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Here's your package description — copy and paste ready: You're already in the role. Now the question is: how do you become the PM everyone wants on their hardest problems? I spent four years at Intuit building and scaling Customer Agent — the company's first agentic AI product — from a blank page to 6 million small businesses across 170 countries. The CEO called it "the most significant launch in our history" in Fortune. Before that, I led product at Workday Financials and spent years in quantitative finance at Morgan Stanley and Franklin Templeton. I've been in the room making the calls you're navigating right now. This package is for AI PMs (or PMs moving into AI) who want ongoing, high-context coaching from someone who's operated at the highest level of the function. Not interview prep — real career acceleration. What we'll work on together: → Roadmap & strategy: How to build conviction around what to ship, how to sequence bets, and how to defend your roadmap to leadership when the landscape shifts every quarter. → Stakeholder & executive communication: Framing AI product decisions for non-technical execs, managing up effectively, and building the kind of trust that gets you pulled into the most important rooms. → Navigating ambiguity in AI: Model uncertainty, hallucination tradeoffs, build-vs-buy, agent architecture decisions — the messy reality of shipping AI products that no framework fully captures. → Career trajectory & positioning: Whether you're trying to move from IC to lead, get the Staff/Principal title, or figure out your next move — I'll help you think through it with the same rigor I'd apply to my own career. → Team building & hiring: How to identify, interview, and develop strong AI PMs on your team, and how to structure an AI PM org that actually works. → Financial literacy for tech careers: As a CFA charterholder, I bring a lens most PM coaches can't — RSU strategy, comp negotiation, how to think about your career in financial terms so you're not just earning well but building wealth. Each session is tailored to whatever is most urgent for you. No generic templates. No recycled frameworks. Just direct, experienced counsel from someone who's done the job at scale.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
The plan focuses on real career acceleration rather than interview preparation, offering high-context coaching tailored to individual needs.
Key areas of focus include roadmap and strategy development, stakeholder and executive communication, navigating AI ambiguity, career trajectory, team building, and financial literacy.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
Key areas of focus include roadmap and strategy development, stakeholder and executive communication, navigating AI ambiguity, career trajectory, team building, and financial literacy.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
The coaching plan is designed for AI Product Managers seeking to enhance their strategic, leadership, and execution skills in AI product management.
Coaching delivered via live sessions and .
I coach the way I like to be coached — direct, no fluff, focused on whatever's actually blocking you right now. Every session starts with what's on your mind. A gnarly stakeholder situation, a career-level decision, a promotion case, a reorg pitch — I don't show up with a predetermined curriculum. I show up ready to go wherever the conversation needs to go. I'll push back when I think you're wrong and tell you when you're underselling yourself. The goal is to leave every session with clarity you didn't walk in with. What sets me apart: I've done the job. I built and scaled an AI product from zero to millions of users at a $170B public company. When you describe a situation, I've probably been in a version of it. That makes the advice sharper than what you'll get from a generalist coach. Between sessions, I'm available async for quick gut-checks — a second opinion on a tough email, a read on a promotion case, a sanity check before a big meeting. You're not just buying an hour — you're getting an experienced operator in your corner.
Expected Response Time within 24 hours!
Services included:
AI Fundamentals
AI Ethics & Responsible AI
Prompt Engineering
AI Graphics Creation
AI Agents
AI Automation
AI Research
AI Tools & Integration
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
3h of coaching