Acquisition
Jan 2026The 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
Company research
Public company, workplace, funding, and market signals
Updated Jul 29, 2026
Overview
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
Chicago, IL (HQ)
San Francisco, CA
Tampa, FL
Business model
embedded insurance platform
direct-to-investor digital brokerage
partner/API distribution
independent agent distribution
Funding
People & investors
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
Work & culture
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
medical insurance
dental insurance
vision insurance
life insurance
telehealth
401(k) matching
paid parental leave
flexible PTO
wellness stipend
education stipend
pet insurance reimbursement
company equity
FSA/HSA
equipment budget
professional development support
Product & market
Pricing
Quote-based insurance premiums; no public list pricing.
Differentiators
- —instant bindable quotes in minutes
- —data-enriched underwriting using 1,000+ data points
- —built for landlords and real estate investors
- —embedded API/partner distribution
- —works with direct-to-investor and agent channels
- —broad product set for rental, short-term rental, master policy, and renovation coverage
- —nationwide coverage across all 50 states
Technology
AWS
React
PostgreSQL
Node.js
TypeScript
JavaScript
GraphQL
Salesforce
GitHub
GitHub Actions
Playwright
Cypress
Jest
Figma
Slack
HubSpot
Confluence
Jira
Google Workspace
FullStory
Customers
landlords
real estate investors
property managers
lenders
agents
technology partners
investment-property owners
small-to-medium apartment landlords
single-family rental owners
portfolio investors
Competitors
Honeycomb
Steadily
Kin
Openly
Swyfft
Neptune Flood
Delos
Velocity Risk Underwriters
Scale & contact
Estimated revenue
USD 10M-20M
Estimated monthly visits
64.3K
Traffic estimate as of Jul 2026
Signals & risks
Latest news
Obie 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.
Jobs and careers at Obie
5 jobs at Obie
Product Manager
Remote
Product & Engineering
Remote (United States)
3d ago
Remote
Full-time
Insurance Program Analyst
Remote
Insurance
Remote (United States)
1w ago
Remote
Full-time
Underwriter
Remote
Insurance
Remote (United States)
3w ago
Remote
Full-time
Data Analyst
Remote
Insurance
Remote (United States)
1mo ago
Remote
Full-time
Come work for Obie!
Remote
General
Remote (United States)
2y ago
Remote
Full-time