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Description
Embark on your journey to becoming a standout product manager with the Cool Package—a personalized coaching plan designed to elevate your application materials and execution skills. Whether you're aiming to break into product management or advance in your current role, this plan is tailored to help you craft compelling cover letters and hone your execution strategies. With a background in computer science from Brigham Young University and a master's degree from MIT, I bring a wealth of technical expertise and industry experience to our sessions. My professional journey includes roles at Amazon, where I integrated AI into Alexa's certification process, and at Nerd United, where I led efforts in building an NFT marketplace. Currently, as a software engineer at Leland, I contribute to the very platform you're using, ensuring it meets the highest standards of innovation and usability. Here's what we'll focus on together: Cover Letter Crafting: We'll work on creating cover letters that not only highlight your technical skills and achievements but also tell your unique story. I'll guide you in articulating your experiences in a way that resonates with hiring managers and sets you apart from other candidates. Execution Excellence: Product management is all about execution. I'll help you develop strategies to effectively manage projects, prioritize tasks, and deliver results. Drawing from my experience in software development and project management, I'll provide insights and techniques to enhance your execution capabilities. Throughout our sessions, I'll offer personalized feedback and actionable advice to ensure your materials and skills are polished and impactful. My goal is to empower you to confidently present yourself as a top candidate in the competitive field of product management. Let's work together to transform your aspirations into achievements and make your mark in the world of product management.
What you'll get from this package
Tailored cover letter that highlights your unique product management skills and experiences.
Additional details
Coaching delivered via live sessions.
Services included:
Execution
Cover Letters
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Jesse
Custom hourly · $150/hr
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Jesse also coaches for Career Coaching, Business Analytics & Intelligence, Life Coaching, and Mental Health & Wellness. View all.

Offered by Jesse H.
Joined October 2025
5.0
Launch&grow PM career | Ex-Amazon Product&Analytics Leader |Certified Coach
I’m a former Amazon Senior Technical Product Manager with 15+ years of cross-functional experience building data-driven products in advertising, analytics, and eCommerce. I’ve led products from concept to launch in complex, high-stakes environments, working across engineering, data science, UX, analytics, and business leadership. My background also spans IBM consulting, Ipsos research, and Ogilvy marketing, giving me a uniquely holistic perspective on both product strategy and customer insight. I coach both professionals who want to pivot into product management for the first time, and product managers who want to advance to the next level. My coaching integrates hands-on product expertise with leadership and mindset development (ICF-certified coach), helping you not just learn the “mechanics” of PM, but also gain the confidence, executive presence, and clarity that drive long-term success.
$2,000
10h of coaching