly searchable. Not because you're forgetful—because $2 million mistakes happen when smart people rely on memory.