Sr. Manager, Technical Project Management

Obie is a company that provides innovative insurance solutions for real estate investors and landlords. They are seeking a Sr. Manager of Technical Project Management to lead and develop a team of Technical Project Managers, drive cross-functional initiatives, and improve operational processes within the organization.

Responsibilities:

• 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

Requirements:

• 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