Leland+ for Break Into AI Careers

How to Land a Job in the New Frontier: AI Careers

AI is reshaping every industry, and landing a role in this fast-moving space requires more than just technical interest. This session breaks down the AI job landscape, the roles companies are hiring for, and how candidates from technical and non-technical backgrounds can position themselves competitively. You’ll learn how to build relevant skills, craft a compelling narrative, and navigate recruiting for AI-focused roles across tech, startups, and traditional companies.

Home for Ambition #2 — Weekly Live Show [3/25/2026] (Recording)

Home for Ambition is a weekly live show, by Leland, for people trying to stay ahead as work, learning, and opportunity keep changing. Each episode tackles a handful of timely, high-signal topics across AI, careers, education, and the future of work. We expect thoughtful debate, unique perspectives, and practical takeaways you can actually use. It is not a typical interview show or a generic news recap. It is a live roundtable built to help ambitious people make sense of what is changing, understand what matters, and leave with a sharper point of view on how to navigate what comes next.

How to Transition Into AI from Any Background

Many professionals are interested in working in AI but aren’t sure how to translate their current skills into opportunities in the field. This session is designed for candidates from technical and non-technical backgrounds who want a realistic path to entering the AI ecosystem. You’ll learn how to identify transferable skills, position your experience for AI-related roles, and prioritize the tools, projects, or learning paths that hiring managers actually value.

OpenClaw for Beginners: Build AI Agents from Scratch (Free)

A complete beginner-friendly course on building and running AI agents using OpenClaw Architecture — 100% free to set up. In this course, you'll learn how to: • Install and configure OpenClaw on a DigitalOcean droplet (cloud server) • Connect your preferred language model (OpenAI, Claude, Gemini, Grok, Qwen, and more) • Understand the core anatomy of an AI agent: soul, identity, skills, memory, heartbeat, and cron jobs • Add Perplexity-powered search capability to your agent • Troubleshoot terminal errors in real time using a "fail fast" methodology • Manage costs and token usage to keep your monthly spend under $50 • Think like a builder: define your success outcome before writing a single line of config This course is built for non-technical beginners and power users alike. You'll watch a live, detailed setup — including real errors and how to fix them — so you know exactly what to expect when building your own agent infrastructure. By the end, you'll have a self-hosted AI agent running autonomously in the background, capable of handling research, sales outreach, content, and more — amplified across everything you do.

Breaking into AI with a Non-Technical Background [5/6/2026] (Recording)

Breaking into AI can feel out of reach if you don’t come from a technical background, but there are more accessible paths than most people realize. This session is for professionals looking to transition into AI without coding-heavy experience. You’ll learn how to position your existing skills, identify entry points across roles, and build practical experience that signals capability in an AI-driven landscape. Join live to ask questions about your own background and get guidance on how to make the transition. The speaker works with individuals navigating career pivots into AI and will share the patterns they see across those who successfully break in. Expect practical advice and insights similar to what’s discussed in 1:1 coaching conversations.

Introduction to the AI Company Landscape & Assignment

This will introduce the AI jobs landscape and also share reading to help you dive deeper to understand the entire AI market. There is an assignment to research three companies of interest to better understand what companies in this space do.

Walk through of AI Company Landscape with Live Examples

In this live guided walkthrough, we'll walk through Bessemer's AI market map to understand the entire landscape of how these AI companies operate together, and talk about different considerations in taking jobs in different parts of the AI stack.

October Series Session 7: Negotiating Confidently

This session teaches you to treat salary negotiation as a normal business conversation about your value.

From Applicant to AI Marketer: Your Blueprint for Landing a Dream Job

Landing your dream job at the intersection of AI and marketing demands more than just a sharp resume—it requires strategic positioning, domain fluency, and an ability to tell your story through data. Join Arthur B., seasoned product marketing leader with experience at Meta, TikTok, Adobe, and now Google AI, to get the inside scoop on what it really takes to break into the AI marketing world. ​Arthur will walk you through how to identify and build the right skills, tailor your narrative for AI-driven roles, and structure your application to land attention in a crowded field. ​Whether you’re pivoting from a traditional marketing role or entering the AI space for the first time, this session will give you a clear blueprint to differentiate yourself and move confidently toward your ideal role.

Forward-Deployed Engineers & AI Services-Led Growth

Explores the FDE role in detail: client-facing integration, technical implementation, rapid prototyping, and serving as a bridge between engineering and GTM, supported by insights from a16z and industry examples. Assignment encourages role research and personal reflection.

Introduction to Roles in AI — How It Differs from Traditional Tech

This reading introduces you to key roles like research engineer, forward deployed engineers, and different GTM jobs at AI companies. It includes an assignment designed to teach you how to better understand these roles.

Which AI job is the right fit for me?

Reading to understand roles and impact on things like work-life balance, focus time vs. meetings, and more. Includes a research assignment and table laying out different aspects of each job.

Understanding AI Compensation Data 2025

Provides updated, accurate AI salary ranges across roles such as AI researcher, MLE, and FDE, based on Glassdoor, Levels.fyi, and recent industry reports including the NYT's superstar compensation story. Includes assignment to benchmark target roles against market pay.

Mastering AI Networking & Referrals

Guide to building meaningful relationships in the AI ecosystem, overcoming hiring noise, and securing referrals through thoughtful engagement and value-add interactions.

Inside the Forward-Deployed Engineer Role

Interactive session dissecting the FDE role with real-world examples, skill mapping, and discussion on how FDEs accelerate AI adoption in enterprise environments.

Creating Impactful Pre-Job Projects

Walkthrough of building and presenting portfolio pieces that resonate with AI employers, featuring tips on storytelling, technical demonstration, and networking through project sharing.

AI Job Market Noise, Networking Strategies & Referrals

Examines challenges posed by imprecise AI job listings and teaches targeted networking practices, referral system insights, and rapport-building with insiders, plus an assignment to initiate connections and refine messaging.

Navigating AI Salary Data & Market Trends

Walkthrough of key salary datasets and trends, explaining what drives compensation differences and how candidates can evaluate offers and align career goals with compensation realities.

Building Your AI Portfolio & Outside-In Projects

Detailed strategies for engineers, designers, marketers, and data scientists to craft projects showing value aligned with target companies. Includes best practices for packaging and sharing work and an action-oriented assignment.

Finally Use AI for Something Useful: Build AI Literacy That Moves Your Career Forward

AI is everywhere—but understanding how to use it effectively for your career can feel overwhelming. In this session, AI expert Matthew W. (Stanford, Meta) will guide you through practical ways to build AI literacy and leverage AI tools to enhance your work, decision-making, and professional growth. ​You’ll learn how to identify meaningful applications of AI in your role, avoid common pitfalls, and use AI strategically to save time, boost productivity, and strengthen your skillset. By the end, you’ll walk away with actionable strategies to move your career forward with confidence in an AI-driven world.