Senior Manager of Program Management

Location: Westlake

Time Type: Full time

Job Description

Position Summary

The Senior Manager, Program Management is responsible for leading the planning and execution of complex, cross-functional product and technology programs across an independent insurance brokerage. This role works closely with Product Management, Technology leadership, software development teams, and senior business stakeholders to ensure strategic initiatives move effectively from roadmap to execution.

The Senior Manager may oversee initiatives spanning multiple products, development teams, business functions, external partners, and technology platforms and may provide leadership, coaching, and direction to Program Managers, Project Managers, or other delivery professionals. This role will manage a team of Program Managers and will be critical in the development of the practice within our technology organization.

Key Responsibilities

• Lead execution of large, complex programs spanning multiple products, development teams, business functions, and strategic initiatives.

• Partner with Product Management leadership to translate 12-month roadmaps and multi-year strategies into coordinated execution plans.

• Establish integrated program plans connecting product priorities, technology delivery, business readiness, dependencies, and major milestones.

• Work closely with Product Managers, Principal Product Managers, engineering leaders, architects, UX/design, data, QA, and other technology teams.

• Partner with senior business stakeholders to establish program objectives, success measures, priorities, decision-making processes, and accountability.

• Establish governance and operating rhythms appropriate to program size and complexity.

• Identify and manage dependencies across products, platforms, development teams, business functions, carriers, external partners, and third-party vendors.

• Proactively identify program risks, issues, resource constraints, and execution challenges and drive teams toward resolution.

• Facilitate complex cross-functional decisions and ensure appropriate escalation.

• Provide executive-level communication regarding program health, progress, milestones, risks, dependencies, decisions, and expected outcomes.

• Coordinate product and technology delivery with operational processes, training, communications, compliance, implementation, and adoption.

• Ensure programs have clearly defined ownership, milestones, deliverables, success measures, and accountability.

• Create transparency into sequencing, capacity constraints, dependencies, and potential impacts to strategic objectives.

• Partner with Product and Technology leadership on quarterly and annual planning, roadmap execution, capacity discussions, and major initiative sequencing.

• Establish consistent program-management standards, tools, artifacts, reporting, and best practices.

• Drive continuous improvement in how the organization plans, manages, communicates, and executes strategic initiatives.

• Coach and mentor Program Managers, Project Managers, and other team members; may directly manage delivery professionals.

Qualifications

• Bachelor's degree in business, technology, project management, or a related field preferred.

• 8+ years of progressive project management, program management, technology delivery, implementation, or related experience.

• Demonstrated experience leading complex programs involving multiple products, technology teams, and business functions.

• Significant experience partnering with Product Management and software development organizations.

• Experience working within Agile product and software development environments.

• Exceptional written and verbal communication skills, including executive-level communication.

• Strong facilitation, stakeholder-management, organizational, and problem-solving capabilities.

• Demonstrated ability to influence cross-functional teams and drive outcomes without direct authority.

• Experience establishing program governance, operating rhythms, portfolio reporting, and executive communications.

• Experience coaching or leading Program Managers, Project Managers, or cross-functional delivery teams preferred.

• Certifications or formal training such as PMP, Agile, Lean, SAFe, Scrum, or similar methodologies desired but not required.

• Experience within SaaS, insurtech, fintech, insurance technology, or another technology-driven environment preferred.