Overview
Josh Ettwein serves as Chief Technology Officer at Ascertain[1][3]. Ettwein is a technology executive and product leader with over 20 years of experience building and scaling engineering and product organizations across early-stage startups and companies through acquisition[2]. Ettwein's background includes deep expertise in healthcare technology, including leading teams through HITRUST certification, EHR implementations, and value-based care contracts[2]. Prior to joining Ascertain, Ettwein held the position of Vice President of Engineering at Rippl from February 2023 to April 2026, contributing to the company's acquisition by Harbor Health[2][4]. Earlier roles include Head of Product Engineering at Curai Health[5], Head of Engineering and Product Development at Blue Rocket Incorporated[6], and Director of Software Engineering at MatrixCare[7]. Ettwein also co-founded TrepScore, serving as Co-Founder and CTO[8]. Ettwein holds an Associate of Arts degree in Environmental Science and a degree in Earth Science from the University of New Hampshire[11][12].
Profile introduction
Technology executive and product leader with 20+ years building and scaling engineering and product organizations, from early-stage startups through successful acquisitions. Deep expertise in healthcare technology, having led teams through HITRUST certification, EHR implementations, and value-based care contracts. Proven track record of driving M&A outcomes - most recently as a key contributor to Rippl's acquisition by Harbor Health. Combines technical depth with product instincts to deliver software that moves business metrics.
Career history
- Chief Technology OfficerApr 2026 to presentAscertain
- Vice President of EngineeringFeb 2023 to Apr 2026Rippl
- Head of Product EngineeringJan 2022 to Feb 2023Curai Health
- Head of Engineering and Product DevelopmentJan 2020 to Jan 2022Blue Rocket Incorporated
- Director of Software EngineeringApr 2015 to Dec 2019MatrixCare
- Co-Founder & CTOSep 2013 to Apr 2015TrepScore
- Director of Engineering, User ExperienceApr 2012 to Sep 2013PRIMA Cinema, Inc.
- Director of Engineering and Product DevelopmentOct 2008 to Apr 2012Sorenson Media
Education
Earth ScienceUniversity of New Hampshire
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