Senior Managing Director

Witt O'Brien's

11d•Hybrid

About The Position

Senior Managing Director, Puerto Rico & US Virgin Islands Position Summary Witt O'Brien's is seeking an experienced Senior Managing Director to lead the Caribbean portfolio, with primary responsibility for our Puerto Rico and US Virgin Islands operations. This position reports to the Chief Commercial Officer and will provide strategic leadership across disaster recovery, infrastructure resilience, emergency management, and federal recovery programs in the Caribbean region. The ideal candidate will have led large-scale programs for clients in Puerto Rico, the US Virgin Islands, and other Caribbean jurisdictions, with demonstrated expertise in federal funding mechanisms (CDBG-DR, HMGP, FEMA Public Assistance programs) and complex stakeholder environments. This individual will be accountable for portfolio performance, client satisfaction, business development, and strategic growth of the Caribbean service lines while ensuring consistent delivery of technical excellence and financial performance. The Senior Managing Director will oversee multiple concurrent programs valued at $50M+, lead cross-functional teams across construction, engineering, project management, disaster recovery, and emergency management disciplines, and serve as the primary strategic and operational leader for all Caribbean market activities.

Requirements

Minimum 15 years in executive or senior leadership position within Emergency Response, Disaster Recovery, or related federal/government consulting services
Preferred background with consulting firm and/or Federal, State, or Local Government agency experience
Minimum 10+ years' experience managing Public Assistance and/or disaster recovery programs and funding sources, including FEMA Public Assistance, CDBG-DR programs, HMGP, FTA-ER, FEMA-ER, and related federal recovery mechanisms
Demonstrated expertise in Puerto Rico and/or Caribbean recovery programs and stakeholder environments
Proven experience identifying emerging business trends and successfully executing business plans to exploit new market opportunities in recovery and resilience sectors
Demonstrated experience driving significant business growth with documented revenue expansion
Experience managing large-scale infrastructure programs ($25M+) in complex, multi-stakeholder government environments
Excellent leadership and strategic business skills with ability to lead teams of 20+ professionals across multiple disciplines
Proven ability to inspire, motivate, and develop high-performing teams while representing the company effectively in public and executive forums
Demonstrated experience collaborating with cross-functional colleagues and working effectively with federal, state, local, and international stakeholders
Experience presenting complex information to diverse audiences including government agencies, elected officials, and executive leadership
Strong analytical skills and ability to synthesize complex information and data into actionable business intelligence
Deep expertise in federal disaster recovery and emergency management frameworks, particularly as applied in Caribbean contexts
Ability to understand, interpret, and apply federal regulations, FAR requirements, Stafford Act provisions, and agency procurement procedures
Knowledge of Puerto Rico and USVI specific regulatory environments, including local government structures and procurement practices
Experience managing contractual obligations, scope management, and potential COI situations
Ability to develop systems of accountability for achieving results while continuously improving performance expectations
Ability to monitor external factors and market conditions while maintaining internal strategy focus and executing critical priorities
Demonstrated ability as an inclusive, collaborative leader who builds coalitions and maximizes value across diverse teams and stakeholder groups
Experience managing P&L, budget development, and staff utilization across multiple concurrent programs
Strong prioritization and time-management skills with ability to balance competing business development, operational, and strategic demands
Excellent oral and written communication skills, including ability to develop compelling proposals, executive summaries, and stakeholder communications
Bachelor's degree in relevant field from accredited college or university (or equivalent: two years of experience in assigned technical discipline may be substituted for one year of education, up to eight years)
Relevant professional certifications and training in emergency management, disaster recovery protocols, or federal grant administration highly preferred
Active knowledge of FEMA, federal procurement, and Caribbean regulatory requirements
10+ years managing federal grant programs and complex infrastructure projects valued at $25M+
Proven experience working with government agencies, municipalities, utilities, and institutional stakeholders
Ability to self-direct, manage time effectively, and prioritize multiple complex initiatives
Willingness to work extended hours as necessary to meet business development and program implementation goals
Ability to plan and manage development and maintenance of multiple concurrent client accounts
Proficiency with Microsoft Office Suite (Outlook, Word, Excel, PowerPoint) and project management tools
Ability to understand, interpret, apply, and explain federal regulations, procurement procedures, and agency policies
Ability to establish and maintain working relationships with government agencies, community organizations, and service providers
Ability to effectively develop, supervise, and manage multiple programs and diverse staff
Ability to coordinate complex program activities with other departments and external government agencies
Ability to work successfully with socio-economically and ethnically diverse populations in Caribbean contexts
Excellent verbal and written communication skills for individual and group interactions
Ability to negotiate, resolve problems, and manage conflict among stakeholders
Willingness to work non-standard hours, weekends, and potentially deploy on short notice as required

Nice To Haves

Advanced experience in Puerto Rico and/or US Virgin Islands markets
Leadership background with emergency management consulting firms
Track record of successful Caribbean-focused business development and market expansion
Familiarity with public-private partnership and resilience-focused funding mechanisms
Experience with international development or disaster response in Latin America/Caribbean region
Graduate degree in relevant discipline (business administration, emergency management, public administration, engineering)
Established relationships with Puerto Rico and USVI government agencies and institutional stakeholders
Track record of successfully managing organizational transitions and growth in recovery markets

Responsibilities

Develop and execute strategic growth plan for Caribbean portfolio, determining market opportunities and implementation strategy to achieve revenue and profitability targets
Identify new markets and service areas for portfolio expansion, with focus on Puerto Rico public/private infrastructure, PREPA, school systems, and other institutional clients
Develop and execute account targeting, capture, and development plans aligned with overall company strategic objectives
Oversee all business development activities and capture strategy for Caribbean market, including proposal development and client relationship cultivation
Establish and maintain strategic relationships with key government agencies, elected officials, and institutional stakeholders across Puerto Rico and USVI
Provide overall strategic and operational leadership for Caribbean portfolio, including all current and future programs
Develop strong client relationships and maintain thorough understanding of program objectives, team dynamics, client cultures, and solution requirements
Apply consulting expertise to determine appropriate technical and operational solutions to complex client challenges
Build and lead integrated teams of professionals across disciplines (engineering, project management, construction, emergency management) to execute program deliverables
Oversee delivery of large-scale infrastructure and recovery programs on-time and within budget
Manage P&L, staff utilization, and financial performance across portfolio to ensure targets are met and profitability objectives achieved
Liaise with clients, elected officials, government agencies, and other external stakeholders to represent company interests and support client success
Serve as primary contact and thought leader for technical matters, providing subject matter expertise in proposal responses and strategic consultations
Collaborate with executive leadership and clients to write, refine, and implement strategic action plans
Ensure consistent delivery of high-quality services through cross-departmental collaboration and strong internal and external communications
Oversee management of sub-contractors, workforce assignment, and project supervision within larger organizational structures
Provide leadership and oversight to team members, ensuring team is aligned with organizational goals and individual performance expectations are clear
Mentor and coach team members to support professional growth and development
Ensure compliance with all laws, rules, policies, procedures, and regulatory requirements
Track complex project plans and budgets across portfolio, identifying process improvement opportunities
Address performance issues in timely and constructive manner, providing support and guidance as needed
Manage work environment and project supervision for sub-contractors and workforce assigned to specific programs
Maintain comprehensive understanding of contractual obligations, scope requirements, and potential COI situations
Raise COI and scope concerns to appropriate levels of leadership when necessary
Monitor external market factors and regulatory changes while maintaining strategic focus and executing business priorities
Ensure all portfolio operations meet federal requirements, audit standards, and compliance obligations
Prepare executive presentations and summaries as needed for leadership briefings and stakeholder communications