Leland+ for Break Into AI Careers

The 2026 AI Strategy Playbook

A strategy session for ambitious professionals who want to stand out so clearly in the AI era that leadership can’t ignore them.

AI Monthly News Update - January 2026 (Slides)

These slides are from the first of a series of monthly news updates related to advancements in AI. This update covers AI tools and LLMs, global AI and infrastructure, robotics and gadgets, and the impact of these advancements on daily life and business. Check out the event here: https://www.joinleland.com/content/item/urn:contentEntry:69839327a1f4968d5ca1feb5?fromName=all

Career Pathways in Trust and AI Safety

Trust and AI safety roles are growing quickly, but the paths into them are often unclear and highly interdisciplinary. This session is for students and professionals who want to understand how to break into this space and what backgrounds actually translate. You’ll learn how to map your current experience to relevant roles, identify the core skills and knowledge areas that matter, and position your interest in AI safety in a credible, differentiated way.

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.

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.

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.

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.

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.

October Series Session 7: Negotiating Confidently

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

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.

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.

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.

AI Week Kickoff: AI’s Impact on Jobs, Business, and Daily Life

Join us as we kick off AI Week with an incredible panel exploring how artificial intelligence is reshaping the ways we live and work. This session, AI’s Impact on Jobs, Business, and Daily Life, brings together leading voices at the intersection of technology, work, and innovation — Andrew Q. (former Head of AI at Spotify, early OpenAI Engineer), Andrew S. (Editor at Large for Jobs & Career Development at LinkedIn News, Host of the Get Hired podcast), and Solomon C. (AI and Automation Expert). Together, they’ll unpack how AI is transforming industries, redefining roles, and creating new opportunities for both individuals and organizations. ​The kickoff is just the start. Throughout AI Week (Nov 10–13), we’ll dive deeper into the most important ways AI is shaping our world — from practical sessions on AI upskilling and using AI to grow your business, to insights on building a career in the age of AI. Whether you’re a professional, student, or business owner, you’ll leave equipped with the tools, strategies, and inspiration to thrive in the AI era.

How to Land a Job as an AI Product Manager

AI product management is one of the most exciting and fast-evolving roles in tech—but it can also be one of the hardest to break into. In this panel, Jeff N. (Principal PM @ Amazon), Nina O. (Former Lead PM @ Google), and Sonya K. (Former PM @ Microsoft) will share what it takes to land a PM role in the age of artificial intelligence, from building technical fluency to showcasing strategic thinking and cross-functional leadership. ​You’ll learn how top candidates position themselves for success, what hiring managers at companies like Meta, Google, and OpenAI are looking for, and how to stand out even without a traditional AI or engineering background. Whether you’re an aspiring PM or looking to transition into AI-focused products, this session will give you actionable insights and a clear roadmap to your next big opportunity.

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.

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.

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.

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.

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.