Hi! I'm Stephen Yang

Product Manager Pilot & Ground Instructor

I'm a Product Manager based in New York, with experience at Meta (Instagram), LinkedIn, and DocuSign. I focus on understanding user problems and creating solutions that make a meaningful difference. There's something rewarding about seeing a product evolve from concept to something people use daily.

I'm also the founder of Checkride, the AI operating system for flight schools, where I lead product and AI-assisted development across web and mobile.

Outside of work, I'm dedicated to aviation as a certified Pilot and Advanced Ground Instructor. I co-own a plane—N917LA—which gives me the freedom to explore from above. Flying offers a unique perspective and serves as a perfect counterbalance to my work in tech.

My Career Journey

A chronological overview of my professional experience, education, and achievements.

Founder

Checkride LLC • New York, NY

April 2024 - Present

Building Checkride (trycheckride.com), the AI operating system for flight schools. Leading product and AI-assisted development across web and mobile, including LLM-based training and fleet recommendations.

Senior Product Manager

Meta / Instagram • New York, NY

Dec 2025 - Aug 2026

Product lead for the consumer mobile upload experience across Reels, Feed, and Stories on iOS and Android.

Product Manager

LinkedIn • New York, NY

May 2024 - July 2025

Product Lead for Job Wrapping — a $2B line of business built on third-party ATS integrations — and 0-1 AI features within LinkedIn Recruiter.

Product Manager

DocuSign • San Francisco, CA

Sept 2021 - May 2024

Led product-led growth and eSignature partner integrations with Google, ServiceNow, Zoom, Microsoft Teams, and Slack. Promoted from APM.

Product / Technical Program Manager

Meta (formerly Facebook) • Menlo Park, CA

Feb 2020 - Sept 2021

Product Lead for the 0-1 Trust & Safety product area covering content moderation for businesses within Messenger conversations.

Internships

Meta • Databricks • Tesla • Medallia • California & New York

2016 - 2019

Completed multiple high-impact engineering and product internships at leading tech companies, delivering significant performance improvements and innovative solutions.

Pilot Experience

When I'm not building tech products, you'll find me in the skies. Here's a snapshot of my aviation journey as a Pilot and Advanced Ground Instructor.

PILOT LOGBOOK

Aug 9, 2026

PILOT LICENSE

Category:Airplane Single Engine Land

Issued:2021-08-04

Expires:No Expiration

GROUND INSTRUCTOR

Rating:Advanced

Issued:2024-02-22

Expires:No Expiration

LAST FLIGHT REVIEW

Apr 28, 2024

TOTAL TIME

94.7hours

PIC

46.1hours

DUAL RECEIVED

57.8hours

CROSS COUNTRY

17.6hours

TOTAL FLIGHTS

62flights

TAILWHEEL

8.3hours

AIRCRAFT EXPERIENCE

EVSS

55 flights83.9h

CH7A

5 flights8.3h

C162

2 flights2.5h

NOTABLE AIRPORTS

KRHVReid-Hillview

KLVKLivermore

E16San Martin

KWVIWatsonville

C83Byron

KTCYTracy

"Once you have tasted flight, you will forever walk the earth with your eyes turned skyward, for there you have been, and there you will always long to return." — Leonardo da Vinci