Welcome to Lead with AI, the only executive AI brief for busy leaders. Every Thursday, I deliver the latest AI updates through real-world insights and discussions from our community of 170+ forward-thinking executives.
For today:
- Entry-Level Jobs Are Vanishing: AI is erasing early-career roles—here’s what smart companies and future employees must do next.
- "AI for Dictation" Essentials: Wispr Flow and Granola AI
- 3 Must-Read AI Stories: ChatGPT Gains Enterprise Traction, AI Becomes Job Requirement, Fine-Tuning Turns AI into Your Edge
- Prompt of the Week: Make Tough Decisions with AI
Before we dive in, just a quick heads-up: Enrollment for my Lead with AI June cohort closes tonight at midnight. If you’ve been meaning to join but haven’t grabbed your spot yet, this is your last chance. Grab one of the few remaining seats with my special $199 OFF offer using this link!
LAST CHANCE: Sign up for June cohort
Let's dive in:
Practical Tips for the AI-Driven Workplace
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“Your AI Team” Platform Updates
Essential updates from our core AI platforms can mean big changes in your and your team's productivity. Here's what's new from the essential AI tools that most Lead with AI leaders are using:
AI Kills 50% of Entry-Level Jobs — So What Do We Do Now?

Anthropic CEO Dario Amodei caused commotion, at least in my corner of the internet, when he told Axios that “AI may wipe out 50 percent of entry-level white-collar roles within five years.”
Fresh data suggests he might be right:
- Big Tech graduate hiring is down by 50% since 2019 (SignalFire).
- Meta’s Mark Zuckerberg said AI will soon handle “mid-level engineer” work.
- ServiceNow agents already resolve 80% of support tickets unaided.
- An EY survey reveals that 48% of tech executives are deploying agent-based AI.
- Salesforce is redeploying 500 service reps into “data-plus-AI roles.”
Together, the signals point to a “broken bottom rung on the career ladder,” as LinkedIn’s Chief Economic Opportunity Officer, Aneesh Raman, wrote in The New York Times:
“In tech, advanced coding tools are creeping into the tasks of writing simple code and debugging — the ways junior developers gain experience. In law firms, junior paralegals and first-year associates who once cut their teeth on document review are handing weeks of work over to A.I. tools to complete in a matter of hours. And across retailers, A.I. chatbots and automated customer service tools are taking on duties once assigned to young associates.” – Aneesh Raman, Chief Economic Opportunity Officer, LinkedIn
So what does the entry-level job of the future look like, and how do we (workers and companies) get there?
Let’s dive in.
The New Entry-Level Job
I liked Josh Bersin’s counter to Amodei’s prediction that entry-level jobs are about learning and building a pipeline, not just cheap labor. And that cutting them creates long-term skill gaps.
This is something LinkedIn’s Aneesh Raman also highlighted: getting started later means less money and more inequality.
I’m also puzzled by what entry-level jobs are, anyway. Any first job that people (eventually) take is entry-level. How can they go away?
But yes, if we interpret those as the kind of roles Raman describes, I do think Amodei’s “50%” is directionally right. Jobs where you’re just copy-pasting, summarizing, or creating first drafts will become obsolete with AI.
However, in its place will be ‘first roles’ as ‘AI leaders' that young candidates are ideally suited for.
They enter the workforce as AI natives, and in fact, can teach today's leaders a lesson or two (reverse mentoring).
This is a place where graduates can actually have a significant advantage: Sam Altman recently remarked that younger AI users often tap it as a new kind of operating system, rather than a Google replacement.
These are the kind of people that employers are hungry for, as evidenced by Zapier CEO Wade Foster, who stated that 100% of new hires must be fluent in AI.

Because, as I recently stressed in my articles Prompt Engineering Isn’t Dead and You’re Only Using 10% of ChatGPT, AI still needs direction.
Today’s models are incredibly powerful. I’ve been working more with o3, and it amazes me what a reasoning model + tools can do. But no matter how impressive, they still need direction.
“The machine can do anything, now what do you want them to do?”
Tapping AI as a team member and prompting them well is key, alongside proficiency in tool fluency, to start or continue any career.
Even Amodei told Anderson Cooper so: the best hedge to future disruptions is simply “learn AI.”
That message is loudest for fresh graduates who now know what employers value:
- Baseline expectation: Do you know how to prompt, set up a simple assistant, and leverage different models? (See my new ChatGPT course if you need help.)
- Become a SuperWorker: Use my GED-RT framework (General, Error-friendly, Digital, Recurring, Toil) to identify tasks that AI (beyond ChatGPT) can handle today.
- Show real projects: custom GPTs, automations, and prompt libraries: proof you can tailor these models for real productivity and impact. (the stuff we do in the Lead with AI executive bootcamp.)
Do so, and graduates may even agree with PwC, which said they’re “lucky to be starting their careers as AI accelerates.”
Companies
But this discussion isn’t just about what people can do. It’s also a call to action for companies to get serious about AI at all levels:
- Name the risk in entry-level roles. As OpenAI writes in its playbook Identifying & Scaling AI Use Cases, jobs vanish only for people who never use AI.
- Recruit new team members who are AI-fluent, or at least (like I do), hire for the willingness, mindset, and attitude to work with AI.
- Encourage reverse mentoring. Sophie Wade said in an interview that “Many leaders are missing out on the contributions of their youngest employees who have a feeling for the power of technology that we just can’t have.” Tap into that.
- Upskill throughout. As OpenAI suggests, teach at least the six AI primitives (content, research, code, data, ideation, and automation).
- Get everyone building. Run a GED-RT sweep team-by-team to find low-joy, high-repeat tasks, and find quick wins just as Moderna went from 750 to 3,000 GPTs and J&J pruned 900 experiments down to the 15% that drove 80% of value.
SHRM Foundation Chair and Future of Work expert Edie Goldberg underscored the imperative for companies to rethink entry-level positions in exclusive commentary for this newsletter:
“Entry-level jobs are changing, but we need to rethink how people learn the business and build functional expertise. Research shows that AI is especially helpful for lower-performing employees—often those who are just starting out—because it provides access to the knowledge that drives success. Entry-level roles aren’t disappearing, but they are evolving. We need to evolve our thinking with them.” – Edie Goldberg, the Immediate Past Chair of the SHRM Foundation Board of Directors
Don’t Get Left Behind
The bottom line is that AI will eventually disrupt all jobs, and therefore, AI mastery is critical for everyone, from recent graduates to seasoned executives.
Students and graduates should prepare themselves to be as attractive in the market as possible by studying up on AI.
Companies should ensure they’re ready to hire those who are most likely to drive AI adoption and culture.
So, pick one GED-RT task this week, replace it with a prompt-plus-tool workflow, and demo the result—then repeat. The ladder may be shorter, but it climbs faster if we rebuild it now.
Category Essentials: AI for Dictation
Each week, I spotlight one category and suggest the three tools that are tried, tested, and trusted by Lead with AI members.
For this week: More and more of us are ditching the keyboard and speaking instead. Not because it’s trendy, but because it’s faster, more natural, and often closer to how we actually think.
This week, I’m only featuring two tools—not the usual three—because these are the ones our community actually keeps using and talking about.
Flow (by Wispr)
This one’s quietly become our go-to for writing by voice.
It’s a desktop and now iPhone app that turns your speech into clean text, with much higher accuracy than the usual built-in dictation tools.
Our community member Joe Harris says it’s helped him cut through email and RFPs in half the time. It filters out all the “umms” and “likes,” learns the words you correct (like niche product names), and pairs well with Grammarly for final polish.
Michael Brooks, a Dragon Dictate–turned–Wispr user, says it’s far more accurate, yet still notes a couple of quirks: you won’t see the text until you stop speaking, and some formatting takes getting used to.
>> Try Wispr Flow here. (Freemium available)
Granola AI
If Flow is for writing, Granola is for listening. It runs quietly on your computer and helps you get structured notes.
Earl Hoeg shares that he likes the meeting templates that auto-adapt based on the context, whether it's a one-on-one or a client check-in. If your days are full of back-to-back calls, this can save you a lot of context-switching.
One feature Wendy prefers in Granola over other AI meeting notetakers is that you can just run it in the background for any conversation, even in person (It has an iPhone app, too).
Still, a reminder: Always ask permission before transcribing to others!
>> Try Granola AI here. (Freemium available)
>> Want more community recommendations for AI meeting transcripts and summaries, check out this "AI for Meeting Notetakers" category!
Want me to cover a specific category and/or AI tool next? Reply and let me know here.
The AI Executive Brief
ChatGPT Gains Enterprise Traction, AI Becomes Job Requirement, Fine-Tuning Turns AI into Your Edge
I read dozens of AI newsletters weekly, so you don’t have to. Here are the top 3 insights worth your attention:
#1 3 Million Businesses Now Pay for ChatGPT

OpenAI just hit 3 million paying business users—up 50% since February. Customers span from Morgan Stanley to Lowe’s to Uber, even in tightly regulated sectors like finance and healthcare.
New workplace features dropped too: “connectors” let teams pull live data from tools like Google Drive and SharePoint into ChatGPT, and a new “record mode” helps transcribe and turn meetings into docs.
👉 Watch full ChatGPT for Business updates here
#2 “AI-First” or Out?
Duolingo, Shopify, Box, and others are taking a bold stance: AI is no longer optional. From hiring and performance reviews to daily workflows, employees are expected to integrate AI, or explain why not.
The shift is real: AI is now seen as a baseline skill at work. Some call it urgent upskilling. Others worry it’s “AI over people.” Yet, Klarna’s case reminds us: even when AI boosts efficiency, overreliance without thoughtful balance can backfire, especially where human judgment still matters.
👉 Read the full discussion here, and I'm curious to hear your take in the reply.
#3 Fine-Tuning Is How You Make AI Your Own
In his latest piece, Microsoft's CMO, Jared Spataro, argues that when everyone has access to AI, advantage comes from how you adapt it.
Fine-tuning lets you embed your company’s language, workflows, and judgment into the tools your teams use. This way, you're turning AI into a carrier of institutional knowledge. His framing is sharp: let agents specialize (go vertical), so humans can step back, connect dots, and steer (go horizontal).
Prompt of the Week
A good prompt makes all the difference, even when you're just using a core LLM.
Ali Abdaal inspires this week's prompt: use AI not to get the "right" answer, but to see both sides of a question clearly. Sometimes, what you really need isn’t advice, it’s perspective!
You can prompt AI to take on a specific persona—like a blunt drill sergeant—and make strong arguments for and against your idea. The contrast helps sharpen your own thinking.
Try on Different Perspectives with AI
I want you to take on the voice and mindset of a brutally honest drill sergeant. I’m going to tell you something I’m struggling with, and I want your no-nonsense take on what I should do—even if it’s harsh.Then, I want you to make an equally compelling argument for the opposite approach, from the same persona. Make it convincing. I’m not asking for the ‘correct’ answer—I want to hear both sides with strength and clarity. My goal is to see the trade-offs clearly so I can decide for myself.
You can use this on anything: product decisions, content plans, hiring questions, even creative blocks. It’s to help you see more clearly so you can make tough decisions (quicker).
👉 Try it, tweak it, and save it for your future use. If this prompt is helpful (or if you made it better), I’d love to hear how.
👉 Want a free prompt library template? Reply with one thing here, and I’ll send it your way.
AI for Strategy, Responsible Adoption, and Prototyping: From the Community

Every day, Lead with AI PRO members discuss practical ways to benefit from AI in their work and organizations. This week's highlights include:
- If you had $1,000/month to spend on AI tools for yourself, how would you use it? - Wendy McEwan posed. The answers, as you’d expect, varied by role and workflow, but Wyatt Barnett gave us a full-stack tour of his AI essentials:
- Perplexity as his “fact book”
- Suno as his personal DJ
- Claude for marketing copy and MCP stunts
- Leonardo for visuals (once ChatGPT’s image model got too slow)
- Airtable and Supabase for data handling
- Zapier and Make for simple automations
- Cloudflare as his go-to dev platform, with DigitalOcean as a strong option “if you’re a Pythonista”
- I shared the newly released “Trends – Artificial Intelligence” report by Mary Meeker team with the community. And Wyatt suggested bundling it with key reads like Stanford’s AI Index Report for a fuller picture.
Don't want to miss more insights and conversations like these?
Then it's time to upgrade to PRO:
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Welcome to Lead with AI, the only executive AI brief for busy leaders. Every Thursday, I deliver the latest AI updates through real-world insights and discussions from our community of 170+ forward-thinking executives.
For today:
- Entry-Level Jobs Are Vanishing: AI is erasing early-career roles—here’s what smart companies and future employees must do next.
- "AI for Dictation" Essentials: Wispr Flow and Granola AI
- 3 Must-Read AI Stories: ChatGPT Gains Enterprise Traction, AI Becomes Job Requirement, Fine-Tuning Turns AI into Your Edge
- Prompt of the Week: Make Tough Decisions with AI
Before we dive in, just a quick heads-up: Enrollment for my Lead with AI June cohort closes tonight at midnight. If you’ve been meaning to join but haven’t grabbed your spot yet, this is your last chance. Grab one of the few remaining seats with my special $199 OFF offer using this link!
LAST CHANCE: Sign up for June cohort
Let's dive in:
Practical Tips for the AI-Driven Workplace
Get real strategies AND implementation guides from business leaders delivered to your inbox every Tuesday.
AI Kills 50% of Entry-Level Jobs — So What Do We Do Now?

Anthropic CEO Dario Amodei caused commotion, at least in my corner of the internet, when he told Axios that “AI may wipe out 50 percent of entry-level white-collar roles within five years.”
Fresh data suggests he might be right:
- Big Tech graduate hiring is down by 50% since 2019 (SignalFire).
- Meta’s Mark Zuckerberg said AI will soon handle “mid-level engineer” work.
- ServiceNow agents already resolve 80% of support tickets unaided.
- An EY survey reveals that 48% of tech executives are deploying agent-based AI.
- Salesforce is redeploying 500 service reps into “data-plus-AI roles.”
Together, the signals point to a “broken bottom rung on the career ladder,” as LinkedIn’s Chief Economic Opportunity Officer, Aneesh Raman, wrote in The New York Times:
“In tech, advanced coding tools are creeping into the tasks of writing simple code and debugging — the ways junior developers gain experience. In law firms, junior paralegals and first-year associates who once cut their teeth on document review are handing weeks of work over to A.I. tools to complete in a matter of hours. And across retailers, A.I. chatbots and automated customer service tools are taking on duties once assigned to young associates.” – Aneesh Raman, Chief Economic Opportunity Officer, LinkedIn
So what does the entry-level job of the future look like, and how do we (workers and companies) get there?
Let’s dive in.
The New Entry-Level Job
I liked Josh Bersin’s counter to Amodei’s prediction that entry-level jobs are about learning and building a pipeline, not just cheap labor. And that cutting them creates long-term skill gaps.
This is something LinkedIn’s Aneesh Raman also highlighted: getting started later means less money and more inequality.
I’m also puzzled by what entry-level jobs are, anyway. Any first job that people (eventually) take is entry-level. How can they go away?
But yes, if we interpret those as the kind of roles Raman describes, I do think Amodei’s “50%” is directionally right. Jobs where you’re just copy-pasting, summarizing, or creating first drafts will become obsolete with AI.
However, in its place will be ‘first roles’ as ‘AI leaders' that young candidates are ideally suited for.
They enter the workforce as AI natives, and in fact, can teach today's leaders a lesson or two (reverse mentoring).
This is a place where graduates can actually have a significant advantage: Sam Altman recently remarked that younger AI users often tap it as a new kind of operating system, rather than a Google replacement.
These are the kind of people that employers are hungry for, as evidenced by Zapier CEO Wade Foster, who stated that 100% of new hires must be fluent in AI.

Because, as I recently stressed in my articles Prompt Engineering Isn’t Dead and You’re Only Using 10% of ChatGPT, AI still needs direction.
Today’s models are incredibly powerful. I’ve been working more with o3, and it amazes me what a reasoning model + tools can do. But no matter how impressive, they still need direction.
“The machine can do anything, now what do you want them to do?”
Tapping AI as a team member and prompting them well is key, alongside proficiency in tool fluency, to start or continue any career.
Even Amodei told Anderson Cooper so: the best hedge to future disruptions is simply “learn AI.”
That message is loudest for fresh graduates who now know what employers value:
- Baseline expectation: Do you know how to prompt, set up a simple assistant, and leverage different models? (See my new ChatGPT course if you need help.)
- Become a SuperWorker: Use my GED-RT framework (General, Error-friendly, Digital, Recurring, Toil) to identify tasks that AI (beyond ChatGPT) can handle today.
- Show real projects: custom GPTs, automations, and prompt libraries: proof you can tailor these models for real productivity and impact. (the stuff we do in the Lead with AI executive bootcamp.)
Do so, and graduates may even agree with PwC, which said they’re “lucky to be starting their careers as AI accelerates.”
Companies
But this discussion isn’t just about what people can do. It’s also a call to action for companies to get serious about AI at all levels:
- Name the risk in entry-level roles. As OpenAI writes in its playbook Identifying & Scaling AI Use Cases, jobs vanish only for people who never use AI.
- Recruit new team members who are AI-fluent, or at least (like I do), hire for the willingness, mindset, and attitude to work with AI.
- Encourage reverse mentoring. Sophie Wade said in an interview that “Many leaders are missing out on the contributions of their youngest employees who have a feeling for the power of technology that we just can’t have.” Tap into that.
- Upskill throughout. As OpenAI suggests, teach at least the six AI primitives (content, research, code, data, ideation, and automation).
- Get everyone building. Run a GED-RT sweep team-by-team to find low-joy, high-repeat tasks, and find quick wins just as Moderna went from 750 to 3,000 GPTs and J&J pruned 900 experiments down to the 15% that drove 80% of value.
SHRM Foundation Chair and Future of Work expert Edie Goldberg underscored the imperative for companies to rethink entry-level positions in exclusive commentary for this newsletter:
“Entry-level jobs are changing, but we need to rethink how people learn the business and build functional expertise. Research shows that AI is especially helpful for lower-performing employees—often those who are just starting out—because it provides access to the knowledge that drives success. Entry-level roles aren’t disappearing, but they are evolving. We need to evolve our thinking with them.” – Edie Goldberg, the Immediate Past Chair of the SHRM Foundation Board of Directors
Don’t Get Left Behind
The bottom line is that AI will eventually disrupt all jobs, and therefore, AI mastery is critical for everyone, from recent graduates to seasoned executives.
Students and graduates should prepare themselves to be as attractive in the market as possible by studying up on AI.
Companies should ensure they’re ready to hire those who are most likely to drive AI adoption and culture.
So, pick one GED-RT task this week, replace it with a prompt-plus-tool workflow, and demo the result—then repeat. The ladder may be shorter, but it climbs faster if we rebuild it now.