Data Analyst

Responsibilities

Develop hypotheses to understand the state of the business, such as drivers of growth or stagnation

Conduct analyses providing insight into critical business questions

Build and maintain dashboards / reports within our Business Intelligence / Data Visualization tool Sigma

Align and support various analytics, metrics, data, and reporting needs at Obie across various departments like Growth & Channel Distribution, Product & Engineering, Insurance, Finance & Accounting, and the Executive team in collaboration with Data Engineers, Insurance Product Analysts, and Operations Analysts

Support financial budgeting, forecasting, and tracking

Perform data quality checks and reconciliations to datasets as needed

Serve as a trusted advisor to all stakeholders of data, answering reporting, metric, and data questions, and facilitating a culture of data literacy and data-driven decision making

Preferred

Experience in insurance, financial services, or similar

Experience with another analytics tool like python, R, or similar

Experience working with AI (We use Claude), github, and dbt

Experience in strategy, operations and analytics, GTM analytics, financial forecasting, consulting, or similar

Benefits

Remote (United States)

Chicago-based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.

Comprehensive health, dental, vision and life insurance

Flexible paid time off

Retirement savings plan with company match

Obie is an insurance company that specializes in rental property and landlord insurance services. It is a sub-organization of The Baldwin Group.

Chicago, Illinois, USA

https://www.ObieInsurance.com

Growth Stage

Total Funding

$39M

Key Investors

Battery Ventures

Y Combinator

2026-01-13

Acquired

2023-05-17

Series B· $25.5M

2021-05-26

Series A· $10.7M

Leadership Team

Ryan Letzeiser

Co-Founder & CEO (YC S19) - Acquired Jan 2026 (BWIN - Nasdaq)

Aaron Letzeiser

Co-Founder & President

Recent News

Coverager - Insurance news and insights

Dell’s Darlings

2026-09-19

nar-reach.com

Qualifications

Those successful in this role will have a good mix of technical skills (SQL, python, data visualization, AI), business acumen, and insurance or financial services knowledge

Strong ownership abilities and interpersonal skills are critical for the individual in this role

Experience in data analytics or business analytics with strong SQL abilities

Knowledge and interest in insurance

Ability to drive initiatives start to end and manage competing priorities

Ability to dive deep into the data and details while synthesizing the bigger picture for stakeholders

Strong interpersonal, communication, and leadership skills

Team player attitude with the desire to drive impact at a fast growing company

Experience in insurance, financial services, or similar

Experience with another analytics tool like python, R, or similar

Experience working with AI (We use Claude), github, and dbt

Experience in strategy, operations and analytics, GTM analytics, financial forecasting, consulting, or similar

Required skills

SQL, Data Analytics, Insurance, Financial Services, Python, R, Claude, GitHub, dbt, Financial Forecasting, Go-to-Market Analytics

Preferred skills

Experience in insurance, financial services, or similar, Experience working with AI (We use Claude), github, and dbt

Experience

Mid level