Outbound sales is broken—and Chris Anzalone is on a mission to fix it.
As the founder and CEO of Knowledge, Chris brings a rare combination of Wall Street capital formation expertise, high-ticket sales experience, and a deep understanding of what makes outbound work today—and what no longer does.
In a recent episode of the Ignite Podcast, Chris breaks down how he went from running a sales agency to launching a fast-scaling AI startup that’s flipping the script on intent data and targeting.
For those who don’t have time to tune in, here’s what you need to know:
From Wall Street to Sales Agency to SaaS Founder
Chris didn’t follow the typical SaaS founder path. He started in finance, raising money from family offices and hedge funds, and cut his teeth building rapport with high-stakes investors. That foundation taught him one thing: sales is about trust, timing, and connection.
After burning out from a decade in finance, he launched a go-to-market agency. But he quickly realized what most agencies and companies miss: setting meetings is easy—setting meetings that convert is hard.
The Dinner That Changed Everything
Chris attended a private dinner with CMOs from Fortune 500 companies. That night, he uncovered the pain points large enterprises face with intent data and agency partnerships. The message was clear: everyone wants qualified meetings, not activity metrics.
That insight led him to scrap his agency’s positioning overnight—and build a new data-first strategy focused on matching sales reps with buyers who are actually in-market.
Neural Match: When AI Understands Buyers Like Humans Do
Chris and his team built “Neural Match,” a machine learning model trained on:
180 million sales calls
22 billion rows of historical intent
Over 3,000 psychographic data points per contact
A trillion rows of behavior data refreshed daily
Instead of focusing on companies, Knowledge identifies individuals who are demonstrating real buyer behavior—like researching pain points or reading competitor reviews—before they reach out to a vendor.
And here’s the kicker: the system matches prospects not just on intent, but on shared values and behaviors with the sales rep. Think “you like Cobra Kai, so does your prospect”—and it works. Cold calls get longer, more personal, and convert more often.
Results That Speak for Themselves
One customer sent:
500,000 emails using Apollo + Bambora intent → 9 conversions
5,000 emails using Knowledge → 26 conversions
Same copy. Same outbound sequence.
3x more results with 100x fewer emails.
Knowledge has driven:
28% MoM ARR growth
Over 10,000 meetings set in the last year
40%+ conversion rates from email click-throughs
A user base growing virally inside enterprise accounts
Product-Led Growth + “Guerrilla Pilots”
The platform is $79/month per user, with a free trial.
But the real magic? Individual reps at companies like Oracle adopt it on their own. Then others follow. No enterprise deal needed—just value delivered, fast.
Chris calls these “guerrilla pilots.” And once enough reps inside an org are using it, the enterprise sale becomes obvious.
Why AI Still Needs Humans
Chris is clear: AI won’t replace salespeople—it’ll empower them.
He’s betting that the future of GTM isn’t bots talking to bots, but people talking to people—with better tools.
“People want to be sold to by humans who get them,” he says. “Not another AI agent pretending to care.”
Lessons for Founders
Bootstrap early, raise later: Chris self-funded the company to keep control and focus on product-market fit.
Build for where you’re going: Legal, HR, compliance—all were in place before scale.
Invest in relationships: His co-founders, early partners (like ZoomInfo), and investors came from years of relationship equity.
What’s Next for Knowledge?
With real-time Slack alerts, integrations into tools like Clay, and expansion plans into other verticals (fundraising, HR, investing), Knowledge is positioning itself as the infrastructure layer for all human-first engagement.
Think: “the neural engine that powers everything from cold calls to customer retention.”
Final Thought
Whether you're an SDR, a founder, or a sales leader, the takeaway is clear:
Right person. Right time. Right message.
That’s what outbound should be—and that’s what Chris Anzalone built Knowledge to deliver.
👂🎧 Watch, listen, and follow on your favorite platform: https://tr.ee/S2ayrbx_fL
🙏 Join the conversation on your favorite social network: https://linktr.ee/theignitepodcast
Chapters:
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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