Outbound Squad

Keith Weightman, RVP of National Accounts at Bullhorn, specializes in coaching and sales leadership. In this conversation, he shares insights on fostering a coaching culture that benefits both reps and leaders. He highlights effective strategies for impactful discovery calls, emphasizing preparation and stakeholder involvement. Weightman also discusses the importance of continuous improvement and curiosity in sales, and how to build trust with clients through storytelling and insightful questioning, transforming the sales experience.

Leslie Venetz, an expert in modern outbound strategies and author of 'Profit Generating Pipeline', dives into the pitfalls of traditional sales wisdom. She emphasizes the importance of building genuine trust and defining your ideal customer profile. Leslie critiques the vague messaging often seen in sales, advocating for strategic segmentation to enhance outreach. She also discusses the critical balance between product and customer voice in sales messaging and underscores the necessity of soft skills in fostering meaningful connections.

Kyle Norton, CRO at Owner.com and a seasoned sales leader, teams up with Diana Gates, Head of North American Sales Development at Shopify, to explore the intricacies of building an effective outbound sales program. They discuss the importance of collaboration between sales and marketing for lead generation, innovative strategies like hypersegmentation, and the critical role of understanding team dynamics. The duo also shares insights on simplifying customer options and the necessity of measurement in enhancing outbound success.

Chris Bussing, a tech sales expert and host of The Chris Bussing Podcast, shares impactful strategies to elevate cold calling and outreach. He discusses the 'Reason to Meet' strategy for booking more meetings and emphasizes the importance of human intuition alongside AI tools in sales. Listeners learn about effective cold calling techniques, overcoming mental barriers, and the reverse pitch approach to engage clients. Bussing also highlights the role of coaching in achieving sales success and personal development, making this a must-listen for aspiring sales professionals.

Scott Lease, CEO of Scott Lease Consulting and a six-time VP of sales, teams up with Jonathan Lister, COO at Vidyard and former leader at LinkedIn. They share expert techniques for engaging C-suite executives, focusing on building relationships and understanding their priorities. Discover strategies for cold calling, navigating internal referrals, and the significance of multiple champions in closing large deals. The conversation emphasizes the importance of tailored communication and how to effectively master interactions with top decision-makers.

Join James Buckley, a sales expert and content creator, Jed Mowerly, founder of Practical Prospecting, and Will Aiken, video technology innovator from Viddo, as they tackle the modern challenges of meeting bookings. They discuss innovative strategies for outreach, stressing the importance of personalization and adapting to shifting buyer behaviors post-COVID. Discover how AI tools can boost efficiency in prospecting and learn unique tactics for engaging potential clients via LinkedIn. Building trust and understanding competition are highlighted as keys to sales success.

In this episode, Jason shares the seven hard truths about outbound in 2025 and how to adapt to stay ahead.Check out the show notes, more free content, and get coaching at https://outboundsquad.com

Nick Cegelski, founder of 30 Minutes to President's Club, and Waseem Kaati, lead mid-market sales acquisitions at Shopify, offer fresh insights into cold calling. They discuss mastering effective cold calling techniques, emphasizing preparation and strategic questioning to secure meetings. The duo explores the role of 'invisible scripts' in shaping sales interactions and how to leverage data for personalized outreach. Listeners will learn about crafting impactful sales conversations, utilizing problem-based language, and overcoming objections to enhance engagement.

Discover the secrets behind effective sales messaging and learn about 'levels of relevance.' Master targeted outreach with strategies like industry-based account grouping. Dive into the role of AI in personalizing communications for maximum impact. This conversation offers actionable insights to elevate your outbound game.

Discover the secret strategies top Sales Development Representatives use to connect with buyers. Learn how to stay attuned to challenges facing prospects to boost sales effectiveness. The conversation dives into five actionable habits that can enhance outreach and help meet quotas. Get ready to level up your sales approach by focusing on the heart of the buyer's issues!