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Description
This package is designed for aspiring and experienced Product Managers targeting PM, Technical PM, and AI PM roles at MAANGO, leading tech companies, and high-growth startups. Whether you are transitioning from engineering or another function, moving into AI product management, or preparing for your next PM role, we’ll build a personalized strategy around your background, target companies, and biggest gaps. ### 1. Career Strategy & Positioning We’ll start by evaluating your experience, strengths, and target roles. Together, we’ll: * Identify the PM and AI PM roles that best match your background * Clarify your professional narrative and key differentiators * Identify experience or skill gaps that may be holding you back * Build a focused, realistic job-search and preparation plan ### 2. ATS-Optimized Resume We’ll transform your resume from a list of responsibilities into a strong PM story that demonstrates impact, leadership, decision-making, and end-to-end ownership. This includes: * Detailed resume review and targeted revisions * Stronger, metrics-driven bullet points * Clear positioning for PM and AI PM opportunities * Relevant product, technical, and AI keywords for ATS screening * Guidance on creating separate general PM and AI-focused resume versions when helpful ### 3. Application Strategy You’ll learn how to run a more focused and repeatable application process, including: * Prioritizing companies and roles * Tailoring your resume efficiently * Building a consistent application pipeline * Using referrals, networking, and recruiter outreach * Tracking applications and improving your strategy based on results ### 4. PM & AI PM Interview Preparation We’ll prepare for the interview areas most relevant to your target roles: * “Tell me about yourself” and “Why PM/AI PM?” * Behavioral and leadership interviews * Product sense and product design * Execution, prioritization, and metrics * Product strategy and go-to-market questions * Technical and AI product discussions * AI use cases, model tradeoffs, evaluation, data, cost, latency, trust, and responsible AI ### 5. Mock Interviews & Personalized Feedback You’ll practice in realistic mock interviews and receive direct, actionable feedback on: * Answer structure and clarity * Product judgment and analytical depth * Executive communication * Areas that need additional practice * How to make your answers more concise, credible, and memorable ### Resources Included Depending on your goals, you’ll receive: * Sample PM and AI PM resumes * Resume revision examples * PM interview frameworks and answer templates * Behavioral story-building guidance * Interview question banks * Application strategies and tracking resources * Personalized session notes and next steps By the end of the package, you’ll have a clearer career narrative, stronger application materials, a repeatable job-search strategy, and a structured system for approaching PM and AI PM interviews with greater confidence.
What you'll get from this package
A personalized strategy for targeting the right PM, Technical PM, and AI PM roles
A fully revised, ATS-optimized resume that clearly communicates product impact, leadership, and technical expertise
A stronger career narrative, elevator pitch, and behavioral story bank
A repeatable application system covering role prioritization, resume tailoring, referrals, and outreach
Practical frameworks for product sense, execution, strategy, metrics, and AI product interviews
Realistic mock interview practice with direct, actionable feedback
A personalized improvement plan identifying strengths, gaps, and next steps
A separate AI-focused resume version when relevant
Reusable templates, examples, interview resources, and session notes
Additional details
Coaching delivered via live sessions and .
Services included:
LinkedIn Review
Execution
Promotion Strategy
Cover Letters
Resume Review
Networking Strategy
Freelancing
Strategy & Vision
Salary Negotiation
Influence & Collaboration
Product Case Interview Prep
Frameworks
Behavioral Interview Prep
General Exploration
AI Fundamentals
AI Agents
AI Automation
Prototyping with AI
User Research & Insights Automation
AI Product Design
Skill Building
AI Roadmap Development
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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Offered by Ollie G.
Joined April 2025
5.0
Break into PM with Tech Background | USC Alum, ex-Amazon
Hey I’m Ollie! and I’ve been exactly where you are. I’ve navigated countless applications, refined my resume dozens of times, and pushed through burnout and self-doubt while trying to break into (or level up in) Product Management. My journey started as a product manager — leading product at an edtech startup, then working on technical product initiatives at Amazon — before landing my current role at Asana, where I build GenAI products. After hundreds of interviews and the rollercoaster of rejections and breakthroughs, I developed a practical framework to help you play to your strengths, tell your story with confidence, and land the role that truly fits you. My coaching goes beyond templates. I’ll help you clarify & customize your story, amplify your advantages, and stand out authentically in the competitive world of PM. I’m passionate about helping aspiring and transitioning product managers navigate their career paths, from resume building and interview prep to mindset rebuilding and strategic positioning. Let’s connect and create a personalized plan to help you stand out and succeed in the competitive world of product management.
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