How to Cold Call for Higher Connect Rates, Better Conversations, and Meetings That Actually Show Up

Episode Summary

Jason Bay is the CEO of Outbound Squad, where he works with companies like Rippling, Shopify, and Zoom on cold calling effectiveness. In this conversation, he brings real data on connect rates, set rates, and why the gap between average and top-performing teams is widening.

The core argument: cold calling still works, but only for teams operating in the top 10-20th percentile of execution. Average teams are struggling because the bar has risen on data quality, dialer hygiene, and what you actually say in the first 30 seconds.

What We Discuss

Cold Calling Effectiveness Data

• Average connect rate: 5.4% (Gong data)
• Top teams: 13-15%+ connect rate
• Average set rate: 4.6%
• Top teams: 16-18% set rate, some reaching 22-35% with proper enablement
• Half of Rippling’s pipeline comes from outbound cold calling

The Permission-Based Opener

Jason breaks down his PBO framework — a structured way to inject relevance into the first 10 seconds of a cold call. Instead of asking “How are you doing today?”, you lead with something specific to the prospect’s business.

Example for an ecommerce seller: “Hey, I was just on your website and tried to add something to the cart and it didn’t work. Again, it’s Jason with XYZ company. Can I take a minute to share why I called?”

Rethinking the Offer

The biggest unlock Jason sees right now: upgrading what you offer the buyer in exchange for their time. A product demo is no longer enough.

Examples that work:

• Site audits showing load time and checkout issues (ecommerce)
• Mystery shopping competitor analysis (B2B)
• Industry benchmark reports based on real data
• In-person events (executive dinners, networking)

The Future of Enterprise Cold Calling

Jason is candid about the challenges of calling C-suite executives on cell phones. He sees this getting harder over time, especially in enterprise. The phone becomes a tool to support other channels — events, content, referrals — rather than a standalone prospecting method.

Tools and Resources Mentioned

• Outbound Squad — Jason Bay’s training company
• Gong — Conversation intelligence data referenced for connect rates
• 30 Minutes to President’s Club — Podcast with cold calling benchmarks