AS

Alex Schiff

Product at Headway

New York City Metropolitan Area · 1 connection

Headway

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About

I’ve been a founder, startup GM, first/early PM hire, and staff PM at a public company. My best work usually comes from working with a high-agency team on emerging tech, and my happiest days are when I get to see the impact with real customers. Over the course of my career, I've worked on products related to 3D mapping (SLAM), home improvement, AR/VR, LLMs, productivity and collaboration, media, customer support, small business, and all kinds of internal tools. Now I’m working on using AI to improve the quality and consistency of mental health care at Headway. Tech-wise, I've built random things with JavaScript, HTML, CSS, Lua, Webscript, Twilio's API, FullContact's API, and Parse. I’ve also built a handful of custom GPTs — ask me about Lazy Wellness! Occasionally, I think out loud on Medium:

Experience

Staff Product Manager, Network QualityHeadway Basic company page — company details not listed yet
Jan 2026
Staff Product Manager, Square AISquare
May 2024 to Dec 2025
Product LeadSquare
Nov 2022 to May 2024
Product ManagerSquare
Nov 2021 to Nov 2022
VP Product, Outputs & OperationsOccipital Basic company page — company details not listed yet
Jan 2020 to Nov 2021
Editorial and Business DevelopmentBenzinga Basic company page — company details not listed yet
May 2010 to May 2011
Assistant Editor and ColumnistThe Michigan Daily Basic company page — company details not listed yet
Jan 2010 to May 2010

Education

Techstars (Boston, Class of Fall 2012)
2012 to 2012
University of Michigan - Stephen M. Ross School of Business
Bachelor of Business Administration (B.B.A.) Business Entrepreneurship Finance
2010 to 2012
Palm Harbor University High School
High School Diploma International Baccalaureate
2006 to 2009
North Farmington High School
High School
2005 to 2006