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 Director, 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'll Bring

• Significant experience in Technical Project Management, Program Management, Engineering Program Management, or a similar delivery leadership role within a software or product organization.
  
• Prior people leadership experience, including direct management, coaching, performance feedback, and team development, with a clear ability to raise standards and grow strong operators.
  
• A strong belief in hands-on leadership - you are comfortable leading the TPM function while also staying close enough to the work to step in directly when needed.
  
• Proven success driving complex, XFN initiatives from planning through execution and release in environments with multiple teams, shifting priorities, and high ambiguity.
  
• Strong command of delivery operations, including quarterly planning, roadmap execution, resource planning, dependency management, risk management, milestone planning, and launch readiness.
  
• Strong technical fluency and the ability to work effectively with engineers on implementation tradeoffs, technical dependencies, systems constraints, APIs, testing, and release sequencing.
  
• Experience partnering effectively with senior product, engineering, and executive leaders on strategic initiatives, organizational planning, and cross-functional execution.
  
• Excellent communication, judgment, and executive presence, with the ability to influence across senior leadership, build trust across functions, and create clarity in complex situations.
  
• Experience improving operating systems and team processes over time, including strong working knowledge of Jira / Atlassian tools as meaningful levers for planning, visibility, and execution.
  
• The ability to balance strategic leadership with tactical depth - zooming out to shape the function and zooming in when details matter.

When applying, be sure to include your favorite emoji so we know that you’re a real human, who also loves emojis!

Interview Process

At Obie, transparency is core to our interview 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:

• Our company’s blog to learn more about the market we serve and the information our customers value.
• Check out our LinkedIn to see how people interact with our brand and product.
• Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insurtech Amplified Podcast

1. Meet us and get to know Obie
   You'll first talk to Kara on a 30-minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product.
2. Meet the hiring manager
   Next,  you'll get to have a 45 minute video interview with the hiring manager, Adam Tsouras, to assess your technical skills.
3. Complete a Project Exercise
   This role requires exceptional leadership, planning, collaboration, and communication skills, so we’ll also present you with a short exercise designed to reflect the real work of a Director-level TPM leader at Obie. The exercise will give you an opportunity to demonstrate how you approach team leadership, XFN delivery, prioritization, operational process, and stakeholder communication in a fast moving environment. Because this is a senior leadership role, we’ll be looking not only at how you would execute the work yourself, but also how you would guide a team, create clarity, drive alignment, and build confidence across the organization. You’ll complete the exercise on your own time, so please be thoughtful and thorough in your response. We’ll be evaluating your problem-solving abilities, written communication, judgment, empathy, leadership presence, and your ability to bring structure to ambiguity while balancing strategic thinking with practical execution. More on this when you get there.
4. Meet the Team
   Since you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better

Moving Forward with Obie

Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.

Obie has you Covered

Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.