The Baldwin Group completed its acquisition of Obie (Creisoft, Inc. and subsidiaries), making Obie part of Baldwin's underwriting/capacity/technology solutions platform.
SourceMoving Investment Property Insurance Forward
Public company, workplace, funding, and market signals
Updated Jul 29, 2026
Chicago-based insurtech for landlords and real estate investors; Obie offers fast, bindable rental-property insurance through digital, embedded-partner, and agent channels, and was acquired by The Baldwin Group in January 2026.
Primary product
Embedded insurance and landlord/investment-property insurance for real estate investors
Founded
2017
Headquarters
Chicago, Illinois, United States
Team size
90-100
Work style
Hybrid
Industry
Insurance
Sub-industry
Insurtech / embedded insurance for investment properties
Offices
2 jobs at Obie
Business model
Leadership
Co-Founder & CEO
Co-Founder & COO
Chief Technology Officer
Chief Insurance Officer
Chief Revenue Officer
Head of Software Engineering
Head of Distribution and Partnerships
Director of Engineering
VP Underwriting Operations & Compliance
Investors
Mission-driven, transparent, and data-driven; emphasizes flexibility, collaboration, customer focus, and recognizing employee impact.
Work style
Hybrid
Compensation
Obie publicly posts salary ranges on some roles and says it benchmarks compensation with real-time market data from venture-backed companies, typically targeting the midpoint of the range. Example public ranges include $19-$27/hour and $50k-$70k/year.
Benefits
Pricing
Quote-based insurance premiums; no public list pricing.
Differentiators
Technology
Customers
Competitors
Estimated revenue
USD 10M-20M
Estimated monthly visits
64.3K
Traffic estimate as of Jul 2026
The Baldwin Group completed its acquisition of Obie (Creisoft, Inc. and subsidiaries), making Obie part of Baldwin's underwriting/capacity/technology solutions platform.
SourceObie LinkedIn · Jul 2026
Obie announced Builder's Risk coverage for eligible renovation projects, expanding its coverage for value-add and rehab workflows.
Obie · Apr 2026
Obie said Aaron and Ryan Letzeiser were named finalists for EY's 2026 Midwest Entrepreneur Of The Year award and highlighted continued growth in coverage and premium.
The Baldwin Group / Business Wire · Jan 2026
The Baldwin Group completed its acquisition of Obie, expanding Baldwin's embedded insurance distribution capabilities and folding Obie into its underwriting/capacity/technology solutions unit.
Business Wire · Apr 2025
Obie launched a new brand identity and said it had secured $60B in coverage and written over $200M in premium.
Business Wire · Jan 2025
Obie launched PolicyProof, a compliance automation and liability product for property managers, pairing policy tracking with Master General Liability coverage.