The Pitch #177 Aleoop: Show Me The Sales!
18 snips
Feb 11, 2026 
Meet Jesse Middleton, an investor and recovering CRO who grills go-to-market plans, and Meghan Scanlon, CEO of Aleoop and former enterprise sales leader who turned a lost deal into an AI that mines sales feedback for product signals. They demo Aleoop ingesting Gong, Slack, Jira and CRM data. Conversation covers labeling, integrations, pilot traction, pricing strategy, conversion risks, roadmap priorities, and early fundraising.
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Embed Into Existing Workflows
- Integrate Alleyoop as middleware that reads field data then writes prioritized issues back into customers' Jira/Asana to fit existing workflows.
- Do embed insights where teams already work to increase adoption and action.
Early Pilots Across Industries
- By the pitch, Alleyoop had run pilots with five Series B/C customers across crypto analytics, HR tech, and legal software.
- All pilots were unpaid and three were disqualified while three were onboarding toward paid conversion.
Start With Seat Pricing, Then Expand
- Meghan set ACV at $15,000 ($50/user/month, 25-user minimum) with plans to scale pricing as they move upmarket.
- Try starting with seat-based pricing and then expand to company-wide deals at larger customers.