May 23, 2026 | Read online
Helping elevate the people and profession of Sales by sharing authentic conversations, practical tips, expert advice, relevant tech and real-world lessons from my experience selling every day. Delivered to your inbox every Saturday.
Jobs vs Tasks
I’m trying something different with this week’s newsletter.
It’s one of those “learning out loud” moments that I’m doing with the JB Sales Learning Lab.
I’m trying to find the balance of leveraging AI the right way (in my opinion) to create interesting and valuable content while maintaining authenticity.
I’ve seen a lot of AI slop out there on Linkedin, newsletters and emails where it’s pretty obvious AI was used to create and automate the content. Some people I know and respect are now cranking out 5-10 long format pieces on LinkedIn every week and I KNOW they don’t have the time to do that so therefore I know they’re using AI.
It’s not that the content is bad or not valuable, it’s just that it loses its value for me when I can tell it’s been mostly generated by AI.
I’m also seeing a huge backlash on people who are absolutely sick of AI generated content/slop.
However, I do feel that when AI is used to help ideate, brainstorm, research and organize information, it can actually help create better content as long as the human stays in the loop throughout.
As most of you (should) know, I usually write all my own posts, and especially my newsletter, without using AI and try to stay as authentic as I can.
However, from time to time, I need a little help flushing out some ideas I have about content that I think would be interesting to my audience.
So, I decided to use this newsletter to show you my approach to how I use AI to ideate and develop content while trying to maintain the authenticity and human element.
I ended up recording the process that you can watch at the end. Below is the final draft that I wrote WITH AI. Let me know what you all think.
SPOTLIGHT
Before we get into it, I recently sat down with Val Riley on Insightly's Closing Time podcast to break down the five-step prospecting framework I’ve been refining for more than 25 years.
We talked about why most reps start outreach before they actually understand who they’re targeting, why your ICP should live dynamically inside your CRM, and how AI is completely changing the way top reps research and prepare for conversations.
One of the biggest themes was that AI doesn’t fix broken prospecting fundamentals, it just scales them faster. If you want a deeper dive into how I’m thinking about AI, prospecting, and building pipeline right now, check out the full episode.
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I’m trying to keep up to date with how fast things are moving in the world of AI and identify the information I think is important for me and my audience to pay attention to.
With that, my Instagram feed is filled with content about AI, all the way from doomsday scenarios where robots take every job on the planet to utopian visions where nobody ever has to work again.
The doomsday content far outweighs the utopia content, and it’s been getting pretty dark lately, which is starting to freak me out if I’m being honest.
However, there are some posts that give me hope, and I came across one of them the other day that I thought was worth exploring more.
I saw a clip from an AI researcher where he was explaining why he wasn't worried about AI taking over everyone's jobs. His argument was that there's a difference between a job and a task.
AI is incredibly good at doing tasks, the repeatable, structured things that make up part of your day. But a job is more than a collection of tasks. A job requires judgment, relationships, adaptability, context, and the ability to pull all of those things together in real time. AI is not good at doing the job (at least not yet). It's great at doing pieces of it.
That concept somehow made me feel a little better and is one that I wanted to explore more, but then I got distracted and lost the video in my feed and had to move on to other work.
When it came time to sit down and write my newsletter, I thought it would be a good topic to share my thoughts on, but I had lost the video and didn’t have much of an opinion to share, just a nagging interest in a topic that I thought was hopeful and interesting.
So instead of sitting down and writing this newsletter from scratch on my own, I decided to do something different. I opened up Claude and started working through this concept with AI as my thought partner. Not to write this for me, but to help me develop the idea further and faster than I could alone.
Here's what I think is important about that. I'm not using AI to replace my thinking. I'm using it to sharpen it. AI didn't come up with the angle for this newsletter. I saw the clip, I had the reaction, and I knew there was something worth exploring. But AI helped me research, validate, pressure-test, and build on that idea in a fraction of the time it would have taken me to do it alone.
That's the model I believe in: human-led, AI-amplified. The human brings the instinct, the experience, and the point of view. AI brings the speed, the research, and the ability to organize information at scale.
So here's the process I went through, and here's what we came up with.
First, I told Claude about the clip and asked him to find the source. I wanted to make sure I wasn't about to build a newsletter around something said by someone with no credibility. It came back with Andrew Ng, a Stanford professor, former head of Google Brain, and one of the most respected AI researchers in the world. Solid source. I felt good about running with it.
From there, I wanted to apply this "jobs vs tasks" concept to something specific. I picked the SDR role because it's the one most people in my audience either do, manage, or have done at some point. I had Claude research SDR job descriptions across SaaS companies, find the commonalities, and then break down which parts of the role are tasks that could be automated and which parts are the actual job that requires a human. The breakdown was interesting.
We’ve all heard those stats before about how SDRs spend about 72% of their day on tasks like research, data entry, email drafting, and sequencing. The actual job, the conversations, the qualifying, the relationship building, the judgment calls, that's the other 28%. It’s also where the real value is created and why I don’t think AI will replace the “job” of an SDR (yet).
So the question becomes: if AI can handle 72% of what you do today, what do you do about it? Do you wait for your company to figure it out and hand you the tools? Or do you take ownership and start building your own system?
I personally don't have a ton of faith that most companies are going to get this right on behalf of individual reps. It's not that they're being malicious. Most of them are trying to figure this out just like the rest of us in an environment that is constantly changing, which makes it almost impossible to figure out the best approach.
They're buying AI tools, plugging them in, and hoping the technology fixes what is actually a training and enablement problem. They're automating broken processes and wondering why the output is still broken.
So my advice is to take ownership. Here's the process I'd recommend for any rep in any organization right now.
Use AI to learn, not to skip. There's a massive difference between telling AI "write me a prospecting email" and using AI to actually understand your buyer's world before you ever write anything. Here's what I mean.
Let's say you're an SDR going after VPs of Sales in SaaS. You could ask AI to write you ten cold emails and start blasting them out tomorrow. Or you could start by asking AI to research your accounts and come back with five or ten trigger events that would actually give you a reason to reach out.
Let’s say AI comes back, and one of the trigger events is a merger and acquisition. Now, instead of having AI write the email for you, use it to go deeper, learn more, and improve your business acumen so you understand WHY an M&A is a good trigger to use, specifically for that persona.
You can/should ask AI to help you understand what a VP of Sales at a $10 million company is actually going through when they get acquired by a billion-dollar company. What are their fears? What are they being held accountable for? What opportunities are they trying to protect? What's happening to their team, their comp plan, their pipeline? AI can help you map all of that out in minutes.
From there, you start connecting the dots. How does your solution actually help that specific person in that specific moment? Have you helped other companies going through something similar? If so, what happened and what did the results look like?
Now you're building a real understanding of your buyer's situation, and THAT is what makes the email worth reading. Not because AI wrote a clever subject line, but because the person reading it can tell you actually understand what they're dealing with.
That's the difference between using AI as a shortcut and using AI as a coach. The shortcut gives you an email. The coach gives you the judgment to know why that email works, which means you can have a real conversation about it when the prospect picks up the phone and asks, "How do you actually help with that?"
Once you start thinking about AI that way, the next step is to look at where your time actually goes. Track it for a week. How much of your day is research, data entry, email drafting, and scheduling versus real conversations, qualifying, and relationship building? Most reps are shocked when they see the split.
Then automate the tasks, not the thinking. Use AI to compress the research, draft the first version, update the CRM, and organize your pipeline. But you are the one reviewing, LEARNING, adjusting, and making the final call before anything goes out. That's how I run my own system. AI surfaces the accounts, builds the sequences, and drafts the emails. I review every single one before it sends. Augmentation, not automation.
And never stop developing the fundamentals. The rep who stops learning because "AI handles it" is the one who gets replaced. Not by AI, but by another rep who uses AI and understands the process underneath it.
Andrew Ng's line is one that I have used before and still believe: AI won't replace you, but someone who uses AI will. The keyword in that sentence isn't AI. It's "uses." Using it well means understanding what you're automating and why. It means knowing the process before you hand it off to a machine.
This entire newsletter was co-created with AI. I brought the idea, the instinct, the experience, and the voice. Claude brought the research, the validation and helped me pressure-test the framework. Neither of us could have produced this alone as fast or as well as we did together.
If you want to see exactly how that process worked, I recorded the whole thing here. Watch me go from a random Instagram clip to a fully developed newsletter concept in real time. It's not polished or edited (much). It's the raw process of how I use AI as a thought partner every single day.
I'd love to hear what you think. Did this land? Was it valuable? Could you tell if it was co-authored with AI? Hit reply and let me know. I'm genuinely curious whether this format works for you, because if it does, I'll keep showing the process behind the content, not hiding it.
#MakeItHappen