How many investments has Greenlight Re made?

Greenlight Re has 10 tracked investments.

What stage does Greenlight Re invest at?

Greenlight Re invests at the Seed, Series A stages.

What sectors does Greenlight Re focus on?

Greenlight Re focuses on InsurTech.

Where is Greenlight Re located?

Greenlight Re is headquartered in Grand Cayman, KY.

Greenlight Re

Corporate VC

Grand Cayman · Seed–Series A · 7 people tracked

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Investment thesis

Greenlight Re Innovations evaluates and partners with early-stage technology startups developing solutions applicable to the insurance and reinsurance sectors, supporting innovation in risk management and insurance technology.

Invests inInsurTech Global Grand Cayman Ireland United Kingdom

Source: firm website, verified Sep 20, 2026.

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Stage

Seed–Series A

Grand Cayman, KY

Instruments

Equity

Founded

2004

Tracked investments

Team · 7 people

from the firm's website & curated & public directories

Samuel Clifton· Principal· London

Focuses on investing in and supporting insurtech startups and emerging MGAs across the UK and Europe. Started his career at Jaguar Land Rover's venture capital arm InMotion Ventures investing in early-stage transportation startups, then founded and scaled venture-backed companies with a focus on sales and go-to-market strategy.

Alex Whitney· Principal· Cayman Islandsin

Joined Innovations in 2021 to source and evaluate investment opportunities and support portfolio company growth. Previously worked as an investor at ManchesterStory, a venture capital firm focused on insurtech, fintech, and digital health, and supported investment processes at DLA Venture Fund.

Kagabo Ngiruwonsanga· Chief Underwriting Officer - Innovations

Oversees underwriting for the Innovations unit with over 20 years of property and casualty insurance experience. Joined Greenlight Re in 2011 as an actuary and previously worked at Liberty Mutual and MetLife in pricing and catastrophe modeling roles.

Tom Hemmings· Innovation Underwriter· Grand Caymanin

Joined the Innovations team in 2024 with prior (re)insurance underwriting experience at Aspen and Arch Re in casualty treaty underwriting.

Wang Xu· Innovations Underwriter and Analytics Lead· Cayman Islandsin

Joined Innovations in July 2025 with extensive experience in the ILS and (re)insurance markets across various regions. Previously worked at Ledger Investing, Peak Re, Greenlight Re, Verisk, and AIG.

Enrico Costanzo· Head Of Innovation· Paris, Île-de-France, Francein

Holds a Ph.D. in Molecular Biology and MBA with experience at Air Liquide's innovation lab. Leads the Research & Innovation Department at Cereal Docks, focused on advancing from commodities to food ingredients and establishing collaborations with universities and startups in foodtech and agriculture.

Brian OReilly· Head of Innovations· George Town, Cayman Islandsin

Brian O'Reilly serves as Head of Innovation at Greenlight Re, where he leads the company's innovation division. In this role, he evaluates insurance technology applications and oversees partnerships with early-stage startups, providing investment capital, risk capacity, and strategic guidance to support their growth.

What they invest in

from 9 of 10 portfolio companies

AI & Machine Learning ×7InsurTech ×7Fintech ×5Enterprise Software ×2Construction Tech ×1Data & Infrastructure ×1EdTech ×1Hardware ×1

HQs:United States×6Canada×1

Investments · 10 tracked

founders shown can be your intro path

By year:2024 · 4 2023 · 2 2022 · 1 2019 · 18 dated

Viverepartnersviverepartners.com✓ verified

Vivere is a specialty insurance platform for managing general agents (MGAs) and their capacity partners, using technology and alternative data to give underwriters operational infrastructure and portfolio transparency.

AI & Machine LearningFintechInsurTechLaguna Beach, US

Sachith Gullapalli(Founder)

Co-investorsPathlight Ventures General Catalyst

Armilla AIarmilla.ai inFeb 2024 · $4.5M

Armilla AI is a managing general agent offering liability coverage, performance warranties, and risk assessments for AI systems.

AI & Machine LearningData & InfrastructureEnterprise SoftwareFintechInsurTechToronto, CA

Dan Adamson(Founder)in Karthik Ramakrishnan(Founder and CEO)inBaiju Hasmukhrai Devani(Executive Officer, Director)

Board Raif Barbaros(Director)in

Co-investorsBeresford Ventures Betaworks Creative Destruction Lab (CDL)Differential Ventures Mistral Venture Partners MS&AD Ventures +8 more

Openlyopenly.com in 𝕏Nov 2019 · $7.7M

Openly provides home insurance products and services for independent agents and consumers through a technology-enabled platform.

FintechInsurTechBoston, US

Ty Harris(CEO and Co-Founder)in Matt Wielbut(Co-Founder)in Matt Wielbut 🦄(Founder)inTyree Harris(Executive Officer, Director)Mateusz Wielbut(Executive Officer, Director)

Co-investorsAdvance Venture Partners Clocktower Ventures Drive Capital Gradient Ventures MTECH CAPITAL Obvious Ventures +3 more

Redkikredkik.com in 𝕏

Redkik provides embedded, transactional insurance software that integrates via API at the point of sale, using AI and machine learning to analyze data points and generate dynamic quotes and risk-management tools for cargo, warehouse, gap, and spike coverage.

AI & Machine LearningInsurTechLogistics & Supply ChainEaston, US

Chris Kalinski(Founder & CEO)in

Co-investorsFinTech Ventures MS&AD Ventures Redstone

Scriptionscription.comOct 2023 · $2.5M

Scription is a commercial HVAC insurance program that covers a building operator's rooftop unit fleet for a single flat annual premium, taking on repair and breakdown cost volatility while the operator keeps its existing providers, CMMS, and workflows.

AI & Machine LearningInsurTechPropTech

Justin Villiers, M.Sc.(Founder)in

Co-investorsConnetic Ventures Hustle Fund Markd Startup TNT

Scriptionscription.aiOct 2023 · $2.5M

Scription offers a commercial HVAC insurance program that covers rooftop unit fleets for a single fixed annual premium, with a licensed carrier and reinsurance holding the risk and paying repair claims.

AI & Machine LearningFintechInsurTech

Co-investorsAlumni Ventures Cameron Ventures Startup TNT Connetic Ventures Hustle Fund Markd

Shepherdshepherdinsurance.com in 𝕏Feb 2024 · $13.5M

Shepherd combines underwriting expertise with technology to modernize commercial insurance risk selection, pricing, and servicing.

Construction TechFintechInsurTechSan Francisco, US

Mo Mahallawy(Cofounder / CTO)inJustin Levine(Founder)in

Co-investorsEra Ventures On Deck Y Combinator AirAngels Costanoa Ventures Intact Ventures +3 more

Shepherdshepherd.study 𝕏Feb 2024 · $13.5M

Shepherd provides schools with a learning platform that integrates AI-powered study tools, tutoring access, peer collaboration features, and progress tracking to offer students personalized academic support.

AI & Machine LearningEdTechMarketplaces

Moyosoreoluwa Orekoya(Founder)in Marcella Imoisili(Founder)in Kehinde Williams(Founder)in

Co-investorsY Combinator Costanoa Ventures Era Ventures Intact Ventures Spark Capital

Shepherdaskshepherd.ai inFeb 2024 · $13.5M

Shepherd is an AI assistant that integrates with a team's existing tools (messaging, code editors, CRM platforms) to create a unified memory system.

AI & Machine LearningEnterprise SoftwareHardwareSaaSSan Francisco, US

Philip Meng(Founder, CEO)in Ishan Ramrakhiani(Founder)in Elijah Renner(Founder)in

Co-investorsY Combinator Costanoa Ventures Era Ventures Intact Ventures Spark Capital

Other

Tracked investments with no reachable website or further public details — typically companies that wound down, renamed, or were absorbed.

InRev

Portfolio news

latest coverage across their companies

Openly secures growth funding and expands Allianz Re partnership

Openly · fintech.global · Apr 24, 2026

Shepherd Raises $42M Series B Funding

Shepherd · finsmes.com · Mar 24, 2026

Armilla AI raises $25m to expand AI liability coverage

Armilla AI · fintech.global · Jan 23, 2026

Scription Raises $7.8M in Seed Funding

Scription · finsmes.com · May 13, 2025

Frequently asked questions

How many investments has Greenlight Re made?: Greenlight Re has 10 tracked investments.
What stage does Greenlight Re invest at?: Greenlight Re invests at the Seed, Series A stages.
What sectors does Greenlight Re focus on?: Greenlight Re focuses on InsurTech.
Where is Greenlight Re located?: Greenlight Re is headquartered in Grand Cayman, KY.

Co-investors · 1

Mouro Capital

Mouro Capital is a venture capital investor backing early to growth stage companies, leveraging its expertise and global network across multiple regions.

$1M – $15M

Firms observed investing alongside Greenlight Re, from public investor directories. Shared companies are the overlap with Greenlight Re's recorded portfolio.

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