Gaylan G.

Gaylan G.

⚡️ Helping people break into product management and grow their skills

United States Naval Academy Logo

Studied at United States Naval Academy

Airspeed Logo

Worked at Airspeed

Available Wednesday at 12:00 AM UTC

Questions? Start chatting with this coach before you get started.

Gaylan's Coaching Offerings

Custom hourly · $69/hr

Get help with Skill Building, LinkedIn Review, and .

Gaylan’s Product Management Qualifications

Experience level: Product Manager

With a robust background in product management and a proven track record of success in high-stakes environments, I am uniquely qualified to serve as a Product Manager Coach. Having conducted over 50 full-loop PM interviews and secured more than 20 job offers across leading tech companies, I bring deep expertise in navigating the complexities of the PM hiring process. My extensive experience spans SaaS, consumer products, and AI-driven solutions, complemented by over five years in product management roles at companies like Amazon, LinkedIn, Guideline and now defense tech at Overland AI. This diverse portfolio equips me to guide aspiring PMs through crafting compelling narratives, mastering behavioral and technical interviews, and aligning their skills with industry expectations. My coaching approach is informed by a strategic blend of leadership, mentorship, and hands-on product management experience, including my 11 years as a Naval Officer, where I honed skills in high-pressure decision-making and cross-functional collaboration. I am passionate about empowering others to break into product management and grow their PM skillsets, leveraging my insights from iterating on customer activation funnels, building delightful user experiences, and driving strategic outcomes at scale. I am committed to helping people achieve their PM career goals with confidence and clarity.

Gaylan can help with:

Skill Building

LinkedIn Review

Execution

Resume Review

Networking Strategy

Strategy & Vision

Influence & Collaboration

Product Case Interview Prep

Frameworks

Behavioral Interview Prep

General Exploration

View all of Gaylan’s categories

About Gaylan

🦄 Senior Product Manager at Overland AI building autonomous off road vehicles for the department of defense, allies, and national security adjacent organizations. Responsible for command and control interface, hardware (vehicle and payloads), and autonomy stack. 🌟 Former Product Manager at LinkedIn, Amazon, Guideline (Series E - recently acquired by Gusto), and Airspeed (Series Seed Start up) ⚓️ Veteran Naval Officer with 11 years of leadership experience leading teams from 30 to 100 throughout 4 operational deployments. Former U.S. Navy-Senate Liaison working at the Navy Office of Legislative Affairs and Flag Aide (Deputy Chief of Staff) to the Chief of Legislative Affairs for the Navy. ⚽️ Former Division I and Professional Soccer Player ❓Ask me about: ⦿ Military and First Responder Veterans transitioning to tech industry ⦿ Breaking into Product management ⦿ B2B SaaS and Defense Tech ⦿ Chief of Staff and executive stakeholder management ⦿ Creating/implementing organizational and team systems and mechanisms that scale

Work Experience

Overland AI Logo

Senior Product Manager

Overland AI

July 2025 - Present

Responsible for the hardware (ULTRA), command and control interface (OverWatch), and our autonomy stack (OverDrive) working with 39 engineers building autonomous off road vehicles for the department of defense and national security adjacent customers.

simpler. Logo

Product Advisor

simpler.

September 2022 - Present

Amazon Logo

Senior Product Manager

Amazon

March 2025 - July 2025

Responsible for Kindle Unlimited selection strategy across 14 countries world wide as well as the Product Owner for the Amazon Prime Reading benefit world wide.

Guideline Logo

Senior Product Manager

Guideline

February 2024 - February 2025

Led an engineering and design team of 12 responsible for the participant (employee) and sponsor (admin) experiences including web and mobile apps.

Airspeed Logo

Senior Product Manager

Airspeed

June 2021 - October 2023

U.S. Navy Logo

Senior Director of Plans and Strategy

U.S. Navy

January 2021 - May 2022

U.S. Navy Logo

Director of Operations

U.S. Navy

November 2019 - December 2019

LinkedIn Logo

Product Manager

LinkedIn

August 2017 - September 2018

Responsible for the LinkedIn Sales Navigator Core Experience.

U.S. Navy Logo

Deputy Chief of Staff to the Chief of Legislative Affairs

U.S. Navy

October 2016 - August 2017

U.S. Navy Logo

U.S Navy-Senate Liaison

U.S. Navy

May 2015 - October 2016

U.S. Navy Logo

Head of Antiterrorism

U.S. Navy

January 2014 - May 2015

U.S. Navy Logo

Head of Main Propulsion Division

U.S. Navy

July 2011 - December 2013

Gaylan was also given offers to work at

  • Dropbox Logo

    Dropbox

  • Anduril Industries Logo

    Anduril Industries

  • Havoc AI Logo

    Havoc AI

Education

United States Naval Academy Logo

United States Naval Academy

Bachelors, Quantitative Economics

2007 - 2011

The mission of the US Naval Academy is to develop Midshipmen morally, mentally and physically and to imbue them with the highest ideals of duty, honor and loyalty in order to graduate leaders who are dedicated to a career of naval service and have potential for future development in mind and character, to assume the highest responsibilities of command, citizenship and government.

Gaylan G.

Gaylan G.

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