Olli Insurance

We make insurance easy.

Olli was built by entrepreneurs, insurance experts, and technologists with one mission: to make insurance feel easy and seamless for anyone.

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Our mission is to make insurance easy and seamless.

We believe protecting what you've built shouldn't be complicated. That's why we set out to build a platform that makes it effortless for anyone to embed, buy, sell, and manage insurance.

What We Do

For Solo Business Owners

We make insurance easy to understand, buy, and manage, helping independent workers get instant access to essential policies and the confidence of knowing they're properly protected. Olli removes the complexity so you can focus on building your business, not decoding insurance.

For Platforms

We offer API-first insurance infrastructure that enables gig platforms, marketplaces, SaaS companies, and membership organizations to offer integrated insurance directly to their users. Available as white-label, a widget, or a full API. Olli powers seamless embedded insurance across all 50 states.

Our Journey

2017

Olli's co-founders sell Rental Guardian, an embedded insurance company, to Greater Sum Ventures.

2018–2024

The team builds Arrk.io, an API-first insurance platform connecting syndicates, underwriters, MGAs, brokers, agents, TPAs, resellers, and end customers — serving clients primarily in the rental and housing industry.

2025

Olli is founded as a joint venture with Arrk.io to create the first insurance infrastructure built specifically for the business of one — combining modern technology with deep insurance expertise to serve solo entrepreneurs and the platforms that support them.

Our Values

The principles that guide everything we do

We build what works

We pioneer technology that simplifies insurance, delivering real-time solutions that help people get the protection they need without complexity or confusion.

We empower the bold

We back the people who take initiative, with transparent, tailored insurance that gives them the confidence to move faster.

We do business in the open

We operate with complete transparency and build trust with customers, partners, and team members through honest practices and real accountability.

We build bridges, not walls

We foster partnerships with carriers and tech leaders who share our vision, creating seamless experiences that actually solve problems.

We thrive on the impossible

We embrace change and challenges with optimism and grit, staying agile enough to navigate chaos and deliver what matters.

We champion the dreamers

We build for and with people who bet on themselves, and we make space for diverse perspectives in everything we do.

Meet the Olli Team

Focused on making insurance easy and seamless

Carrie Hartman

Carrie Hartman

CEO

Leads company vision, product strategy, and organizational growth.

Sean Miller

Sean Miller

COO

Builds and manages the operational systems that scale the business.

Christian Goy

Christian Goy

CMO

Oversees brand strategy, market positioning, and customer acquisition.

Donn Gore

Donn Gore

CIO

Directs platform engineering, technical architecture, and innovation.

CrisPaul Obana

CrisPaul Obana

CTO

Shapes Olli's data strategy, systems architecture, and digital infrastructure.

Beth Cavanaugh

Beth Cavanaugh

CCO

Guides compliance, carrier partnerships, and customer protection standards.

Join the movement

Whether you're building your own business or helping others grow theirs, Olli makes insurance easy to understand, buy, sell, embed and manage.

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