Actually Actionable Advice For Implementing AI with Jake Dunlap - Ep 59
Plus, How to build an Outbound Strategy for today
Welcome to the latest weekly edition of The Transaction newsletter & podcast. Every Thursday, we share resources you should check out, what we’ve found insightful recently, and tactical ways you can improve your go-to-market today. For more: Podcast | YouTube
Ooooh boy folks, this is by far the longest, most insightful, and action-packed edition of the newsletter we’ve ever done, so let’s cut the chit-chat and get down to business.
Here’s what’s on deck this week:
What Craig’s Reading (2x)
Recent Insights from Past Guests: Brent Adamson, Jordan Crawford, and Dave Brock
Latest Episode: Actually Actionable Advice For Implementing AI with Jake Dunlap - Ep 59
The Direct Deposit - Ep 1
Movie Poster Mockup: Gone in 60 Seconds
Did someone forward you this newsletter? We’re terribly sorry about that, but since you’re here, you might as well subscribe…
What Craig’s Reading
I love you, Figma ❤️ – but what’s with these DUMB retention metrics 🤮 in your S-1?!!! By David Spitz
If you don’t follow Spitz, you should. He is doing amazing analysis of the software market and sharing a lot of his work on LinkedIn. This is about the Figma NRR and GRR numbers in their S1. I would read the article, but in the meantime, here is a snippet: “Figma starts with customers from today and looks back — only at the ones they also had a year ago. They miss counting the churn from customers from a year ago, who subsequently churned.”
The Activator Advantage by Matt Dixon (A Previous Guest)
Just started so I will let you know next newsletter.
Recent Insights from Past Guests
Brent Adamson, Currently with Qoos. Most known as the co-creator of the Challenger Sale - Brent’s Episode
Jordan Crawford, Founder at Blueprint - Jordan’s Episode
Dave Brock, Founder of Partners in Excellence - Dave’s Episode
Dave poses an interesting hypothetical…
Latest Episode: Actually Actionable Advice For Implementing AI with Jake Dunlap - Ep 59
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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 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
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
Shoutouts
Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
The Direct Deposit - Ep 1: What Made RevFest 2025 Such a Great B2B Event?
In case you missed this on Craig’s LinkedIn, we’re rolling out a new product as part of The Transaction, called… The Direct Deposit: Quick hits, tons of insights. Learn something in 5 minutes that will help you towards your numbers this quarter.
Movie Poster Mockup: Gone in 60 Seconds
In honor of Craig having both of his cars stolen right out of his driveway. So damn funny.
Sponsored Segment
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Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com
Follow the Hosts
Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/
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