Outbound Squad
Outbound Squad
This sales podcast is for B2B reps and sales teams who want to turn complete strangers into paying customers. Join me (you can call me JBay) as I interview sales experts, leaders, and top-performing reps to learn the stories, secrets, and skills of the world’s most successful sales professionals.
Episodes
Mentioned books
7 snips
Nov 25, 2025 • 7min
Biggest mistake when re-engaging closed/lost opps
Clara Johnson, Head of Training at Outbound Squad, shares her sales enablement expertise to help businesses revive closed-lost opportunities. She emphasizes that these accounts are low-hanging fruit waiting for the right approach. Clara discourages routine follow-ups, urging urgency-driven outreach instead. She promotes using AI for personalized messages based on past interactions and highlights the importance of treating old prospects like fresh leads. The key takeaway? Leverage time-based insights and past context to recreate genuine interest.
6 snips
Nov 18, 2025 • 51min
Meet our new Head of Training, Clara Johnson!
Clara Johnson, a seasoned sales leader and former BDR/AE manager from Outreach and Catalyst, joins to discuss her new role as Head of Training. She shares insights on creating a formal outbound methodology and emphasizes the importance of hands-on learning and role-playing in sales. Clara explores the future of outbound sales, highlighting the impact of AI and the necessity for AEs to self-source leads. She also offers career advice and discusses innovative outreach tactics like LinkedIn voice notes, ensuring a human touch in a tech-driven world.
22 snips
Nov 11, 2025 • 51min
Negotiations Masterclass With Todd Caponi
Todd Caponi, an author and negotiation expert known for his works on transparency-based sales, dives deep into effective negotiation strategies. He challenges outdated tactics and emphasizes transparent, customer-focused approaches. Caponi introduces his Four Levers of Negotiating, outlining how elements like volume and payment timing can influence deals. He also discusses how fear impacts pricing confidence and shares insights on when negotiations should truly begin. Caponi's expert tips aim to empower salespeople to protect their value while fostering better client relationships.
6 snips
Nov 4, 2025 • 60min
[Playbook] Steal this PipeGen framework: How we generated $70M+ in new pipeline every week
Marcus Chan, Founder and CEO of Bentley Consulting and a former sales leader, reveals his secrets to generating over $70M in weekly pipeline. He shares his six-step PipeGen framework, emphasizing reverse-engineering activity targets and the importance of team accountability through live scoreboards. Chan discusses creating a focused environment with mandatory prospecting blocks and coaching alongside reps. He also highlights the significance of structured onboarding, hiring for coachability, and removing ambiguity in processes.
13 snips
Oct 28, 2025 • 50min
A masterclass on sales coaching with Mark Hunter
Mark Hunter, a seasoned sales author and consultant, dives into the art of effective sales coaching. He reveals how understanding individual motivators and fostering team culture can transform performance. Daily huddles, energetic leadership, and consistency are key to sustaining engagement and celebrating small wins. Mark emphasizes tailored coaching for each rep, delivering specific feedback, and building rapport. He advocates for diversity in teams and the power of peer training, providing a comprehensive framework for lasting behavior change.
7 snips
Oct 21, 2025 • 11min
How to handle vet AEs who think they know it all
Clara Johnson, Head of Training at Outbound Squad, shares her rich experience in sales to tackle the challenge of getting veteran AEs back into prospecting. She emphasizes using data to highlight the benefits of AE-sourced pipelines, making prospecting time-efficient with short daily sessions. Clara also discusses the importance of teaching AI as a skill, not a crutch, and advocates for a structured approach to AI prompts that ensures quality messaging. The episode is packed with practical tips for engaging seasoned reps.
37 snips
Oct 14, 2025 • 11min
A simple framework to get AEs self-sourcing pipeline
Jason and Clara dive into the importance of AEs self-sourcing their own pipelines in response to industry changes. They discuss how embedding prospecting into weekly routines strengthens accountability, featuring daily huddles and activity updates. Leaders actively participating in prospecting sessions fosters a culture of engagement and commitment. Practical tips are shared on managing meeting loads while making training relevant and impactful. Overall, it’s about aligning leadership behaviors with the prospecting efforts of the team.
5 snips
Oct 7, 2025 • 10min
Improving cold call qualification
Discover how to elevate cold call strategies and boost conversion rates. Explore the importance of asking 'money questions' to pinpoint buyer criteria. Learn about multi-threading and engaging stakeholders early to identify economic buyers. Tactics to avoid empty meetings and ensure real pain is recognized are shared. Clara explains when to qualify prospects during calls and offers practical steps for integrating effective qualification questions into your sales process. Get ready to enhance your outreach skills!
25 snips
Sep 30, 2025 • 1h 2min
[Playbook] Account Executives: Steal this framework to self-source 30%+ of your pipeline (without making hundreds of cold calls)
Join Erika Fuchs, an Enterprise Account Executive at EliseAI, Rob Anderson, Chief Revenue Officer at TitanX, and Darin Alpert, Strategic Account Executive at ZoomInfo, as they dive into the art of self-sourcing. They reveal how top reps can book more meetings without endless cold calls. The trio discusses the evolution of prospecting, effective dialing techniques, and the importance of prioritizing outreach. Discover the psychology behind group emails to C-suite executives and the benefits of leveraging referrals to enhance pipeline efficiency.
14 snips
Sep 23, 2025 • 7min
Cold Calling: Use this intro to book 3x more meetings
Jason shares powerful cold calling strategies to help you triple your meeting bookings. He emphasizes the importance of speaking the buyer's language instead of using buzzwords. The discussion includes practical tips like using reverse pitches and incorporating company-specific details. Real-world examples demonstrate how to avoid typical solopreneur pitfalls and leverage social proof. This insightful guide is packed with actionable tactics that can significantly boost your sales performance!


