Sr. Manager, Technical Project Management

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 the Sr. Manager, Technical Project Management, you will lead and develop a growing team of TPMs while also staying deeply embedded in the work itself. This is a leadership role, but not a purely managerial one. We believe the strongest leaders in this function are people who can coach, guide, and raise the bar for the team because they themselves are highly capable practitioners of the work. In this role, you will set the vision, operating standards, and day-to-day effectiveness of the TPM function at Obie. You will lead the TPM team, own and evolve the TPM operating model, and directly support some of Obie’s most important XFN initiatives. You will help drive quarterly planning, resource alignment, execution visibility, spring and engineering Pod operations, and delivery maturity across Product and Engineering. You will serve as a stabilizing force across teams by bringing structure to ambiguity, clarity to planning, and accountability to execution. This role is ideal for a leader who is equally comfortable managing people, improving systems and process, and stepping in directly to run a complex initiative, facilitate alignment, or solve an execution problem when needed. The expectation is not just that you can lead TPM work, but that you understand it deeply enough to do it yourself when the moment calls for it. What you'll Do Lead, coach, and develop Obie’s team of Technical Project Managers, creating strong standards around execution, communication, accountability, and team growth. Lead Obie’s TPM function as a true player-coach - setting the vision and operating model for the team while staying close enough to the work to directly step into complex or high-priority initiatives when needed. Own and continuously improve how Product and Engineering plan and execute work, including quarterly planning, roadmap visibility, resource planning, implementation planning, Pod support, sprint/process rhythms, and XFN delivery coordination. Drive XFN planning and execution across major initiatives, partnering closely with Product, Engineering, Design, QA, PMO, and business stakeholders to maintain alignment, remove blockers, and ensure successful delivery. Partner closely with the VP of Product on executive and leadership-level strategic initiatives, helping translate high-level priorities into clear plans, strong execution, and operational follow-through across the organization. Manage scope, dependencies, and execution risk proactively, surfacing tradeoffs early and helping leadership make sound prioritization decisions without losing momentum. Build and mature the systems, tooling, and processes that support delivery excellence, including Jira workflows, automations, reporting structures, knowledge sharing, and broader TPM operational practices. Partner with Product, Engineering, and executive leadership to shape prioritization, planning, and execution decisions across the organization, ensuring the TPM function is helping drive the highest-impact work. Act as a trusted partner to senior leadership by creating confidence in execution, improving operational maturity, and bringing calm, thoughtful leadership to complex work across the organization. What you' ... (truncated, view full listing at source)