Obie logo and photographs of promoted team members on a decorative background

Obie Insurance Announces Key Leadership Promotions Ahead of 2024

Alex Roha
Nov 14, 2023

Obie names new CIO and CRO as it continues to set the new standard in investment property insurance

CHICAGO, IL. November 7, 2023 – Obie, a leading insurtech company for real estate investors, has announced today two significant updates to its executive team that will advance its mission to offer the new standard in investment property insurance.

Obie is pleased to celebrate the well-deserved appointments of two respected leaders. Laura Taccini Olson is now Obie’s Chief Insurance Officer (CIO) after previously serving as Chief Risk Officer. Brad Auerbach is now Obie’s Chief Revenue Officer (CRO) after previously serving as Obie’s first VP of Channels and Partnerships.

Laura Olson officially joined Obie in August 2021 and has brought both her remarkable leadership and expertise to Obie’s insurance offerings. Olson boasts over two decades of experience in the insurance industry, having worked with some of the world’s largest insurance companies.

Her diverse background spans product development, underwriting, analytics, compliance, operations, technology, and business development. Olson’s efforts have been recognized by numerous organizations as an innovative leader in the insurtech space, including HousingWire’s Insider award this year. 

As Chief Insurance Officer, Laura will oversee Obie’s insurance product and analytics, underwriting, service and program management teams.

Brad Auerbach has made an immediate impact on Obie's business and culture since joining the company last year. Prior to Obie, Auerbach served as a Director in Meta's Global Business Group where he was the founding member of its Insurance practice. At Meta, his team supported the digital transformation and marketing strategies of the country’s largest insurance carriers and insurtechs.

With over 15 years of experience building, scaling, and leading teams at both Meta and Microsoft, Auerbach’s appointment as CRO underlines Obie's commitment to leveraging the expertise of insurance and technology industry veterans. In his new role, Auerbach will oversee Obie’s Agency Development, Insurance Sales, Marketing and Partnerships teams.

“Both Laura and Brad’s profound expertise has significantly enhanced Obie's capabilities and offerings,” said Ryan Letzseiser, Co-Founder of Obie. “Their promotions reflect not only their immense value to the company but also their unwavering commitment to advancing Obie's insurance initiatives and supporting a culture of excellence.”

These promotions come in a year that has seen Obie reach new heights with the launch of the Obie Insurance Product in 49 states plus the District of Columbia and the announcement of its Series B funding round. 

“Obie’s customers are at the heart of its success, and our exceptional team is the driving force behind our momentum as we look forward to 2024,” said Aaron Letzeiser, Co-Founder of Obie.”

About Obie

Obie is an insurance technology company, hyper-focused on driving value for the modern real estate investor and the partners they work with every day. Whether you are an owner, lender, agent, or property manager, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold. Learn more at

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