Brian Fleagle
3595 Edgewood Avenue, Fort Myers
Summary
Results-driven Project Manager with extensive experience leading complex initiatives, managing competing priorities, and delivering projects on time and within scope. Demonstrated expertise across all phases of project and team management, with a strong ability to lead by example and drive high performance. Known for building collaborative, effective teams and fostering strong stakeholder relationships to achieve strategic objectives.
Overview
2026
2026
years of professional experience
Work History
Project Manager
Tyler Technologies
Remote
2023 - Current
- Led training-driven SaaS implementations for municipal enterprise clients, ensuring rapid adoption and long-term success
- Designed and delivered structured onboarding and product training programs for diverse client audiences
- Partnered with Support, Implementation, and Product teams to standardize training materials and documentation
- Identified skill gaps and process inefficiencies; implemented improvements that reduced rework and escalations
- Served as primary facilitator for client-facing workshops, live training sessions, and knowledge transfer
Software Support Specialist
Tyler Technologies
Remote
2021 - 2023
- Served as escalation point for complex technical issues, using each case to improve training documentation
- Developed internal knowledge articles and troubleshooting guides to support team enablement
- Coached clients and internal staff on best practices, improving product utilization and satisfaction
- Collaborated cross-functionally to improve support onboarding and continuous learning resources
Implementation Consultant
Tyler Technologies
Remote
2018 - 2021
- Delivered facilitator-led onsite and virtual training sessions for enterprise municipal clients
- Created customized training plans aligned to client workflows and operational goals
- Led onboarding programs from kickoff through go-live, ensuring knowledge transfer and user readiness
- Built trusted advisor relationships by adapting training approaches to varied learning styles
Senior Implementation Specialist
Claritysoft
Remote
2016 - 2018
- Designed and improved client onboarding and training workflows
- Created scalable training processes supporting a 450+ client portfolio
- Delivered remote and onsite training sessions for enterprise clients
- Mentored team members and supported professional development initiatives
Major Account Advisor
Paychex / myStaffingPro
Lima
2015 - 2016
- Delivered advanced product training for large enterprise clients
- Served as trusted advisor, ensuring effective system adoption and utilization
- Mentored junior advisors and supported ongoing skills development
Education
Bachelor of Graphic Arts -
Wright State University
Dayton, OHSkills
- Training Program Development
- Learning & Enablement
- Professional Development
- Curriculum Design
- Facilitator-Led & Virtual Training
- Onboarding Programs
- Stakeholder Management
- Process Improvement
- SaaS & Technical Training
- JIRA
- Confluence
- Microsoft Dynamics
- Advanced Excel
Military Experience
Ohio Army National Guard, Alpha Company, 37th Special Troops Battalion, 06/2008, 12/2014, Soldier of the Year (2012)
References
References available upon request.
Timeline
Project Manager
Tyler Technologies
2023 - Current
Software Support Specialist
Tyler Technologies
2021 - 2023
Implementation Consultant
Tyler Technologies
2018 - 2021
Senior Implementation Specialist
Claritysoft
2016 - 2018
Major Account Advisor
Paychex / myStaffingPro
2015 - 2016
Bachelor of Graphic Arts -
Wright State University