Meet SkillSail AI at San Antonio Startup + Tech Week · September 28–October 2, 2026.

SkillSail
Home
Why SkillSail.ai
Privacy & Trust
About
Investors
Join Beta
SkillSail
Home
Why SkillSail.ai
Privacy & Trust
About
Investors
Join Beta
More
  • Home
  • Why SkillSail.ai
  • Privacy & Trust
  • About
  • Investors
  • Join Beta
  • Home
  • Why SkillSail.ai
  • Privacy & Trust
  • About
  • Investors
  • Join Beta

About Us

Man in a blue Microsoft shirt smiling outdoors.

Chris Osterhaug, Founder & CEO

Chris Osterhaug, Founder & CEO

Chris Osterhaug, Founder & CEO

 

Building SkillSail.ai to make hiring smarter and privacy-first.


Bio:  

Veteran technologist, relentless problem-solver, and champion for ethical AI. Built SkillSail.ai after seeing how broken job search has become and won’t stop until the playing field is level.


Man wearing a suit and tie smiling.

Vahan Sagoian, Co-Founder & VP

Chris Osterhaug, Founder & CEO

Chris Osterhaug, Founder & CEO

 

Business development, partnerships, and startup ops.

Bio:
 

Engineer, operator, and attorney Vahan brings tech, legal, and business expertise from Microsoft and beyond. At SkillSail.ai, he’s making sure every big idea gets built, scaled, and protected.

Logo with pie chart and shield, titled 'Incoming CFO'.

CFO — To Be Announced

Chris Osterhaug, Founder & CEO

CFO — To Be Announced

 

Our next finance leader is a seasoned exec, former Fortune 500 manager, and trusted by our founder. With proven leadership and integrity, she’s the right partner to guide SkillSail.ai growth. Official announcement coming soon.

Collectively, our team brings experience from Microsoft, Fortune 500s, and successful startups. We’re here to build the future of hiring no shortcuts, no data games.

Copyright © 2025 SkillSail.ai - All Rights Reserved.

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

DeclineAccept