Program Manager

The Baldwin Group is an award-winning entrepreneur-led and inspired insurance brokerage firm delivering expertly crafted Commercial Insurance and Risk Management, Private Insurance and Risk Management, Employee Benefits and Benefit Administration, Asset and Income Protection, and Risk Mitigation strategies to clients wherever their passions and businesses take them throughout the U.S. and abroad. The Baldwin Group has award-winning industry expertise, colleagues, competencies, insurers, and most importantly, a highly differentiated culture that our clients consider an invaluable expansion of their business. The Baldwin Group (NASDAQ: BWIN), takes a holistic and tailored approach to insurance and risk management.

What Are We Looking For

We are looking for a natural leader who thrives in complexity and ambiguity. The right candidate is someone who takes ownership, builds trust across organizations, and has the discipline to drive programs across the finish line without losing sight of quality, budget, or stakeholder needs. This role has high visibility and interfaces with various levels of program leadership; therefore, you must be equally comfortable presenting to a C-suite audience as you are rolling up your sleeves alongside your project teams. Ability to adapt quickly to shifting priorities with a continuous improvement mindset is a must in everything you do.

The ideal candidate brings strong technical fluency, strategic management skills and a demonstrable track record of delivering large-scale programs on time and within budget in an agile environment.

About the Role

The Program Manager will lead a multi-million-dollar, multi-workstream program within our vast and growing portfolio which requires end-to-end execution of complex, cross-functional initiatives across our insurance operations, technology, and partner ecosystem. This high-impact role will drive strategic initiatives from concept to delivery and serve as the connective tissue between executive leadership and execution teams. As Program Manager, you will be engaging with Product Owners to assess and prioritize direct customer feedback while driving execution via mature Agile practices. Experience in standard SDLC in an Agile environment is essential.

The Program Manager should have a sharp business mind and a proven ability to strategize and implement high-level program initiatives. The ideal candidate will be an excellent leader and will have experience in directly or indirectly managing and coaching staff of different disciplines to produce results in a timely manner. The goal is to ensure that all programs deliver the desirable outcome to our organization. The successful candidate must be able to make frequent trade-offs between business targets and projects and/or operational performance.

Key Responsibilities

Program Leadership & Delivery

• 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.

Stakeholder Engagement & Communication

• 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.

Technology & Process Improvement

• 8+ years of progressive experience in program management, portfolio management, or senior project management roles within financial services, insurance, or a similarly regulated industry.
• Champion process improvement initiatives; identify automation and efficiency opportunities to reduce manual effort and operational risk.
• 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.
• MBA (preferred) or bachelor’s degree in business administration, Information Technology, or a related field.
• Thorough understanding of PCI-DSS requirements and assessment practices. Candidates must be familiar with PCI controls and be able to apply PCI standards into the product development life cycle.

Vendor & Resource Management

• 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.

PMO Development & Standards

• 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.

Required Qualifications

• Master’s degree in business administration or information technology.
• Certified Scrum Master (CSM) or Certified Scrum Product Owner (CSPO).
• Experience managing large-scale compliance or regulatory programs (e.g., PCI, IAM, data governance).
• Scum agile methodologies implementation experience.
• Experience with software development best practices including Scaled Agile, TDD and Continuous Integration; a track record of applying these methodologies.

Knowledge, Skills, & Abilities

• 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).
• 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.
• Hands on experience with JIRA.

IMPORTANT NOTICE:
This position description is intended to describe the level of work required of the person performing in the role and is not a contract. The essential responsibilities are outlined; other duties may be assigned as needs arise or as required to support the organization. All requirements may be subject to reasonable accommodation to applicants and colleagues who need them for medical or religious reasons.

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The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.