Traditional outbound is dead. In this episode of AI-Powered Seller, Jake Dunlap reveals how he's getting 5X more meetings with an AI-powered outbound strategy that completely rewrites the sales playbook.

Only 20% of sales teams hit their outbound numbers last year. They're using outdated tactics from when personalization was standard, not the exception.

Jake breaks down his two-part AI outbound strategy:

- How to create personalized white papers for prospects in 20 minutes using ChatGPT
- How to generate custom podcast episodes about your prospect's business in 10 minutes
- Why "automated" killed effectiveness (and how "scalable" brings it back)
- The exact AI tools generating hyper-personalized content with minimal effort

Modern buyers need experts who understand their world. Generic outreach doesn't cut it anymore. Jake demonstrates these techniques live and shows exactly how to implement them on your team today.

Don't let your competitors discover this strategy first. Watch now to transform your outbound approach and start booking more meetings immediately.

New episodes drop every other Wednesday @ 8 AM CT / 9 AM ET

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IT is RUINING many companies’ Generative AI strategy. AI is not just an IT decision. It’s a business decision. But for too many companies, outdated fears and IT roadblocks are sabotaging AI adoption and killing productivity.

In this episode, Jake Dunlap takes on the five biggest barriers IT is putting up against generative AI and lays out exactly how to break through them. Whether you’re a sales rep trying to use AI or a leader pushing for adoption, this is the playbook for moving forward.

Data security & privacy – Why fears from 2023 are holding companies back and what’s actually true today
Integration complexity – Stop overthinking AI strategy and start integrating at the role level
Lack of control – AI outputs are improving fast. Are humans really giving better advice?
ROI concerns – The real numbers behind AI adoption and how to quantify its impact
Ongoing Support & Maintenance – Why AI is easier to manage than most sales tech you’re already using

If your company is dragging its feet on AI adoption, this episode arms you with the facts to push past hesitation and finally implement AI in a way that actually works.

You’ll want to share this episode with your IT team and sales leadership. It’s time to get AI over the hump.


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Sales teams know AI can automate tasks, streamline workflows, and generate insights but most aren’t even scratching the surface of its full potential.

Reps and leaders keep hearing “use AI to sell smarter!” but what does that actually look like in practice? This episode is the tactical breakdown you’ve been waiting for.

Advanced prompting – How using high-quality AI models with better prompts can 10x productivity
Role-based AI agents – The game-changing way to eliminate manual tasks and optimize your workflow
Process automation – Why scaling efficiency isn’t about replacing humans, but working smarter

Jake Dunlap dives into real-world AI applications, from writing a five-page white paper in minutes to automating discovery call prep, and tackles the big question: At what point does AI-powered selling stop being smart and start feeling like cheating?

If AI is going to be your competitive advantage, it needs to be integrated into how you work today, not some future plan.

This episode is your step-by-step guide to making AI work for you right now.

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Connect with Jake: https://www.linkedin.com/in/jakedunlap/

AI isn’t just assisting sellers anymore. It’s stepping into the process in ways that were only theorized about before.

What happens when AI isn’t just assisting sellers but running full inbound sales motions on its own?

That’s the reality OpenAI just put in front of us: an AI-powered B2B sales agent that can take on researching leads, qualifying them, and booking meetings without any human involvement.

This episode will deep dive into Sam Altman’s announcement of OpenAI’s B2B sales agents with Jake’s unfiltered reaction to all that these new tools are bringing to the table. Discover what AI agents mean for the future of sales teams, the roles most at risk, and how AI is reshaping inbound sales.

OpenAI’s latest announcement and why highlighting B2B sales is a major shift
How AI-driven sales agents work and what tasks they’re already automating
The growing gap between companies adopting AI and those falling behind
What sales teams should be doing now to stay ahead of AI-driven automation

Whether you’re an SDR, AE, or leadership, this is news you can’t afford to ignore. No speculation, no hypotheticals. It’s happening right now.

AI IMPACT Report: https://bit.ly/ai-impact-assessment-report

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What happens when AI doesn’t just assist sellers but starts replacing them?

In this episode of AI-Powered Seller, Jake takes a hard look at the timeline: when AI will start automating transactional deals, when mid-level sellers will struggle to stay relevant, and what skills will actually matter in an AI-driven sales world. Forget the distant future. This shift is happening faster than you think. AI is transforming sales in real-time.

But this isn’t just another “AI will change sales” discussion. Instead of his usual co-host, KD, Jake is joined by a different kind of guest: one of OpenAI’s most advanced reasoning models. The goal? Get straight answers on where AI is taking sales and what sellers need to do right now to stay ahead.

What you’ll hear about in this episode:

• The timeline for AI’s potential to replace mid-level sellers (and the roles that are at risk first)
• The three must-have skills sellers need to stay relevant in the AI era
• A roadmap for leveling up over the next 2-4 years and what you should be learning NOW
• How generative AI is boosting productivity (saving hours per week + improving sales quality)

Whether you’re an SDR, AE, or sales leader, this conversation breaks down what you need to do to stay ahead before it’s too late. No scare tactics just a data-backed breakdown that sales professionals need to hear.

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Connect with Jake: https://www.linkedin.com/in/jakedunlap/ 

This episode explores how generative AI is transforming marketing and product development, emphasizing its potential to drive creativity and optimize strategies while underscoring the necessity of human oversight. Listeners gain valuable insights on leveraging AI for impactful copywriting, marketing analysis, and product innovation.

• Generative AI's role in writing compelling website copy and product descriptions
• Emphasizing the power of testing and learning in marketing strategies
• AI's ability to enhance emotional engagement in content creation
• The need for data-driven decision-making in marketing practices
• The interplay of human creativity and AI in product innovation
• Bridging the gap between product teams and customer insights
• Encouragement to embrace AI as a transformative tool for businesses

If you are interested in learning more about leveraging ChatGPT and generative AI for sales, join our workshops!

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Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Connect with KD: https://www.linkedin.com/in/kddorsey3/

Explore the latest advancements in Generative AI, from Custom GPTs to knowledge documents, and how they can transform productivity in sales and beyond. Gain insights into practical applications and features, while discovering new tools to enhance efficiency.

• Overview of AI trends impacting sales
• Introduction to Claude
• New features in the ChatGPT app, including voice interaction
• Benefits and implementation of custom GPTs
• Discussion on knowledge documents and their advantages
• Overview of ChatGPT’s memory functionality
• Tips for maximizing LinkedIn insights with AI

Sign up for the newsletter for free resources on AI trends and best practices!

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Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Connect with KD: https://www.linkedin.com/in/kddorsey3/

Can generative AI truly revolutionize sales, or is customization the secret ingredient to success? Uncover the transformative potential of custom AI models as we explore the pivotal role of data quality in deriving meaningful value from AI implementations. Many teams struggle to see results when applying AI generically; our discussion sheds light on the importance of tailoring AI models to fit your unique business landscape. From understanding sales playbooks and buyer personas to recognizing when to choose custom models over plug-and-play solutions, we promise you'll gain insights into maximizing your AI investments.

Witness firsthand how small, continuous improvements can skyrocket sales rep productivity. Drawing from personal experiences of tripling team production, we highlight the power of incremental progress and the often-overlooked victories it brings. Discover how even AI novices can adopt custom GPT models with ease, thanks to education and non-technical approaches. Our team’s practical steps, including the deployment of AI for scorecards, showcase the incredible time savings and enhanced productivity achievable through tailored solutions. Let us guide you through leveraging AI tools effectively without the technical hurdle.

For leaders and sales teams aiming to boost productivity, creating custom solutions is a game-changer. Learn how even those without technical expertise can harness these tools, focusing on continuous learning and adaptation. We emphasize creating "mini products" as a strategy to tackle organizational challenges, advocating for a gradual approach to tech integration. Through relatable examples, like a customized scorecard system, we demonstrate the capability of AI to streamline processes and identify improvement areas. Finally, embrace the concept of "what good looks like" in business, laying a solid foundation and gradually customizing AI solutions to enhance your strategies without the pressure of perfection.

Join the AI-Powered Seller Newsletter:  https://bit.ly/ai-powered-seller-newsletter

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Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Connect with KD: https://www.linkedin.com/in/kddorsey3/

This episode dives into the transformative potential of generative AI in sales training, focusing on how it can enhance role-playing exercises for sales reps. We discuss practical applications, share insights from real-world experiences, and highlight how to effectively integrate AI into sales processes for skill building.

- Discuss the advantages of using generative AI for role-playing in sales training
- Explore the concept of memory in AI tools and how it aids learning
- Share survey results on the current usage of AI for role-playing among sales professionals
- Emphasize the importance of foundational knowledge in sales personas and objections
- Provide tips for effective role-playing exercises without the pressure of management scrutiny
- Highlight the value of repetition and manual engagement for skill retention
- Discuss the significance of understanding industry knowledge and buyer personas
- Share insights on building and utilizing customized AI prompts for practice sessions

If you are interested in learning more about leveraging ChatGPT and generative AI for sales, join our workshops!

Join the AI-Powered Seller Newsletter:  https://bit.ly/ai-powered-seller-newsletter

Sign up for Custom GPTs: https://link.meetjourney.ai/aff_ad?campaign_id=4859&aff_id=2751&source=Jake-KD-Podcast&hostNameId=24435

Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Connect with KD: https://www.linkedin.com/in/kddorsey3/

Can AI transform your sales enablement into a powerhouse of performance? Discover how leveraging AI-powered infrastructure can lead to remarkable improvements in sales outcomes. Our latest episode promises a lively discussion that kicks off with personal New Year's stories before diving into the essential transition from traditional sales enablement to an AI-boosted strategy. We unpack the critical components needed for this shift, emphasizing the importance of generative AI in daily operations. This isn't just about gathering data—it's about turning data into actionable insights that truly enhance productivity.

Join us as we explore the concept of enablement within sales and revenue, where the action of making something possible has never been more vital. We'll tackle the challenges faced by enablement teams and the crucial role of leadership, especially from the Chief Revenue Officer, in ensuring strategies are aligned and effective. Learn about innovative AI tools like quiz GPTs and coaching bots that are revolutionizing sales enablement by offering ongoing feedback and reinforcement. Tune in to hear how even resource-constrained teams can see substantial performance gains by embracing these technologies. This episode is a must-listen for anyone looking to harness the power of AI to supercharge their sales strategies.

Join the AI-Powered Seller Newsletter:  https://bit.ly/ai-powered-seller-newsletter

Sign up for Custom GPTs: https://link.meetjourney.ai/aff_ad?campaign_id=4859&aff_id=2751&source=Jake-KD-Podcast&hostNameId=24435

Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Connect with KD: https://www.linkedin.com/in/kddorsey3/