LossEnterprise SaaS
Procurement ambush in month nine. The CFO change I should have seen coming.
$2.4M ARR · 9-month cycle · 14 stakeholders
— Enterprise AE, Series C SaaS
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Deal Anatomy
Real deals,
dissected together.
Every deal is a case study in applied epistemology — what the buyer knew, what they believed, where their doubt began. Share yours. Ask about someone else’s. No highlights reel. Just honest craft, dissected together.
No judgement
A lost deal taught honestly is worth more than a won deal told for applause. Every outcome belongs here.
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Stuck mid-deal? Not sure what to do next? Post it. This is a room full of people who’ve been exactly there.
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The comment that helps one person unstick a deal helps hundreds reading silently. Share what you see.
Recent deals in the room
Members-only · ~180 breakdowns inside
WinMid-Market
Champion left two weeks before signature. How we kept the deal alive anyway.
$180K ACV · 4-month cycle · 6 stakeholders
— Senior AE, vertical SaaS
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StalledEnterprise
Five months of silence after a perfect demo. What I learned about champion depth.
$1.1M ARR · stalled Q3 · 11 stakeholders
— Strategic AE, data infra
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LossSMB
We won the pilot. We lost the expansion. Here's exactly where I took my eye off.
$95K → $0 · 11-month arc · land-expand fail
— Account Manager, horizontal SaaS
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WinEnterprise
The pricing conversation that saved a $3M deal from commoditization.
$3.2M ARR · 7-month cycle · value-based pricing
— Enterprise AE, platform company
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LossPublic Sector
The RFP I should have no-bid. A post-mortem on sunk-cost deal chasing.
$840K · 13-month cycle · lost on price
— Public Sector AE, cybersecurity
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