Joshua D. Whitley
Joshua D. Whitley
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    • Ty Whitley
    • Mary Kathryn Whitley
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    • Home
    • Experience
    • Expertise and Education
      • Expertise & Competencies
      • Education & Certification
    • Professional Memberships
    • More
      • Ty Whitley
      • Mary Kathryn Whitley

  • Home
  • Experience
  • Expertise and Education
    • Expertise & Competencies
    • Education & Certification
  • Professional Memberships
  • More
    • Ty Whitley
    • Mary Kathryn Whitley

Professional Experience

FLEXEC Advisory, LLC

President & Principal Consultant and Strategic Advisor

Jacksonville, FL | 2025 – Present                   

  

 As the President and Principal Consultant & Strategic Advisor for FLEXEC Advisory, I work at the intersection of executive leadership, technology, and risk, partnering with boards and C-suites to steer organizations through transformation with clarity, speed, and confidence. My advisory role is equal parts strategist, technologist, and trusted confidant, helping leaders unlock growth while safeguarding resilience.

  • Executive Partnership & Board Advisory: Provide senior leaders with actionable insight on technology, organizational change, and risk posture. Shape decisions that balance shareholder value, resilience, and long-term competitiveness.
  • Artificial Intelligence & Emerging Tech: Translate hype into strategy. Guide organizations in harnessing AI, automation, and next-gen technologies responsibly ensuring regulatory alignment, ethical adoption, and measurable impact.
  • Organizational Transformation & Change Leadership: Architect and execute enterprise change programs, reshaping operating models, culture, and governance to enable agility in volatile markets.
  • Technology, Cyber & Physical Security: Deliver holistic security advisory, integrating cybersecurity, data protection, and physical security into a unified resilience strategy that matches today’s hybrid risk environment.
  • Financial Services & Beyond: Leverage deep expertise in financial services while advising cross-industry executives on digital modernization, regulatory complexity, and market disruption.
  • Global & Geopolitical Awareness: Help leaders anticipate how geopolitical shifts, ESG mandates, and societal expectations impact technology, risk, and organizational strategy.


I thrive in the boardroom and the war room alike, helping organizations not just prepare for what’s next, but actively shape the future.


Past Experience

Triad Financial Services, Inc.

Chief Information Officer | Chief Technology Officer

Jacksonville, FL | 2022 – 2025


As CTO, and subsequently CIO, I led enterprise-wide technology transformation—modernizing legacy systems, driving digital innovation, and enabling rapid business growth.


I spearheaded a multi-year digital transformation initiative that overhauled core software and infrastructure, including launching new partner and customer portals, developing advanced Power BI analytics, and architecting a modern cloud-first environment. These efforts positioned the company to achieve its goal of doubling annual funding while enhancing scalability, performance, and data-driven decision-making.

My leadership extended across cybersecurity, software engineering, infrastructure, data and business intelligence, enterprise architecture, and production operations. I directed a comprehensive cybersecurity and compliance program, overseeing information and physical security, change management, and annual SOC 1 / SOC 2 certifications.


I managed multimillion-dollar budgets and vendor ecosystems exceeding $10M annually, optimizing technology investments, negotiating key contracts, and aligning resources with business outcomes. I also guided the strategic selection and implementation of enterprise software and hardware, building a cohesive technology roadmap that transitioned the company to a full cloud/SaaS operating model.

By introducing AI-driven tools and cloud automation, I empowered teams to work smarter and faster while ensuring 24/7/365 reliability of mission-critical systems. My focus on collaboration, efficiency, and innovation consistently turned technology from a cost center into a growth engine.

Step Up for Students

 Senior Director of IT Solutions

Jacksonville, FL | 2020 – 2022


As Senior Director of IT Solutions, I led major technology modernization efforts—transforming legacy systems into scalable, cloud-based platforms built on Microsoft Azure. My focus was on simplifying the technology landscape, reducing custom development, and creating a foundation for growth through automation and digital transformation.


I strengthened cybersecurity and compliance frameworks, conducting current-state assessments, developing new security policies and procedures, and leading SOC 1 / SOC 2 audit programs to successful completion. I oversaw technology delivery across software development, QA, enterprise architecture, data/BI, and production support, ensuring alignment with strategic business goals.


I managed program budgets across multiple cost centers and directed vendor management initiatives, including contract negotiations, SOW development, and resource allocation. I also guided the evaluation, selection, and implementation of enterprise-wide software and cloud solutions, crafting the roadmap for the company’s migration to a full cloud/SaaS infrastructure.


Key initiatives included the Epicor ERP migration and integration with the SQL data warehouse and CRM systems (Salesforce, HubSpot), leveraging Power BI and SSRS to deliver advanced analytics and operational insights. When needed, I stepped in with hands-on technical leadership—engineering, scripting, and developing in .NET Core, C#, and PHP—to drive momentum and ensure quality outcomes.

Synovus Bank (Now Merged w/ Pinnacle Bank)

Director of Technology, Specialty Services

Columbus, GA | 2017 – 2020


As Director of Technology for the Specialty Services division, I served as the technology lead across multiple subsidiaries, driving transformation programs that modernized platforms, strengthened security, and aligned IT strategy with business growth objectives.


I led the strategic shift from legacy, on-premise systems to scalable cloud solutions (IaaS, PaaS, SaaS), expanding digital capabilities and improving operational agility. My role included oversight of cybersecurity and physical security programs—developing policies, managing audits, and ensuring compliance with industry and regulatory standards.


I directed large-scale modernization efforts, including the integration and upgrade of the Black Knight Loan Origination System (LOS) and the enterprise-wide implementation of the Empower LOS management platform. Alongside these initiatives, I managed departmental budgets exceeding $15M and led diverse teams spanning engineering, operations, and program management—focusing on performance, growth, and delivery excellence.


Vendor management and strategic sourcing were key elements of my leadership, ensuring contracts and partnerships aligned with technology modernization goals. I also administered core enterprise systems including the Salesforce CRM suite and SAP ERP ecosystem, enabling seamless data flow and supporting enterprise-wide efficiency and insight.

CAN Capital

 Vice President of Technology

Kennesaw, GA | 2015 – 2017


As Vice President of Technology, I led global technology operations spanning software engineering, infrastructure, and production support—managing teams of 75–100 professionals across the U.S., Costa Rica, and India. My focus was on enabling scale, speed, and security through digital transformation and cloud adoption.


I architected and administered the organization’s AWS cloud environment (EC2, IAM, ELB, S3, RDS, ElastiCache, SNS), supporting web presence, data warehousing, and disaster recovery capabilities. This transformation modernized the company’s infrastructure and established a more resilient and flexible foundation for growth.


I also drove cybersecurity advancements, implementing secure coding standards, auditing and performance tools (New Relic, SolarWinds, Splunk), and hardened configurations across multi-platform environments (Linux, Citrix, Oracle, and Windows in AWS/Azure). These initiatives significantly improved security posture and operational reliability.


My leadership extended across enterprise systems and customer-facing platforms, including ERP and CRM implementations (Latitude, Salesforce, HubSpot). I provided hands-on technical direction in software development (.NET, C#, SQL, PHP, JavaScript) and deployment automation (GitHub, CircleCI, Docker, Heroku), ensuring rapid delivery and quality outcomes.


In parallel, I managed enterprise application support for VOIP, collections, risk, and financial systems, while integrating analytics and marketing automation tools (Google Tag Manager, Optimizely, Marketo) to enhance digital engagement and performance visibility.

Synovus Bank (Now Merged w/ Pinnacle Bank)

Senior IT Manager – Production Application Engineering & Support | IT Manager – Digital Banking

Columbus, GA | 2013 – 2015


As Senior IT Manager, I led enterprise-scale application engineering and support across 60+ critical systems, including Salesforce, Kofax, Empower, Fiserv FIS, and ServiceNow. Overseeing more than 185 servers, I ensured operational stability, performance, and security for production environments supporting key business functions.


I strengthened cybersecurity operations through the integration of Akamai Cloud Security and enhanced security architecture collaboration. Leveraging enterprise monitoring and troubleshooting tools—such as SolarWinds, Dynatrace, Splunk, and AppDynamics—I improved visibility and proactive issue resolution across complex infrastructures.


A key achievement included leading the enterprise-wide implementation of the AppDynamics platform, transforming application performance monitoring capabilities. I also optimized release management and code deployment processes, streamlining delivery pipelines and improving production reliability.


Before stepping into the senior manager role, I directed digital transformation programs for both Commercial and Retail Digital Banking, overseeing the development and launch of next-generation web and mobile solutions for iOS, Android, and Windows platforms.


I led end-to-end design, planning, and testing for solution, infrastructure, and data architectures that supported the bank’s expanding digital strategy. As a subject matter expert for Fiserv Corillian and Mobility platforms, I played a pivotal role in modernizing the institution’s digital banking experience—driving usability, performance, and customer engagement through innovative technology solutions.

Cicero Inc. (Now SMS Alternatives Inc.)

 Implementation Manager / Lead Architect

Cary, NC | 2010 – 2013


As Implementation Manager and Lead Architect, I directed large-scale integration programs focused on call center optimization—enhancing workflows, computer telephony integration (Avaya/Cisco), analytics, and single sign-on (SSO) across both mainframe and distributed environments.


I led comprehensive program planning and execution, developing master project plans, managing cross-functional teams, and maintaining close alignment with client stakeholders. My role encompassed contract negotiations, resource management, and budgeting to ensure successful delivery of enterprise technology initiatives.


Beyond program leadership, I oversaw the design and implementation of enterprise solutions integrated with major ERP platforms (Oracle, SAP, PeopleSoft) and business intelligence systems, delivering end-to-end visibility and operational efficiency. I also provided hands-on technical and cybersecurity expertise during solution deployment—bridging architecture strategy with secure, scalable execution.

Wachovia Bank (Now Wells Fargo)

 Licensed Financial Specialist

Columbus, GA | 2006 – 2007


As a Licensed Financial Specialist with Wachovia Bank, I provided comprehensive financial solutions across retail and commercial banking. Holding Series 6, Series 63, insurance, mortgage, and bank product licenses, I advised clients on investment strategies, insurance planning, and lending solutions tailored to their financial goals.


In addition to managing investment and loan portfolios, I supported daily retail banking operations and commercial lending activities—building strong client relationships through trust, financial insight, and service excellence. This role provided the foundation for my business acumen and customer-centric approach, which would later shape my leadership style in technology and digital transformation.

TSYS Inc. (Now Part of FIS)

Various Management and Individual Contributor Roles

Columbus, GA | 1997 – 2010


Over more than a decade in progressive technology roles, I built the foundation of my career in software engineering, business analysis, and technical leadership within the financial services industry. I served in multiple capacities—including Lead .NET Developer, Lead Business Analyst, Technical Manager (TS2 Platform Consulting), Associate Programming Manager, and various Programmer/Analyst roles—developing a deep understanding of enterprise systems, client consulting, and product delivery.


These years shaped my approach to technology leadership—blending hands-on technical expertise with strategic problem-solving, process improvement, and a focus on building high-performing teams. The experience provided the technical and operational grounding that would later fuel my success in large-scale digital transformation and executive technology leadership.

Copyright © 2025 Joshua D. Whitley - All Rights Reserved.


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