The Playful Integration of AI in Sales

Everyone's talking about how amazing AI can be, but there’s a real dearth of actionable advice on how to actually put generative AI to work for your sales, marketing, customer service, or other go-to-market team. Well, that was until we talked to this week’s incredible guest…

Jake Dunlap is truly a thought leader on using AI in B2B go-to-market strategies and is the CEO of Skaled Consulting, a revenue performance agency dedicated to helping B2B companies scale smarter. Jake joins Matt Amundson and Craig Rosenberg to delve into the tactical and practical ways he is implementing AI tools into go-to-market motions and how you can get the benefits of new AI technology. Jake and Matt have both been building some interesting agents and custom GPTs, and they get into how they set them up and how they are using them. Jake discusses why B2B sales leaders need to stop managing by measuring sales rep activity, how to avoid major pitfalls when implementing generative AI tools in your organization, and how to build an efficient and effective outbound strategy today. 

Also, Craig shares that both of his cars were stolen straight out of his driveway, Matt remembers the name of a consumer product, and Producer Sam interrupts to ask a question about podcasts.

Critical Takeaways

• Train your sellers to think critically. Don't just provide templates. Teach your sales team how to analyze trends, customize outreach, and add value based on their understanding of the buyer's industry and challenges. Encourage creativity and problem-solving skills.
• Measure outcomes, not just the activities of your sellers. Shift your focus from tracking the sheer volume of sales activities to measuring meaningful conversations and outcomes. The quality of interactions should take precedence over the quantity.
• Start using AI to improve bottlenecks that you or your team are facing. While there are myriad amazing things you could do with AI, by focusing on the boring, unsexy things that constrain your revenue team, you’ll actually drive greater outcomes for your team.
• Sellers, try doing the type of outreach that isn’t massively scalable, but that provides immense value and really sticks out. This is likely going to yield better results than hitting ‘send all’ again. For example, you could use new AI tools like Deep Research and NotebookLM to create customized podcasts and white papers tailored to the specific role and industry needs of a contact at a target account.
• AI is not a go-to-market strategy in and of itself, nor is it something that can be applied in a blanket fashion across every role or function. 
• Let sellers play to their strengths. For example, some reps are great on video, while others excel on the phone. Don’t force every sales rep into the same volume-driven mold. Focus on outcomes, not activities.
• Don’t wait for Enablement to hold your hand and train you on using AI. As Jake said, “ sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.” Why is that? Because AI is more than just another tech tool, it’s a fundamental shift in problem-solving. Don’t sit around waiting for a playbook—experiment, build, and iterate. Training wheels are for losers… and small children.

Chapters

00:00 - Episode Preview

00:36 - The Fast & The Furious: Silicon Valley Drift

07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI

11:41 - Why B2B Sales Reps Need to Start Using AI for Account Research & How to Get Started with New AI Tools 

13:36 - How to Build AI Agents for Each Buyer Persona & How Matt is Using AI as a Chief Marketing Officer

16:08 - The Power of Building Custom AI Agents for Revenue Growth

22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact

30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market

37:01 - How Will Anthropic and OpenAI’s Custom GPTs Integrate with Existing SaaS Tools & Will Gen AI Tools Replace the Go-To-Market Function as We Know It?

42:01 - What Hurdles to Avoid When Implementing AI Tools in Your Company & Why Leaders Need to Stay on Top of AI Advancements

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Epic Quotes

• “Stop asking the question, ‘What’s our AI go-to-market strategy?’ It’s not the right question.” - Jake Dunlap
• “The goal are the outcomes, not the activities.” - Jake Dunlap
• “Outbound never ends. You cannot take a project-based mindset to outbound.”  - Jake Dunlap

Connect with Jake Dunlap

• LinkedIn: https://www.linkedin.com/in/jakedunlap/ 
• Website: https://skaled.com/ 
• The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller 

Shoutouts

• Dirty Mike and The Boys: https://youtu.be/1FkK8ZFE7Y0?si=WpJ9miacA2CdLq0u 
• NotebookLM: https://notebooklm.google/ 
• The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/03F3RE2 
• Matt Heinz: https://www.linkedin.com/in/mattheinz/ 
• Matt’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/how-to-implement-ai-in-your-go-to?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• Sydney Sloan: https://www.linkedin.com/in/sydsloan/ 
• Sydney’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• The Club: https://store.winner-intl.com/the-original-club-p2.aspx 

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