Jovan Postoloski
Lead AI Evaluation & Alignment Specialist | Full-Cycle (0→1) Eval Design & Production Deployment | RLHF · LLM-as-Judge · RAG Governance | Dropbox Dash AI · xAI (FTE) · Google · Meta
Crown Point, Indiana, United States
Career path.
- Dropbox
Lead AI Evaluation & Alignment Specialist - Dash AI
Feb 2026 - Present - Self-employed
Technical Governance & AI Strategy | Independent Consultant
Nov 2025 - Feb 2026 
xAIModel Behavior & Logic Integrity Auditor, Grok Alignment Team - AI Tutor (Direct Hire/FTE)
Nov 2024 - Nov 2025- xAI
AI Tutor
Nov 2024 - Nov 2025 - Google
AI Response Design & Evaluation Specialist (Google AI Overviews(SGE)/Gemini)
May 2023 - Oct 2024 - Tech Mahindra
Google AI Content Specialist
May 2023 - Oct 2024 - Morrison Urena, L.C.
Senior Paralegal & Team Lead
May 2021 - Oct 2022 - Morrison Urena, L.C.
Senior Paralegal & Operations Lead
May 2021 - Oct 2022 - Morrison Urena, L.C.
Paralegal
Apr 2021 - May 2021 - The Worldwide Times
Content Specialist
Jun 2020 - Apr 2023 - Pikasa Analytics
Technical Writer & Data Analyst (SaaS Startup)
Feb 2020 - Mar 2021 - 360 Stepeni
Social Media Manager
Mar 2017 - Oct 2020 - SDUM (one of Macedonia's top political parties) - National campaign for parliamentary election
Communications Specialist & Speechwriter
Sep 2016 - Jun 2017 - TV Show "Counter News" ("Kontra Vesti")
Script Writer
Nov 2015 - Jan 2016 - Satirical news website http://www.kozanostra.net/
Web Content Writer
Sep 2014 - Sep 2016 - News Website "Libertas" (http://www.libertas.mk)
Co-founder & Content Director
Dec 2012 - Apr 2021 - Political weekly magazine "Focus" ("Fokus")
Script Writer (Political Comics)
Jul 2011 - Dec 2013 - A1 Television
TV Host, Writer & Creator
Jul 2010 - Jul 2011 - Daily newspaper "Strike" ("Spic")
Columnist
Mar 2010 - Jul 2011 - Daily newspaper "Daily" ("Dnevnik")
Journalist
Jun 2009 - Aug 2009 - Political weekly magazine "Now" ("Sega")
Journalist & Columnist
May 2009 - Mar 2010 - MX Radio
Radio Host & Audio Producer
Aug 2004 - Sep 2008