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Jason Bay

Outbound trainer who has trained over 200 sales teams, including Zoom, Rippling, Shopify, and Gong. Expert in cold email strategies and sales team leadership.

Top 10 podcasts with Jason Bay

Ranked by the Snipd community
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56 snips
Jul 1, 2025 • 35min

#474 - The Cold Email Strategy That Actually Books Meetings in 2025 | Jason Bay

Jason Bay, CEO of Outbound Squad and a recognized sales influencer, dives into powerful cold email strategies. He introduces three types of irresistible offers that captivate prospects without a hard pitch. Listeners learn the art of the 'blind date meeting' and how to lead with visuals to engage clients. Jason emphasizes utilizing AI for personalized outreach and discusses crafting effective audit offers. He shares insights on enhancing discovery calls and the significance of involving decision-makers for successful pitches.
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48 snips
Jan 20, 2025 • 36min

#415 - Winning Competitive Deals | Jason Bay | 30MPC Hall of Fame

Jason Bay, Founder and CEO of Outbound Squad, shares fascinating insights on navigating competitive sales deals. He emphasizes the importance of understanding why a prospect chose their existing solution to uncover their core motivations. Bay advocates for strategic questioning late in the process to confirm your standing as the top contender. He offers actionable tactics for addressing product gaps and steering conversations to highlight your strengths while exposing competitor weaknesses, ensuring you're prepared to win even in challenging rip-and-replace scenarios.
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26 snips
Jul 8, 2025 • 37min

#476 - The Secret to Writing Better Cold Emails in Half the Time with AI | Sean O’Brien

Sean O’Brien, Enterprise AE at Harvey and former Regional Sales Director at Diligent, shares his expertise on using AI to enhance cold email outreach. He discusses how to harness AI for rapid prospect research and crafting personalized messages. Key strategies include training AI with sales call insights and mirroring prospects' language for higher engagement. Jason Bay, CEO of Outbound Squad, adds insights on the importance of collaboration in outreach efforts. Discover how to streamline your cold emails and see better response rates!
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26 snips
Aug 20, 2024 • 48min

#345 - Sell Playbook: The Definitive Objection Handling Guide (Jason Bay, Outbound Squad)

Jason Bay, an expert in objection handling and sales strategies, joins Nick and Armand to delve into the art of managing objections during cold calls. They discuss transforming objections into opportunities for deeper engagement, emphasizing a genuine dialogue using the 'Mr. Miyagi' framework. The conversation includes techniques for handling budget objections and the importance of personalization in follow-ups. Jason also shares strategies for effectively dealing with gatekeepers, enhancing the chances of successful sales interactions.
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21 snips
Sep 3, 2024 • 36min

#351 - How to Outplay Competitors and Win High-Stakes Rip & Replace Deals (Jason Bay, Outbound Squad)

Jason Bay, a leader in outbound sales strategies and CEO of Outbound Squad, shares his expertise on securing competitive sales deals. He emphasizes the importance of understanding why a prospect's current solution was chosen, which can reveal their motivations. Bay suggests confirming your position with champions late in the deal, and focusing on key product gaps during rip-and-replace scenarios. He advocates guiding prospects to evaluate competitors' weaknesses while highlighting unique strengths, ultimately aiming to forge strong relationships that lead to successful outcomes.
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18 snips
Jul 22, 2025 • 44min

#482 - We Analyzed 85 Million Cold Emails: This is How You GUARANTEE Replies | Sell Playbook

In this discussion, Jason Bay, who trains sales teams worldwide, shares insights from analyzing 85 million cold emails. He emphasizes the importance of brevity, advocating for 4-sentence emails under 100 words to maximize replies. Personalization is key, with tailored messages leading to five times more engagement. Jason highlights the detrimental impact of jargon and salesy language, promoting a buyer-focused approach instead. Actionable takeaways include using the 'Reply Method' framework and effective CTAs to improve response rates significantly.
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14 snips
Jul 15, 2025 • 30min

#479 - 8 Brutal Cold Email Truths That Guarantee Higher Open Rates

In this session, Jason Bay, founder of Outbound Squad and a cold email expert, shares powerful insights on enhancing outreach strategies. He reveals that it’s not AI, but rather poor strategies that hinder success. Jason emphasizes the importance of avoiding asking for meetings in initial emails, as this plummets reply rates. He also discusses eye-catching subject lines, suggesting they should be lowercase and problem-focused. Finally, he offers tips on tailoring messages to boost open rates and engagement.
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11 snips
Jul 24, 2025 • 32min

#484 - Your Reps Fail at Cold Email Because YOU Don’t Teach THIS | Leadership Special

Jason Bay, an outbound trainer with a wealth of experience working with top companies like Zoom and Shopify, joins to share insights on cold email strategies. He reveals why cold emailing is still relevant and outlines a structured four-part framework to enhance effectiveness. Jason emphasizes the importance of understanding prospect personas and delivering personalized messages. He also discusses the value of interactive training and regular reinforcement to help sales teams master their outreach and boost reply rates.
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9 snips
Oct 30, 2025 • 22min

Fixing the Broken Math of Outbound Sales

In this insightful conversation, Jason Bay, founder and CEO of Outbound Squad and a recognized sales influencer, dives into the evolving world of outbound sales. He reveals why traditional cold call tactics aren't cutting it anymore and discusses how to leverage AI for practice, even when live calls are scarce. Jason shares strategies to keep sales reps motivated, effective targeting techniques, and innovative ways to enhance outreach, like using voicemails as marketing tools. It's a fresh take on mastering the art of outbound sales!
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4 snips
Jul 4, 2024 • 34min

#320 - Driving Accountability and Empowering Sales Teams for Peak Performance (Jason Bay, Outbound Squad)

Jason Bay, co-founder of Outbound Squad, shares actionable leadership takeaways for sales teams including setting public goals, utilizing team champions, involving top performers in training, and calculating sales quotas. He emphasizes accountability, collaboration, and practical skills training to drive sales success.

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