2026-08-25 21:04:15
👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Jobs | Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and my other favorite AI/PM courses
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Building on last week’s very exciting launch of Lenny’s Jobs (that’s a lot of likes!), I’m thrilled to bring you a companion post that will help you clarify what job to look for in the first place.
Cliff Maxwell teamed up with the legend Bobby Moesta (co-creator of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast) to build Vocation, a career navigation platform that helps professionals figure out their next step. Cliff’s own career has spanned building CPUs, education research, product management, venture capital, and serving as Chief of Staff to the late Clayton Christensen. Based on insights from over 1,000 interviews with professionals changing jobs and hundreds of one-on-one coaching clients, this hands-on guide will help you take a step back and connect with what you truly want from your work—and life.
Let’s get into it.
It’s a disorienting time to work in tech right now. For some, the rise of AI is a thrilling adventure, but for others, it’s a source of existential dread. No matter how you’re feeling, change is coming. The World Economic Forum reports that by 2030, 39% of today’s skills will change or become obsolete, and more than 90 million jobs will be displaced even as 170 million new jobs will be created.
Every generation of workers in tech has lived through recessions, layoffs, and technological change, but AI’s impact on work will be fundamentally different. It won’t just require new skills. It is redrawing the boundaries between roles and changing the day-to-day responsibilities inside them. Work may feel unstable now, but this will likely be the most stable it feels for a long time.
With this much uncertainty on the horizon, it is imperative that you develop the ability to navigate change. As your responsibilities shift and new opportunities emerge, the durable career advantage will come from knowing what kinds of problems, people, and environments bring out your best work—and having a repeatable process for identifying your next step even when the ultimate destination is unclear.
For the past year I have been building career navigation infrastructure with Bobby Moesta, one of the creators of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast. Bobby brings a product-oriented lens to career change: you are the customer, and the right next career move is the product you are looking to purchase.
Through more than 1,000 in-depth interviews with professionals changing jobs (some by choice, some by necessity)—and hundreds more people we have coached since—we identified what helps people make a successful job transition, and built a process to support them.
This is not a laundry list of LinkedIn hacks, resume tips, or ideas for how to automate your recruiting efforts. This is a step-by-step formula for designing a system that allows you to understand yourself, your context, and your best next steps when you’re in a state of change.
In this post, I’ll help you answer six fundamental questions that will instill confidence and focus anytime you are navigating a transition at work. Each question comes with exercises and tools to help you build understanding.
What kind of career progress do I want?
What career quest am I on?
Which work brings out my best?
What possible moves should I explore?
Which tradeoffs am I willing to make?
Can I get what I need without leaving?
Once you know your answers, you’ll be equipped to find your bearings now and every time the labor market throws you a curveball.
About a year ago, we coached an individual who, after spending several years at a startup that was running out of funding, assumed his next step was another early role in a venture-backed company.
After evaluating his core motivations and reflecting on his growing desire for impact, he found an opportunity to lead the entrepreneurship center at a local university, a job that he previously would have avoided and that none of his peers would have recommended. When he met with the administration, they effectively hired him on the spot, telling him, “You are exactly who we were looking for.” He’s now crushing it in his new role.
This story demonstrates the difference between career “progress” and “progression,” a distinction that is critical to understand when you are at a transition point in your career.
Progression is the philosophy that underpins most people’s mental model of careers. You start as an IC, get promoted, and up and up you go on the imaginary career ladder. This mindset will become increasingly less relevant as AI continues its march through knowledge work. Job boundaries and job titles will continue to blur, new job titles will emerge, and companies will struggle to neatly map job descriptions and career pathways into their org chart or KPIs.
Progress, on the other hand, is contextual and dynamic. It is ultimately a question of what your professional Job to Be Done is, and allows you to chart your own course rather than follow a single, narrow path of progression. Depending on your context, progress may be about autonomy and flexibility, preparing for the future, respect and recognition, or simply collecting a paycheck during a time of instability. It can look like a more traditional step up, but it may also look like a lateral move or even like a step back from the perspective of others—while it solves the most important problem in your life and gives you space and time to move forward later on.
A focus on progress is an active commitment to putting yourself in environments that will bring out your best. It helps you stand out amid the army of applicants all reaching for the same rung on the career ladder. Progress gives you the freedom to see your career in chapters and create space to be emergent rather than assuming you have to write one linear story all at once. To do this, you have to define the progress you’re seeking right now.
Take a blank page (or, if you’d like a live template, we made one for you here) and complete the sentence: I want to leave or change my current situation because…
Write down every friction or negative force you’re experiencing right now, or that you last experienced at work. We call these pushes. Do not polish the language. “My manager changes priorities every three days, and it’s getting exhausting” is more useful than “I want better leadership.” Unpack each one of these, and ask yourself “why” until you get to the root cause.
Then complete this sentence: I want my next chapter to give me…
List the desired outcomes you wish were true right now. We call these pulls. Again, make them concrete. “Control over when I do focused work” is more useful than “flexibility.”
Now circle the two or three pushes and two or three pulls that carry the most emotional weight. When you see the forces together, you can start to assemble what progress means for you, not for anyone else. For example, two people may both feel overburdened by new management, but one wants to join a more supportive team while the other is seeking more autonomy to work alone. Your unique combination of pushes and pulls forms the basis for your career quest, or the core motivation guiding your desire for change.
Below is an example of how this might look for someone seeking a new role:
When you are seriously considering a job change, or when change is forced upon you, it’s easy to label and hold onto your most immediate feeling, whether that’s burnout, the excitement of something new, frustration, or disrespect. But underlying these emotions, less-obvious and subconscious factors are working together in a unique combination to animate your core motivation for change. This is your career quest.
Your quest for progress should inform every aspect of your job search, but most people skip this diagnosis and go directly to job boards, answer the recruiter’s call, or ask their network about job openings. They are halfway out the door before deciding what they even need this move to accomplish.
For example, I once coached an individual who was frustrated by the lack of leadership opportunities in his product role at a large tech company. When he was recruited to lead and grow the analytics function at a nearby startup, he felt excited and flattered to finally have the opportunity to grow a team.
But as we explored other pushes and pulls acting on him, a more nuanced story emerged. Despite the lack of leadership opportunities, he fundamentally liked his job. He was also in the middle of renovating his home, he wanted to be able to spend more time with his two young kids, and he wasn’t all that excited about leaving product for analytics.
The new role solved his most immediate and apparent problem, but it wouldn’t offer him the progress he needed both personally and professionally.
In our work with professionals looking to make a change, we have identified four common quests for progress that emerge again and again.
These quests are not mutually exclusive; you can be on multiple quests simultaneously, though one usually dominates. Even if you have been laid off and the immediate goal is “I need a job,” reflecting on these quests can help you decide which opportunities deserve your attention, and which you can avoid.
You have hit a wall you cannot fix from where you stand. Something about the manager, culture, leadership, or environment has made it hard to succeed or remain healthy. The dominant feeling is escape, and the desire to get out is usually quick, not something you stew on for months at a time.
Common pushes:
Feeling disrespected or not trusted to do great work
Working for a manager who is wearing you down
Losing trust or respect in leadership and/or your peers
Not seeing a place to grow in your current organization
Common pulls:
The pulls are often vague: a fresh start, a healthier environment, or simply “anywhere but here.”
When someone is looking to get out, they often accept the first available escape but run the risk of landing in the same conditions at a different company.
Work has swallowed too much of your life, even if you still enjoy the work itself.
This quest often follows a change outside work: a new child, caregiving responsibilities, a health issue, or a shift in what you want your life to look like. It can also emerge when a previously manageable role becomes chaotic, or when the way your manager or company leadership is running things no longer works for you.
Common pushes:
Feeling worn down by management
Work is dominating your life and you’re starting to make sacrifices
Unpredictable demands, or feeling challenged beyond your ability
Little control over your schedule or priorities
A workload that no longer feels sustainable
Common pulls:
More time to spend with others
A job location that fits better into your personal life
An employer who properly values your experience and credentials
A scope of responsibility you can sustain
Your job has drifted away from what you do best, what you value, or what you originally agreed to do. You may still be performing well. In some cases, that is part of the problem: you have become useful for work that does not fit you, and you don’t feel respected.
Common pushes:
Being underused or miscast
Watching your responsibilities move away from your strengths
A growing gap between your values and the company’s
Feeling unchallenged or bored
Not seeing a clear place to grow inside the organization
Common pulls:
Work that uses your full capabilities
Greater alignment with your values
Recognition that matches your contribution
A role built around the things you do unusually well
You have completed something meaningful, mastered the role, or reached a point where the work no longer stretches you. Alternatively, you’ve hit a personal milestone (baby, move, etc.) and want a change. You are not necessarily unhappy. You are simply ready to be challenged and get the support you need to grow.
Common pushes:
Hitting a personal or professional milestone
Feeling unchallenged or bored
Not seeing a clear place to grow
Needing to provide more support for family or loved ones
Common pulls:
Feeling like a job is a clear step forward
Joining a tight-knit team you can count on
Developing new skills as part of a stepping stone to something else
Finish this sentence: More than anything, I need my next move to…
Get me away from a situation I can no longer tolerate.
Give me control over my time, workload, or life again.
Let me do work that fits my strengths and values.
Give me a new challenge or chapter.
How you finish the sentence will not capture every part of your situation, but it will usually reveal which quest you may be on—and also help you label what you don’t need right now.
Most professionals know their skills better than they know the conditions that allow them to do their best work. You take on responsibilities, become known for certain outcomes, develop valuable skills, but are often too busy doing the job to understand the circumstances you need to be successful and feel fulfilled.
Then a shiny title or compensation increase appears, and you accept a role that actually makes you miserable—an outcome common to ICs-turned-managers who realize too late how much they hate management.
You need to figure out what you need before you switch jobs (or are compelled to switch), not figure it out by switching. This is what building your energy profile is all about: it provides a blueprint for evaluating new opportunities, along with a starting point for questions you can ask a hiring manager or peer as you explore open roles.
To get started, grab some Post-it notes or spin up a Miro board, and make a simple timeline of roles you’ve held and the title, company, and duration for each role (including your current role if employed). If you want a pre-built template, we’ve got one here. The steps below will show you how to fill this out, and I’ve included an example of the beginnings of my own energy profile:
Pull up the past month of your work calendar and list what you actually did, hour by hour.
Do not use the language of your job description. Describe the activity:
Collaborative planning meeting
Individual research
Customer call
Writing a strategy document
To help you through this, you can integrate your calendar with an AI agent of your choice (via a simple connection or MCP) and use this simple prompt:
“For the past month, make a list of core meetings and time blocks on my calendar and ask me 1-2 questions about each to uncover what I actually did during those blocks of time. For example, if you see a ‘team meeting,’ ask me briefly what my role was and how I contributed. Then produce a list of the 8-10 core activities in my work life.”
Which tasks energized you?
Look for work where you lost track of time, volunteered extra effort, or kept thinking after the meeting ended. Include the tasks that left you with more energy afterward.
Which tasks did you avoid, postpone, rush through, or perform adequately just to get them over with?
Include work you are good at but dislike. Competence and energy are not the same thing. Many careers get built around things a person does well but does not want to keep doing.
Review your last job, then the one before that. You can’t go hour by hour, but for each role there were likely six to eight core responsibilities or tasks you engaged in on a regular basis.
As you complete this, you will begin to see a history of your career written in the language of energy instead of titles or responsibilities.
Revisit the activities you collected in the last step and see if you can identify broader themes or clusters that emerge from tasks that energize and drain you. As you do this, clarity is key. “Working with others” is not a clear theme. Neither is “heads-down work.” Working with whom? On what? Under which conditions? Similarly, “office politics” is not a clear theme for what drains you. What relationship dynamics are problematic? What decision-making processes don’t work for you?
To help you do this, you can ask questions like:
What is this more like?
What is this less like?
Which conditions need to be present?
Below is an example of unpacking a theme that emerged when I built my own energy profile: “environments that allow me to become an expert at the intersection of people and technology.”
As your themes begin to emerge, you’ll realize where you shine, where you check out, and what you want out of your next role. This is the foundational work necessary to begin prototyping potential opportunities.
2026-08-24 23:02:23
Listen now on YouTube • Spotify • Apple Podcasts
Brought to you by:
Bolt.new—Turn your idea into a real product
Jira AI SDLC—Get your tokens’ worth with Jira
In this solo episode, Claire tests Grok Bot, Cursor Origin, and Grok 4.6 to figure out what’s genuinely useful and what’s still mostly hype. She shares the Grok Bot feature that immediately won her over, why she isn’t ready to replace GitHub with Origin, and how Grok 4.6 performed against GPT-5.6, Claude Sonnet 5, and Opus 5 in her own blind evaluations.
Grok Bot’s multi-account connectors solve a problem every other agent platform seems to ignore. Most platforms assume each person has one Gmail account and one Slack workspace. Claire has four email addresses and seven Slack workspaces. Grok Bot lets her connect all of them to a single bot, which made it genuinely useful from day one in a way that Codex and Claude still have not matched.
Grok Bot’s simplicity is both its greatest strength and its biggest limitation. Setup is fast, the iMessage-style interface is clean, and the built-in plugins actually work. But people who enjoy customizing their agents, choosing models, shaping personalities, and tinkering with every detail may find it almost too polished. Claire loves her OpenClaw agents partly because they are chaotic and high-maintenance. So far, Grok Bot has not given her much to wrestle with.
Cursor Origin is a compelling vision that is not quite ready for prime time. An agent-native alternative to GitHub makes a lot of sense, especially one where Bugbot, Cursor, and the entire pull request workflow are designed around how coding agents actually work. Today, though, Origin still feels like a more attractive version of GitHub with fewer features. Teams that rely heavily on GitHub Actions, code owners, and existing automations will need a much stronger reason to migrate.
Grok 4.6 is a genuine frontier-model competitor. That conclusion did not come from someone else’s leaderboard. Claire runs her evaluations blind, grades the outputs herself, and gives her own judgment 70% of the final weight. Grok 4.6 finished alongside GPT-5.6 Sol at the top of the Claire Index, ahead of both Sonnet 5 and Opus 5.
For sharp, enjoyable agent conversations, Sonnet 5 is still the model to beat. When Claire wants an OpenClaw agent that is concise, responsive, and fun to talk with, Sonnet 5 continues to win. It has a conversational rhythm that feels more like working with a strong collaborator than issuing commands to a tool. Grok 4.6 does not yet compete in that category.
Cursor and xAI are assembling a surprisingly coherent enterprise stack. Grok Bot serves knowledge workers, Origin handles code hosting, Grok 4.6 provides a capable default model, and the Cursor IDE already sits at the center of many developers’ workflows. None of the pieces is perfect on its own, but together they are beginning to look like a credible enterprise platform. Large companies often prefer one vendor that can own the entire experience, and Cursor is increasingly positioned to become that vendor.
My Hands-On Review of GrokBot, Cursor Origin, and the Grok 4.6 Model: https://www.chatprd.ai/how-i-ai/how-i-ai-my-hands-on-review-of-grokbot-cursor-origin-and-the-grok-46-model
↳ How to Automate Knowledge Work Across Multiple Accounts with GrokBot: https://www.chatprd.ai/how-i-ai/workflows/how-to-automate-knowledge-work-across-multiple-accounts-with-grokbot
Listen now on YouTube • Spotify • Apple Podcasts
Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Jira AI SDLC—Get your tokens’ worth with Jira
Ryan Carson is a five-time founder and the solo founder of Untangle, a B2B SaaS platform for family law firms. In this episode, he breaks down how he manages up to 15 AI agents at once, ships as many as 40 pull requests a day, and uses Devin, Codex, and Claude Code to handle everything from engineering and QA to customer success and investor updates. He also shares why more AI output doesn’t necessarily lead to a better product, how a handwritten priority list keeps his agents focused, and why talking to one real customer changed the direction of his entire company.
The most important skill for a solo founder may be managing agents, not writing code. Ryan runs 10 to 15 Devin threads at once, organized into P0, P1, P2, and Bugs folders. He treats each thread the way a good manager treats a direct report: give it a clear goal, set the right priority, and avoid unnecessary hand-holding. That organizational discipline is what separates founders who gain real leverage from AI from those who simply accumulate open tabs.
A piece of paper can still be the best tool for protecting attention. Despite working across eight screens, Ryan keeps a handwritten list of his weekly priorities beside him. The simplicity is intentional. When agents are constantly generating updates, questions, and decisions, that physical list keeps him anchored to the three things that matter most before he gets pulled into whatever Devin surfaced overnight.
Ryan built an AI playbook that functions like a customer success team. His Watchdog workflow reviews every law firm account, pulls recent activity and errors from Sentry and internal logs, identifies the three most important problems, and checks whether a recent pull request has already fixed each one. Everything appears in a single Devin thread. Whenever Ryan feels the familiar anxiety of not knowing what is happening across his customer base, he runs Watchdog and quickly gets back up to speed.
Producing more with AI does not automatically lead to a better product. Both Ryan and Claire are skeptical of letting agents work without constraints overnight. Frontier models can generate an enormous amount of output, but they do not know what customers actually need. Product ideas, priorities, and market judgment still have to come from a human who talks to users. Ryan found product-market fit for Untangle not by shipping more code but by landing one meeting with family law attorney Renee Bauer and listening carefully.
Cloud agents may handle most engineering work, but Codex still shines when the frontend requires close attention. Ryan uses Devin for cloud-based work across bugs, pull requests, investor updates, and customer triage. He turns to Codex when a feature is visually complex and he needs to stay close to the implementation. The distinction is not about loyalty to a particular tool. It comes down to latency, browser access, and the ability to inspect and refine the interface in real time.
Coding agents can operate far beyond the codebase. Claire uses Devin for deal desk, custom quotes, and customer triage. Ryan uses it to prepare investor updates through a reusable skill. Both approach these agents with a broader question: What could someone accomplish if they understood the entire codebase and could write software to solve almost any problem? That framing reveals business uses that would never emerge from treating an agent as a simple coding assistant.
The best engineering interview may be a screen recording of the actual work. Ryan asks candidates to record themselves building a feature inside an existing application, with the entire screen visible and no introductory meeting required. In the next stage, he gives them access to Devin and reviews the replay of how they worked with it. This shows him how candidates think, build, and manage an agent under realistic conditions, which he finds far more revealing than a typical behavioral interview.
The strongest design workflow pairs Claude’s system thinking with Codex’s implementation ability. Claire used Claude Design to break a Figma file into reusable design tokens and a design.md specification. She then gave that specification to Codex, which created shared components across a monorepo. Claude is particularly good at translating a visual system into a portable spec. Codex is better at turning that spec into working, interconnected code. The workflow succeeds because each model is assigned the part it does best.
How Ryan Carson Manages 40 PRs a Day with Devin and Codex: https://www.chatprd.ai/how-i-ai/how-ryan-carson-manages-40-prs-a-day-with-devin-and-codex
↳ Create a Production-Ready Design System Using Claude and Codex: https://www.chatprd.ai/how-i-ai/workflows/create-a-production-ready-design-system-using-claude-and-codex
↳ Scale Code Quality with an Automated Land PR AI Workflow: https://www.chatprd.ai/how-i-ai/workflows/scale-code-quality-with-an-automated-land-pr-ai-workflow
↳ Automate Business Health Checks with a Watchdog AI Agent Playbook: https://www.chatprd.ai/how-i-ai/workflows/automate-business-health-checks-with-a-watchdog-ai-agent-playbook
If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.
Catch you next week,
Lenny
P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.
2026-08-24 20:04:02
Ryan Carson is a five-time founder and the current solo founder of Untangle, a B2B SaaS platform for family law firms. Before Untangle, he co-founded Treehouse, an online coding education platform, and has spent the better part of two decades building and leading tech companies. He’s active on X, where he shares his solo founder journey in real time, including what he actually spends on AI tools each month.
Listen or watch on YouTube, Spotify, or Apple Podcasts
Why Ryan manages 15 concurrent Devin agents with a folder system and a piece of paper, not a dashboard
The Watchdog playbook: what he built to replace a customer success team across every law firm account
How his LAN PR skill closes the loop on 40 daily PRs without a QA team reviewing a single one
Why he moved off local agents almost entirely, and the one situation where he still reaches for Codex
The design workflow we’re both using: Claude Design into a Markdown spec, then Codex to build the real thing
What he found when he got away from his computer and met a real customer, and why it changed his entire product direction
How he’s hiring his first engineer without a single phone screen or interview
Why we both think more AI output is actually the wrong goal, and what to optimize for instead
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Jira AI SDLC—Get your tokens’ worth with Jira
(00:00) Introduction to Ryan Carson
(02:55) Ryan’s update: Untangle, the divorce PMF pivot, and B2B growth
(07:35) Ryan’s current Devin stack: folders, P0 threads, and the paper list
(16:29) Watchdog playbook: account monitoring across every firm
(18:09) Managing agent decision fatigue: Ryan’s method vs. Claire’s
(20:32) Producing more output does not make a better product
(22:47) Using cloud agents for ops beyond just code
(25:14) When to use Codex vs. Devin vs. Claude Code
(27:15) Merge Mommy recap
(28:15) LAN PR skill: review loops, video walkthrough, and auto-merge
(30:20) Slack vs. Devin threads for async team communication
(35:58) Claude Design plus Codex for building a technical design system
(39:00) EA tools: Polly the OpenClaw vs. Claude Code on a Mac Mini
(42:09) Quick recap and final thoughts
• Devin (Cognition): https://www.cognition.ai/
• Codex (OpenAI): https://openai.com/codex
• Claude Code/Claude Design (Anthropic): https://www.anthropic.com/claude
• OpenClaw (Claude-based desktop client): https://openclaw.ai
• Cursor: https://www.cursor.com/
• BugBot (Devin’s built-in PR review): https://cursor.com/bugbot
• Sentry (error monitoring referenced in Watchdog): https://sentry.io/
• Ugmonk (analog to-do system): https://ugmonk.com/
• Devin playbooks/skills documentation: https://docs.cognition.ai/
• Jack Dorsey/Buzz (async-first communication referenced): https://buzz.new/
• Merge Mommy (Claire’s Eve agent for PR risk scoring, deployed on Vercel): https://www.lennysnewsletter.com/p/build-an-ai-code-review-bot-in-30
Untangle: https://untangle.us
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-08-23 20:31:43
Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15.
Listen on YouTube, Spotify, and Apple Podcasts
Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like
The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously
How to craft a two-to-three-sentence message around giving them “alpha”
How to run an intro call that extracts maximum intelligence before you ever show a demo
The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away
Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
• LinkedIn: https://www.linkedin.com/in/earlystagesales
• Website: https://www.jjellyfish.com
• State Affairs: https://stateaffairs.com
• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr
• SpaceX: https://www.spacex.com
• Lemlist: https://www.lemlist.com
• Palantir: https://www.palantir.com
• Jason Lemkin on X: https://x.com/jasonlk
• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents
• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org
• Careers at State Affairs: https://stateaffairs.com/careers
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
Lenny may be an investor in the companies discussed.
2026-08-23 03:23:07
👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.
2026-08-19 05:30:31
This week I’m doing a solo breakdown of everything xAI and Cursor have shipped recently, including Grok Bot, Cursor Origin, and the Grok 4.6 model. I set up five Grok Bots, ran Grok 4.6 through my Claire Weighted Index against GPT-5.6 Sol, Claude Sonnet 5, and Opus 5, and spent time actually using Origin as a GitHub replacement. Here’s what’s worth your attention, what’s overhyped, and where I’m personally putting my time.
Listen or watch on YouTube, Spotify, or Apple Podcasts
The one Grok Bot feature no other agent platform has shipped yet, and why it made me actually use the product
What a week of real Grok Bot use revealed, and why I still reach for my OpenClaws
Whether Cursor Origin is a GitHub replacement or just a pretty redesign
Where Grok 4.6 landed on the Claire Index, and the one category where it genuinely surprised me
Bolt.new—Turn your idea into a real product
Jira AI SDLC—Get your tokens’ worth with Jira
(00:00) Why everyone’s quietly switching to Grok
(01:52) Grok Bot overview and setup
(03:22) My 5 Grok Bots
(04:30) The killer feature: multi-account connectors
(06:07) Grok Bot’s virtual machine and how it actually works
(06:41) Experience overview
(07:35) What I don’t love about Grok Bot
(10:08) Grok Bot use cases and my honest verdict
(12:20) Cursor Origin: the agent-native GitHub replacement
(13:47) What Origin actually looks like in practice
(14:59) Why I’m not switching from GitHub yet
(17:42) What would get me to move over
(18:52) Grok 4.6 and the How I AI Vibe bench
(20:41) Claire Index results: where Grok 4.6 ranked
(23:03) Design evals: where Grok surprised me
(25:00) My conclusion and how I’m splitting my time now
• Grok Bot: https://x.ai/bot
• Cursor: https://cursor.com/home
• Cursor Origin: https://cursor.com/origin
• OpenClaw: https://openclaw.ai/
• GitHub: https://github.com
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
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