Great Road Holdings is a private investment firm based in Harrison, New York, that makes growth equity investments in promising companies looking to expand proven revenue streams, as well as value-oriented special situation equity and debt investments in diversified and defensible businesses.
46% of their portfolio is in Education. Average disclosed round size is $15.8M (across 22 rounds with reported amounts).
Portfolio
15
Fund Size
—
Top Stage
Series B
Last 12 Mo
0
Team
JS
James Shifren
Partner, Founder
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
DealsAvg Round Size
Portfolio
24 investments
| Company | Round | Amount | Date |
|---|---|---|---|
 Cyware | Series C | $30M | Jun 2023 |
| CCybrary, Inc. | Series C | $25M | Jan 2022 |
| Cyware | Series B | $30M | Mar 2021 |
| Cyware | Series A | $10M | Aug 2020 |
 PresenceLearning | Series D | $27M | May 2020 |
| CCyware | Series A | $30M | Jan 2020 |
 Redshelf | Series C | $25M | Jan 2018 |
 Tuition.io | Series B | $7M | Jan 2017 |
 PowerSchool | Series D | $32M | Nov 2015 |
 Schoology | Series D | $32M | Nov 2015 |
 Babbel | Series C | $22M | Jul 2015 |
| Tuition.io | Series A | $5M | Jan 2015 |
 Speexx | Series B | — | Jan 2015 |
 MasteryConnect | Series A | $15.2M | Sep 2014 |
| Schoology | Series C | $15M | Jan 2014 |
| PresenceLearning | Series B | $8M | Apr 2013 |
| Babbel | Series B | $10M | Mar 2013 |
 LearnZillion | Series A | $7M | Jan 2013 |
| LearnZillion | Seed | $2.4M | Jan 2012 |
| PPurple Squirrel | Seed | $2.7M | — |
| MasteryConnect | Seed | $1.1M | — |
| MasteryConnect | Series C | $4.5M | — |
| XXueXiBao | Series B | — | — |
 Brainstorm | Series A | $6.4M | — |
Top Co-Investors
Prelude Ventures4 shared
Emerald Development Managers4 shared
Learn Capital4 shared
Zscaler3 shared
Advent International3 shared
JMI Equity3 shared
Intel Capital3 shared
FirstMark Capital3 shared
NewSchools Venture Fund3 shared
New Markets Venture Partners2 shared
Elevate Ventures2 shared
Reed Elsevier Ventures2 shared
MassMutual2 shared
Mohr Davidow Ventures2 shared
Wildcat Capital Management2 shared
Trinity Ventures2 shared
TenEleven Ventures1 shared
Great Oaks Venture Capital1 shared
Crosscut Ventures1 shared
Arena Holdings1 shared
Last updated: 19 September 2026