Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
A tailored, outcome-focused coaching plan built around your specific background, target roles, and timeline — so every hour you spend preparing is spent on the right things, in the right order. Here's what we'll work through together: - Personalized prep roadmap — A clear, ROI-driven plan for how to spend your time most effectively: what to focus on, in what order, and why - Resume & LinkedIn positioning — Review and guided revision to sharpen your narrative and increase interview traction, plus outreach templates that improve response rates - Application & targeting strategy — A focused approach to finding and prioritizing the right roles, including how to leverage your unique background to stand out at your target companies - PM interview frameworks — Proven frameworks for all major PM interview question types (product sense, execution, strategy, behavioral), so you prepare efficiently rather than passively watching mock videos - Interview pattern analysis — Deeper synthesis of what interviewers are actually looking for, with practical guidance to improve your conversion rate - AI-powered job search tools — Hands-on guidance on using AI tools to streamline your search and prep — skills you'll keep using long after this job hunt - Anything else you need — Sessions are flexible and built around you
A revised resume and LinkedIn profile with sharper PM positioning - built to 10X increase your hear-back rate
Introductions and referrals to relevant contacts at target companies where I have connections
The PM Interview Accelerator plan is a personalized coaching program designed to optimize preparation for product management roles by focusing on individual backgrounds, target roles, and timelines.
A personalized prep roadmap with prioritized focus areas, frameworks, and an application strategy tailored to your background and target roles
Participants receive guidance on refining their resumes and LinkedIn profiles to enhance their professional narrative and improve interview response rates.
The plan offers a targeted application strategy to help candidates identify and prioritize roles that align with their unique backgrounds and strengths.
Proven PM interview frameworks are provided to prepare candidates for various question types, promoting active learning over passive observation.
Interview pattern analysis is included to help candidates understand interviewer expectations and improve their interview conversion rates.
The plan incorporates AI-powered job search tools to streamline the job search process and enhance preparation efficiency.
Sessions are flexible and tailored to individual needs, allowing for personalized support throughout the coaching process.
The coaching plan emphasizes authentic storytelling and strategic positioning to help candidates stand out in the competitive product management field.
Coach Ollie brings extensive experience from leading product roles at Amazon and Asana, offering practical insights and frameworks developed through personal career transitions.
Coaching delivered via live sessions and .
My coaching style is direct, practical, and tailored to you - no generic advice or one-size-fits-all frameworks. We start by diagnosing exactly where you are and what's blocking you, then build a focused plan from there. Live sessions are used for high-leverage work: strategy, frameworks, mock interviews, and real-time feedback. Between sessions, I'm available async for resume reviews, quick questions, and accountability check-ins, so momentum doesn't stop when we're not on a call. I bring a practitioner's perspective as a current Product Owner at Asana with a background in engineering and AI, so the guidance is grounded in what actually works in today's market.
Services included:
Skill Building
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
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Get help with Cover Letters, General Exploration, and .

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.
3h of coaching