Summary
Overview
Work History
Education
Skills
Timeline
Executive Board and Community Leadership
OperationsManager

Matthew C. Pierson

Tampa,FL

Summary

High performance and proven leadership success in business strategy, people management and organizational growth, sales and operations, and project management, with 15+ years of experience excelling in the corporate risk management industry. Outcomes-based leader and expert in team building across specialized functions for skillful execution of data-driven strategy and innovative enterprise initiatives. Military veteran leader of action, highly proficient in complex problem solving, dynamic cross-functional teams and improving measurable results for exceptional growth and adaptive team development.

Overview

2026
2026
years of professional experience

Work History

Major, U.S. Marine Corps Reserve

United States Central Command
- Current
  • Currently serving as a Staff Operations Officer at U.S. Central Command Headquarters (TS/SCI security clearance)
  • Completing graduate level capstone course for U.S. Marine Corps Command & Staff College for promotion to the next rank of Lieutenant Colonel (expected graduation in May 2025)

Director (Leader)

The Baldwin Group (NASDAQ: BWIN)
04.2021 - 03.2025
  • Market leader for middle market corporate insurance advisors delivering strategic and financial consulting for innovative employee benefit program design and employer health plan optimization
  • Achieved 151% sales performance to goal for 2024 new business sales, leading and coaching a team of senior partner advisors daily with a combined book of business of $5.8M in annual sales revenue
  • Responsible for organic sales growth to C-Suite customers by advisors of all levels in the firm, including senior partners, while also recruiting new advisor talent for the future growth of the firm
  • Executive leadership collaboration with national leaders across specialty divisions and business segments for process improvement and comprehensive, measurable financial results for clients

Lead Consultant

USI Insurance Services
04.2017 - 04.2021
  • Lead advisor at top 10 global insurance brokerage firm, managing senior consulting teams for mid-market employer benefit plans, group health plans and corporate risk management programs
  • Led implementation of analysis and regulatory compliance to $10M in human capital programs
  • Designed solutions using data analytics to reduce employer health plan costs by 10-20% through implementing innovative programs, including M&A due diligence resulting in 10% plan savings
  • Achieved 100% client retention, awarded for top performance by the USI PEAK program

Lead Consultant

Willis Towers Watson (NASDAQ: WTW)
09.2011 - 04.2017
  • Lead advisor at top 3 global insurance brokerage firm, managed senior consulting teams for mid to large employer group health and benefit plans, M&A projects, and corporate risk management programs
  • Primary leader for cross-functional expert consulting teams managing over $20M in corporate insurance and human capital programs, generating approximately $800K in annual revenue
  • Led delivery of compliance and underwriting expertise resulting in financial protection; designed and implemented innovative benefit programs increasing employee engagement activity by 30%
  • Selected from 200 applicants, distinguished performance award by Exceptional Producer Council

Vice President (Leader)

MDI Holdings, Inc.
12.2008 - 09.2011
  • Spearheaded operations for data analytics in start up division, managing 15 project managers, analysts, software developers and healthcare experts in building new data analytics and claim solutions
  • Designed new scalable technology workflow process to streamline operations, leading software development teams and increasing claims flow operational efficiency by over 20%
  • Grew business development expansion territory for state-of-the-art employer human capital data analytics, developed and spearheaded competitive marketing position for six states exceeding expectations and resulting in a $1M business to business sales pipeline in 6 months
  • Recruited from over 400 applicants for competitive leadership program, promoted 5 times

Captain

United States Marine Corps
05.2003 - 12.2008
  • Planned, executed and supervised high risk strategic missions around the world as a platoon commander and officer-in-charge, reporting to senior military officers and working with international units
  • Operationally led and supervised highly skilled groups ranging from 30 to 130 people, with accountability for $1-3M inventories of U.S government property and highly sensitive military equipment
  • Awarded for exceptional leadership and heroic performance in multiple overseas deployments
  • Selected (less than 1% of Marines) and achieved top performance in completing high attrition advanced level training schools for elite U.S Marine Corps Force Recon (Amphibious Reconnaissance School, Airborne School, Combatant Diver School, SERE Survival School)

Education

Master of Business Administration -

University of Florida
Gainesville, FL

Master of Science - Risk Management and Insurance

Florida State University
Tallahassee, FL

Bachelor of Arts - Pre-Law

Miami University
Oxford, OH

CEBS Professional Designation -

The Wharton School & IFEBP
University Of Pennsylvania

Skills

  • Goal-oriented leadership in fast-paced environments
  • Executive perspective and decisive problem-solving
  • Identifying high impact areas of growth opportunity
  • Operational risk management with data-driven metrics
  • Accelerating top results form high performing teams
  • Inspiring teamwork and influencing key stakeholders
  • Process-driven management for growth and scalability
  • Cross-functional communication and collaboration

Timeline

Director (Leader)

The Baldwin Group (NASDAQ: BWIN)
04.2021 - 03.2025

Lead Consultant

USI Insurance Services
04.2017 - 04.2021

Lead Consultant

Willis Towers Watson (NASDAQ: WTW)
09.2011 - 04.2017

Vice President (Leader)

MDI Holdings, Inc.
12.2008 - 09.2011

Captain

United States Marine Corps
05.2003 - 12.2008

Master of Business Administration -

University of Florida

Master of Science - Risk Management and Insurance

Florida State University

Bachelor of Arts - Pre-Law

Miami University

CEBS Professional Designation -

The Wharton School & IFEBP

Major, U.S. Marine Corps Reserve

United States Central Command
- Current

Executive Board and Community Leadership

  • The Boys & Girls Clubs of Tampa Bay, Board of Directors and Executive Committee (Safety Chair)
  • MacDill Air Force Base, Honorary Commander (927th ARW)
  • Leadership Tampa Bay, Alumni (former committee member)

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Matthew C. Pierson