Caddie
SeedRaised Since FeaturedAutomate inbound, book more demos
AI-powered scheduling and lead qualification tool that removes friction from B2B demo booking.
About
Caddie (now Superbar) streamlines the B2B sales funnel by replacing manual SDR qualification with an intelligent, self-service demo booking experience. The platform personalizes the scheduling flow, qualifies inbound leads through targeted questions, routes prospects to the right Account Executive using logic and scoring, and enables qualified buyers to book demos immediately. By auto-populating contact information from a 200M+ record database, Caddie eliminates the friction that causes 83% of interested buyers to drop off before ever seeing a demo. Founded by Alan Nowogrodski (former VP Product at FreshBooks, where he grew a unit from zero to $30M+ ARR) and Marshall Johnston, the company graduated from Y Combinator S22 and is based in Toronto. The company has since pivoted to Superbar, an AI sales assistant for websites that combines search with personalized sales guidance for e-commerce.
DailyDropout Take
Caddie tackled a real pain point in B2B sales — the massive drop-off between interest and demo. By collapsing qualification and scheduling into one step, they proved the model before pivoting to Superbar, an AI sales layer for websites.
Discovery signal: YC S22 batch, strong founder background (FreshBooks growth), clear product-market fit signal with 2X demo increase
What Makes Them Unique
Combines lead qualification, routing, and scheduling into a single frictionless flow that replaces manual SDR steps, reducing pipeline drop-off by eliminating the traditional qualify-then-schedule handoff.
2X more demos
Demo Increase
50% faster lead-to-opportunity
Deal Speed
200M+ records
Contact Database
Target Markets
Founders
Alan Nowogrodski
Co-Founder & CEO
Former VP Product at FreshBooks where he grew a unit from zero to $30M+ annual revenue. Previously VP of Product Management and VP of Marketing/Engineering Operations at NinjaCat.
Caddie is hiring!
Team size: 7
Funding History
Lead: Y Combinator
Lead: Pioneer Fund