Chris Anzalone is the founder and CEO of Knowledge, an AI-driven sales intelligence startup reshaping the way businesses identify in-market buyers. With a unique background in high-ticket finance and agency sales, Chris bootstrapped Knowledge from a services-based business into a fast-scaling SaaS company, reaching thousands of users and notable ARR growth. In this episode, he shares how data, psychographic matching, and real human connection are unlocking the next frontier of outbound sales.
In Today’s Episode We Discuss:
00:01 – Intro & Background
02:00 – Wall Street to Sales Agency
04:40 – The CMO Dinner That Changed Everything
06:30 – Building the First Predictive Model
08:00 – Psychographic Matching & Neural Match
09:20 – Exiting the Agency, Entering SaaS
11:15 – Using Knowledge to Sell Knowledge
13:30 – Breaking Through with PLG
15:00 – Case Study: 26 Deals from 5,000 Emails
17:00 – Real-Time Data & Slack Alerts
20:00 – Onboarding & Personalization Engine
23:00 – Individual vs. Account-Based Intent
24:00 – Bootstrapping with Personal Capital
27:00 – Co-Founder Equity & Ownership
30:00 – ZoomInfo, Frenemies & Market Friction
33:30 – PLG Growth Inside Enterprises
34:10 – Pricing & “Guerilla Pilots”
36:00 – Broader Use Cases Beyond Sales
37:30 – AI SDRs vs. Human Connection
42:00 – Lessons from Exit #1
44:00 – Strategic Fundraising & Skipping Seed
47:30 – The Role of the Human in AI Sales
51:20 – Cold Outreach & Cobra Kai Story
52:30 – Most Underrated Sales Tactic
56:00 – Who’s Flying Blind on Buyer Intent?
58:33 – Wrap-Up
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