HAROLD CUTLER
Pembroke Pines,FL
Summary
Experienced insurance and transportation risk professional with a deep understanding of DOT and FMCSA regulations. Over 25 years in the insurance industry, including 4+ years specializing in trucking insurance and fleet risk management. Proven track record as a motivated Sales Manager, leading teams to exceed sales goals, expand territories, and secure new accounts. Former diesel/truck instructor and corporate trainer for Caterpillar engines with multiple certifications, including Truck Analyst Instructor. Former Safety Manager at a CAT dealership, with expertise in compliance, fleet monitoring, and driver qualification processes. Host of a trucking podcast aimed at helping carriers avoid compliance pitfalls and navigate insurance challenges. U.S. Coast Guard veteran.
Results-driven professional with focus on risk management and mitigation strategies. Known for delivering impactful solutions and fostering collaborative team environments. Highly adaptable to evolving challenges with keen ability to analyze complex data and ensure regulatory compliance.
Overview
25
25
years of professional experience
1
1
Certification
Work History
Transportation Risk Specialist
Prestige Trucking Insurance
11.2021 - Current
- Built and managed a $3M+ book of business through outbound sales.
- Delivered insurance solutions tailored to fleet clients (20+ trucks).
- Provided compliance guidance and mentorship to internal teams.
Financial Registered Representative
New York Life Insurance Company
11.2017 - 12.2020
- Designed personalized financial strategies after client assessments.
- Launched and managed multi-channel marketing campaigns.
- Delivered excellent service, ensuring long-term client relationships.
Managing Broker
Stockbridge Insurance Group
05.2010 - 11.2017
- Led Medicare Advantage/Supplement sales division.
- Recruited and trained agents to exceed performance goals.
- Created staff development and communication initiatives.
Exclusive Financial Consultant
Allstate Financial Services
02.2006 - 05.2010
- Developed goal-based financial plans and risk profiles.
- Collaborated on initiatives to increase market presence.
- Maintained full compliance with industry regulations.
Partner / Broker / District Manager
Stockbridge Consulting Group
02.2002 - 02.2006
- Managed a 52-agent sales team, increasing revenue by 27%.
- Surpassed annual sales goals by 23%.
- Oversaw market development and proposal strategies.
Financial Advisor
Merrill Lynch Wealth Management
02.2000 - 01.2002
- Achieved 127% of a $10M annual production goal.
- Provided investment and asset management guidance.
- Consistently ranked among top performers.
Education
Florida International University
Miami, FLSkills
- Transportation Risk Management & FMCSA Compliance
- Trucking Insurance & Fleet Programs
- Strategic Sales & Business Development
- Property, Casualty, Life & Health Insurance
- Financial Planning & Retirement Products
- Team Leadership & Agent Training
- Customer Retention & Relationship Building
- Compliance, Hiring, and Safety Oversight
- Effective Communication & Negotiation
- Operational risk management
- Enterprise risk management
- Compliance monitoring
- Risk analysis
- Market risk analysis
Certification
- 2-20 General Lines (Property & Casualty)
- 2-15 Life, Health & Variable Annuities
- Series 6 Securities License
- Multiple Caterpillar Certifications (Truck Analyst Instructor)
Awards
6× President’s Club Award – Insurance Sales, Triple Crown & Platinum Award – AFLAC, AFLAC Fame Award: Hired 27 agents in Year 1; surpassed goal by 15%, Summit Qualifier – New York Life (First Year), Scoutmaster & Cubmaster – Boy Scouts; Brotherhood – Order of the Arrow, Youth Soccer Coach: 2× State Champions, 2× National Invitations
Timeline
Transportation Risk Specialist
Prestige Trucking Insurance
11.2021 - Current
Financial Registered Representative
New York Life Insurance Company
11.2017 - 12.2020
Managing Broker
Stockbridge Insurance Group
05.2010 - 11.2017
Exclusive Financial Consultant
Allstate Financial Services
02.2006 - 05.2010
Partner / Broker / District Manager
Stockbridge Consulting Group
02.2002 - 02.2006
Financial Advisor
Merrill Lynch Wealth Management
02.2000 - 01.2002
Florida International University
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