Outbound Squad

Kyle Vamvouris, founder of SalesThread and AI practitioner focused on conversational intelligence for sales. He discusses making AI simple for reps and building agents to extract structured call data. He explains scoring rubrics, objection detection, and how AI could replace routine deal support and reshape RevOps and management spans.

Calvin Flax, a sales development manager at ZoomInfo who coaches SDR teams, and Jason Bay, a sales trainer and CEO of Outbound Squad, break down how to win high-quality meetings. They tackle why outbound is harder today. They discuss refining target accounts, crafting offers that get prospects to say yes, data-driven outreach, an F-shape email framework, and using AI responsibly to scale personalization.

Nate Vogel, a sales enablement leader who built programs at Tableau, Salesforce, Gong, Databricks and Pigment. He breaks down building scalable enablement with data-driven rollouts, prioritizing managers to multiply impact, practical measurement approaches, conversational intelligence insights, reinforcement after kickoff, and practical AI uses for coaching and localization.

Bert Brokaw, Senior SDR Director at Rippling who builds and scales large outbound SDR teams. He discusses Rippling’s shift to outbound and rapid scaling. He talks hiring fit when moving inbound reps to outbound. He covers enablement, ops and marketing specialization. He outlines leadership transition, manager development, and a practical weekly rhythm.

A conversation about why leaving enablement out of sales strategy backfires. Stories about enablement that actually works, including specialization and data-driven advising. Examples of live skill demonstrations and sharing the stage with top performers. A strong case for prioritizing manager enablement as the highest-leverage approach.

Discussion of hiring trends showing AI companies still recruit human outbound reps. Examples of OpenAI and peers building sales development teams are highlighted. Experiments trying to fully automate outreach and their failures are described. Emphasis on the advantage of reps who become fluent with AI tools.

Jason Bay, CEO of Outbound Squad who trains sales teams on cold-calling frameworks. He breaks down permission-based openers and problem-focused messaging. He explains phone strategy, the reverse pitch, and ways to harvest customer language. He covers coaching rhythms, rep diagnostics, and tactics to boost meeting show rates.

In this episode, Aaron Rissler shares his journey from IC to VP of Sales at Buyer's Edge Platform, revealing the lessons, strategies, and leadership insights he’s learned along the way to build high-performing teams, navigate corporate politics, and level up at every stage of a sales career. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

This episode is the audio from our recent webinar on The Outbound Equation. Jason walks through a proven methodology for securing high-quality meetings in 2026 by reinforcing fundamentals like offers that deliver real value, world-class execution on phone, email, and social, and the critical role of leadership in creating predictable outbound pipeline. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Bryan Evans, VP of Sales at Neo4j and seasoned sales leader who rose from rep roles, shares leadership habits and practical routines. He covers deal qualification and when to get hands-on. He explains forecasting discipline, CRM rigor, and running accountability reviews. He talks about building pipeline accuracy, multi-threading into accounts, and keeping cross-functional partners aligned.