Senior Data Engineer, Obie

$105-175k

+ Equity participation opportunities

SQL

AWS

TypeScript

JavaScript

Python

Postgres

dbt

Senior and Expert level

Chicago

Remote from US

More information about location

Insurance for landlords and real estate investors

Be an early applicant

Insurance for landlords and real estate investors

101-200 employees

B2BMarketplaceProductivityInsuranceReal Estate

Be an early applicant

$105-175k

+ Equity participation opportunities

SQL

AWS

TypeScript

JavaScript

Python

Postgres

dbt

Senior and Expert level

Chicago

Remote from US

More information about location

101-200 employees

B2BMarketplaceProductivityInsuranceReal Estate

Company mission

To provide a simple, affordable, and transparent insurance experience for landlords and real estate investors.

Job

Company

Role

Who you are

This is a high-impact role for someone who thrives on technical depth, cross-functional collaboration, and the chance to leave things better than they found them
7+ years of experience in data engineering or analytics, ideally in Property & Casualty insurance
Strong experience with SQL, scripting in Python (and optionally JavaScript/TypeScript), and querying SQL-based systems
Deep familiarity with AWS cloud services, especially S3 and managed databases
Experience with cloud data warehouses, orchestration tools, and modern data modeling practices
Excellent technical writing and documentation skills
Ability to work independently and deliver on complex projects with minimal guidance
Strong communication skills and comfort working in a matrixed, cross-functional environment

What the job involves

We’re looking for a Senior Data Engineer to join our growing data analytics team and help build the systems that power data-driven decisions across Obie
You’ll own end-to-end pipelines, shape how data flows through the organization, and collaborate with stakeholders across teams—especially within our Insurance division
Design, build, and maintain end-to-end data pipelines from source systems to user-facing analytics
Develop modeled warehouse tables using the Data Vault 2.0 framework
Translate business needs into technical solutions by collaborating with analysts, product managers, and leadership
Build and maintain ad-hoc and temporary data solutions to keep teams unblocked
Champion data quality and governance, including defining key metrics, building glossaries, and documenting data lineage
Work within Obie’s current stack—and help us evolve it—with tools like AWS, PostgreSQL, Python, SQL, dbt, and orchestration platforms

Application process

We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:
Intro Chat (30 min.)
A conversation with Kara or Skylar to get to know you—and let you get to know Obie
Hiring Manager Interview (45 min.)
A deeper technical discussion with Curtis Jackson, focused on your experience and how you approach data challenges
Take-Home Exercise
You’ll complete a short project using Python and SQL, working with realistic data from our world of real estate insurance. Our tech stack includes AWS S3 and PostgreSQL, so familiarity there will help
Team Interview (1 hour)
You’ll meet a few members of the team to talk through your approach and explore how we’d work together

Our take

Obie is transforming how landlords across the US access insurance for their properties. Through its tefch0druiven platform, landlords can easily get instant quotes, connect with the right insurance provider, and secure coverage - all without the hassle of paperwork or complicated processes. The company insurers over $25M in properties across all 50 states, offering a simple and affordable alternative to traditional insurance.

Focusing on small-to-medium-size rental properties, Obie addresses the challenges landlords face with poor pricing and inadequate coverage. By leveraging technology, the company provides customized, industry-best rates and a straightforward online experience.

Now the company plans to evolve further by utilizing its data and client base to potentially become its own insurance carrier. With strong funding to its name, the company is well-positioned for continued growth and to reshape the future of landlord insurance.

Steph

Company Specialist at Welcome to the Jungle

Insights

Top investors

26% employee growth in 12 months

Glassdoor (4.9)

Trustpilot (4.3)

Company

Funding (last 2 of 5 rounds)

May 2023

$25.5m

SERIES B

May 2021

$10.7m

SERIES A

Total funding: $39.2m

Company benefits

Medical, Dental, Life, Vision
401(k) Matching
Pet Insurance
Paid Parental Leave
Hotel Discounts
Telehealth
Flexible Time Off
L&D Stipend
Wellness Stipend
Benefit Support Tools

Company HQ

West Loop, Chicago, IL

Leadership

Ryan Letzeiser

(Co-Founder & CEO)

They studied at Clemson University before working as a Real Estate Investment Analyst, and becoming an Investment Associate at Hudson Capital Investments. They joined MAC Properties in March 2015 as a Managing Member in 2015, before co-founding Obie in July 2018.

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