Program Manager - Insurance Experience

The Baldwin Group • Tampa, FL

3d

About The Position

The Baldwin Group is seeking a Program Manager to lead a multi-million-dollar, multi-workstream program within their insurance operations, technology, and partner ecosystem. This role requires end-to-end execution of complex, cross-functional initiatives, serving as the connective tissue between executive leadership and execution teams. The Program Manager will engage with Product Owners to assess and prioritize customer feedback while driving execution via mature Agile practices, with experience in standard SDLC in an Agile environment being essential. The ideal candidate will have a sharp business mind, a proven ability to strategize and implement high-level program initiatives, and experience in managing and coaching staff of different disciplines to produce results. The goal is to ensure all programs deliver desirable outcomes to the organization, requiring the ability to make frequent trade-offs between business targets and project/operational performance.

Requirements

• 8+ years of progressive experience in program management, portfolio management, or senior project management roles within financial services, insurance, or a similarly regulated industry.
• Proven ability to manage complex, multi-workstream programs with budgets, cross-functional teams, and third-party vendors simultaneously.
• Experience working with offshore teams.
• Strong background in risk management, change management, and strategic planning.
• Experience managing technology programs, including infrastructure, application development, system integrations, production certification processes and production support in a 24 x 7 environment.
• Exceptional stakeholder management skills with a track record of effectively engaging executives, directors, and frontline teams.
• Proficiency in Agile and traditional (Waterfall) project management methodologies.
• Outstanding written and verbal communication skills; ability to translate technical details into executive-ready narratives.
• Bachelor's degree in business administration or information technology preferred.
• Certified Scrum Master (CSM) or Certified Scrum Product Owner (CSPO).
• Experience managing large-scale compliance or regulatory programs (e.g., PCI, IAM, data governance).
• Scrum agile methodologies implementation experience.
• Experience with software development best practices including Scaled Agile, TDD and Continuous Integration; a track record of applying these methodologies.
• Thorough understanding of project/program management techniques and methods.
• Excellent listening, interpersonal, written, and oral communication skills.
• Exceptional leadership, time management, facilitation, and organizational skills.
• Excellent coaching and problem-solving ability.
• Demonstrates the organization’s core values, exuding behavior that is aligned with the firm’s culture.
• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint, Outlook).
• Hands on experience with JIRA.

Nice To Haves

• Working knowledge of program/project management software such as MS Project is a strong advantage.
• Ability to learn any other appropriate program or software system used by the firm as necessary.

Responsibilities

• Lead agile cross functional team of Systems Developers, Software Engineers, Test Engineers, Operations, etc. from initial concept to deployment and production.
• Lead end-to-end delivery of enterprise-wide programs spanning technology, operations, and partner integrations in an Agile environment.
• Work closely with Product Owners to develop a multi-year plan to operationalize a technology support strategy, with key milestones, deliverables, and realization targets.
• Drive execution of solutions inclusive of concept definition, requirements validation, architecture specification, and governance compliance to our SDLC framework.
• Define program scope, goals, milestones, budgets, and resource plans; maintain rigorous governance throughout execution.
• Closely monitor project actuals to avoid cost overruns.
• Proactively identify and manage program risks, issues, and dependencies; develop and execute mitigation strategies.
• Manage multiple concurrent projects and workstreams with competing priorities in a fast-paced environment.
• Develop detailed implementation plans that include activities from multiple teams (business and technology).
• Meet complex program goals for product performance, quality goals, regulatory compliance requirements, cost, schedule, and development budget.
• Responsible for working with Product Management, Marketing, Designers, Developers, and Executive Management to define the product, solidify the business case, and identify funding requirements.
• Participate in negotiations involving Business Development and Legal.
• Directly responsible for creation and execution of departmental budgets and forecasts for applicable technology support functions.
• Serve as the primary liaison between technology teams, product owners, and executive leadership.
• Partner with business process owners to define roadmaps for continuous delivery of product enhancements.
• Facilitate governance meetings, project review sessions, and steering committee updates with directors and senior management.
• Produce clear, executive-ready status reports, program dashboards, and post-implementation reviews.
• Foster cross-functional communication and collaboration to ensure seamless operations and delivery outcomes.
• Champion process improvement initiatives; identify automation and efficiency opportunities to reduce manual effort and operational risk.
• Manage external vendor relationships, contracts, and deliverables to ensure accountability and performance.
• Allocate and optimize resources across programs based on priorities, schedules, and budgets.
• Mentor and develop team members ensuring adherence to governance, corporate, and departmental standards.
• Develop and negotiate SOWs in support of development and compliance efforts.
• Influence the continuously evolving Program Management Office (PMO) in support of critical business initiatives with consistent standards and governance.
• Support and enforce project management methodologies, best practices and reporting cadences across the team.
• Provide insight into the PMO Office on best agile practices and tools.

Benefits

• Award-winning industry expertise
• Award-winning industry competencies
• Award-winning insurers
• Highly differentiated culture that our clients consider an invaluable expansion of their business

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Associate degree