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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