Technical Project Manager

At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be.

Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.

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

Brief Summary of Role

As a Technical Project Manager (TPM), you’ll drive end-to-end delivery for some of Obie’s most important product and platform initiatives - with a particular emphasis on supporting our insurance product work as it expands (new lines of business, partner/business requests, and delivery across multiple engineering pods).

You’ll bring structure to ambiguity, translate goals into clear execution plans, and keep teams aligned as we ship in a fast-moving environment. You’ll coordinate scope, dependencies, risks, and release readiness while maintaining a high bar for quality - and you’ll be especially strong at protecting teams from scope creep by helping stakeholders make clear tradeoffs.

What you'll do

• You speak fluent project management:  You’ll manage objectives, scope, timelines with stakeholders across both business pillars and engineering pods. You’ll spot risks early and keep everyone in the loop on progress made and aligned on the path forward.
• Scope and tradeoffs are your superpower: Proactively manage scope creep, clarify decisions, and help stakeholders make tradeoffs so teams can execute predictably.
• You can herd cats while juggling flaming torches: You’ll track and report progress from kickoff to delivery, aligning project milestones with company goals all while coordinating with engineers, technical specialists, and PMs.
• You bring order to the sprint shaped chaos: You’ll facilitate sprint planning and ceremonies for an engineering pod, ensuring accountability, clarity, and momentum toward quarterly goals.
• Quality is your bar: Partner with QA/Engineering/Product to define acceptance criteria, coordinate test planning, facilitate QA/business readiness reviews, and ensure release confidence (without being the primary “test case writer” or PR reviewer).
• You see both the forest and the tech stack: You’ll work closely with engineering to understand high level constraints and opportunities, making sure solutions are scalable, practical, and aligned with our architecture goals.
• You’re the glue that holds the pod together: You’ll build strong lines of communication with stakeholders and maintain transparency on goals while operating independently to get the job done.
• You can work async: You will be able to work independently and make decisions with minimal supervision. You also will be able to demonstrate your excellent communication skills, including the ability to build relationships internally and externally.

What you'll bring

• Proven track record owning the product lifecycle as a Technical Project Manager or similar role, with deep familiarity in project management principles and Agile frameworks.
• Excellent analytical, organizational and project management skills with strong written, verbal, and interpersonal communication.
• Flexible, adaptable, and solutions-oriented when facing challenges; skilled at balancing competing priorities in fast-paced environments and pushing back on leaders and stakeholders when necessary.
• Ability to multitask and to manage multiple priorities across multiple teams that are geographically distributed, while maintaining transparency and collaboration.
• Demonstrated experience driving delivery with engineering teams (requirements -> execution -> release), including navigating ambiguity and competing priorities.
• Attention to detail for thorough quality assurance and product testing.
• Proven examples of managing scope creep and driving decisions/tradeoffs.
• Passionate about continuous improvement, learning, and sharing best practices; proactive with strong follow through.
• Proficiency with Atlassian suite.

Icing on the cake (nice to haves)

• Exposure to insurance / fintech / regulated domains (or adjacent complexity where business constraints matter)..
• Prior experience in product management or product-heavy TPM work (strong product intuition and domain ramp).
• Technical fluency (comfortable reading specs, API concepts, and system constraints)

Click here for some insight into our culture!

The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.