Senior Manager of Technical Project Management, Obie
$125-175k
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
Be an early applicant
$125-175k
More information about location
101-200 employees
Company mission
To provide a simple, affordable, and transparent insurance experience for landlords and real estate investors.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
- 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
Application process
- When applying, be sure to include your favorite emoji so we know that you’re a real human, who also loves emojis!
- 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
- 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
- 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
- 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 Sr. Manager-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
- 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
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
26% employee growth in 12 months
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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