Philip Cheshire



IT Executive & Architect.

Love what you do, do what you love. - Me

I'm a Northeast, FL based IT executive, software architect, developer and technologist leading teams creating effective and efficient software solutions for companies of all sizes around the globe. I deliver tangible, measureable results. Exceeding expectations is what I have built my professional reputation on.

Growing up, I've always had two loves: cars and computers. Realizing early in my college career that I was not going to become a professional race car driver, I turned to computers. I've always had a love of technology and I've had the great fortune to make a living doing what I genuinely love to do. My latest adventures have me leading an amazing team who help customers across the globe build better engaging digital experiences.

Outside of work, I am a husband and a novice racer. Once a month or so I take my beloved ///M2 to an autocross event where locally I'm known as the "tire slayer". Even outside my career, I'm a leader. As the chairman for volunteer organizations, I've worked with volunteers to ensure events were held in compliance so we all could enjoy what we love.


Years of IT Experience
across a myriad of industries.


Years of Management Experience
leading internal, vendor, and hybrid teams.


Successful Projects
delivered to customers since 2013.


Percent Success Rate
agile methodology conversions.


Let's change the status quo, together.

Project & Engineering Management / Board Member

I can provide scrum guidance and management, engineering and development management, or act as a member of your board to help steer your organization to success.

Software and Web Solutions

Whether is a simple site to take appointments or help with DNS records, or a full blown ecommerce and inventory management deployment, I can create or recomend solutions to fit your needs.


Have tons of data but can't make any sense of it? Are your web analytics not providing value? Let's go over your situation and determine the right path for your situation.

Technical Consulting

Do you need someone to just take a look at things? Perhaps in need of guidance or support for a large project? I got you covered.

Globably Available

Have passport, will travel. I don't confine myself to only business in the United States. Businesses across the globe are leveraging my services either directly or indirectly.


Let my resources of highly experienced graphic artist and designers take your vision to the next level.


My entrepreneurial spirit, natural leadership ability, technical competence, and the desire to learn has helped me gain skills that help me manage and deliver successful projects both professionally and personally.

Executive Leadership
Decisiveness Integrity Dependability Problem Resolution Team Building
IT Leadership
Agile / SCRUM & Historical / Waterfall Project Management Budget & Licensing Management Digital Experience Transformations Incident and Change Management DevOps, Continuous Integration & Delivery
Programming & Software Development
Java/J2EE & Associated Technologies/Frameworks (ie Spring, Maven, etc) Web Browser Technologies (HTML5, CSS3, JavaScript, etc) Model Driven & Test Driven Development Web Analytics Root Problem Determination
Cloud Adoption & Migration Container Adoption & Migration Serverless Computing RHEL/Linux, Unix, AIX, Microsoft, and Apple Operating Systems


With over 18 years of information technology experience, I have survived the rise and fall of several tech bubbles and have advised, consulted, or been employed by companies across all industries. This experience has provided me with a well rounded approach to all situations.


Proven information technology leader with over seven years of management and three years of executive leadership experience managing engineering teams who help customers across all industries from inception to post-launch and beyond.


Professional Experience

Asponte Technology

Asponte Technology, Inc.

Director of Engineering

Lakewood Ranch / Saint Augustine, FL

As a member of the executive team, I am responsible for the technical direction of the company and ensuring my team and our customers are successful. I represent Asponte Technology to our software partners and vendors, customers, and at technical conferences. I work hand in hand with my fellow executives to strategically align our business objectives, internal software usage, product offerings, and sales/marketing initiatives with the technical direction of the digital experience industry. Working directly with other executives, I oversee and mentor the engineering staff, and advise the executive team in all aspects of our business.

  • Acting Chief Executive Officer (CEO) pro tempore
  • Sales and Marketing team agile methodology adoption
  • Conceived, architected, and oversaw internal and customer product development
  • Container based development & Redhat OpenShift internal adoption and service offering development
  • Managed services LOB product improvements
  • Write and deliver employee evaluations
  • Instrumental in company direction and resource utilization during COVID-19 pandemic

Innovation and Mobile Practice Leader

This position entailed researching and implementing mobile, new and cutting edge technologies for us and our customers such as artificial intelligence and cognitive software. I mentored and sculpted junior and senior developers to become better consultants both with business interaction and technical skill. Between myself and my technical peer, we were positioned as the top guru's of the company.

  • Designated Chief Executive Officer (CEO) pro tempore
  • Conceived, architected, and developed internal software products
  • Engineering team Agile SDLC adoption

Solution Architect / Technical Lead

Responsible for architecting, implementing, developing, and leading projects based on IBM and Open Source software platforms both internally and for our customers.

  • Lead and mentored engineering peers
  • Installed and migrated software deployments
  • Provided custom coded solutions to meet customer requirements
Computer Sciences Corporation

Computer Science Corporation (CSC)

Software Engineer

Jacksonville, FL

  • SME and developer for IBM WebSphere Portal and Web Content Manager.
  • Performed code reviews and mentored other developers both on and off shore.
  • Team liasion for off shore management and team members
Kemper, A Unitrin Business

Kemper Corporation

Application Developer III

Jacksonville, FL

  • Portal and portlet applications developer developing JSR 286 portlets and portlet services for public portal and Agent facing portal utilizing IBM WebSphere Portal v6.1.5 and v7.0.0.2, IBM Web Content Management (WCM), jQuery, Dojo and Google JS frameworks, JMS, Web Services and Java 6.
  • Architected, designed and developed custom web metrics solution for portal sites across multiple portal implementations and domains.
  • Aided in architecting and primary developer for five corporate affiliate Websphere Portal v7.0.0.2 sites.
  • SME for portal development across all corporate affiliates.
  • Wrote and taught five day custom developed portal and portlet developer course.
  • Co-founder and co-leader of portal governance committee.
  • Mentored other developers and performed code reviews.


Application Developer III

Jacksonville, FL

  • Technical lead over new development for Marketing and Pricing IT Solutions Team
  • Developed JSR 168/286 portlets, portlet services, utility applications and web services for the Enterprise Portal.
  • Created and implemented development and deployment standards, guidelines and applications for portlet and web service developers.
  • Formed and led the Java Developer's Group meetings, mentored junior java developers, and performed code reviews
  • Conceived, designed and developed a customer facing portal for reward card holders and led the technical integration with 3rd party vendors.
  • SME and key resource for the enterprise portal upgrade, Vendor Portal implementation, and IBM Lombardi Business Process Modeling projects.
  • Utilized IBM Websphere v6/6.1/7, IBM Websphere Portal v6/6.1.5, JAX-RPC/JAX-WS, WS-Security, EJB 3.0, Ant, XMLAccess, shell scripts and IBM Rational Application Developer 7 & 7.5.
State Farm Insurance

State Farm Insurance

Systems Analyst

Bloomington, IL

  • SME for WebSphere Portal projects across multiple business units
  • Pushed architecture review of portlet services to an eventual approval
AFNI, Inc.

AFNI, Inc.

Software Engineer

Bloomington, IL

  • Designed, developed, and supported web based applications, web services, and portal services using IBM Rational Application Developer, IBM Websphere 6, IBM Websphere Portal 5.1, J2SE, JSP, JSF, SQL 2000, CSS, Apache Tomcat 4, JTDS JDBC driver, Linux, and ASP
  • Key developer in the migration of 50+ web applications and web services from Apache Tomcat 4 to IBM Websphere 6 and IBM Websphere Portal 5.1
  • Designed and developed modular automation application to automate the new hire and termination activites.


Bachelor of Science in Information Technology

Middle Georgia State University, Macon, Georgia

Professional Achievements

  • Presenter at several conferences
  • Book Reviewer for Packt Publishing: IBM WebSphere Portal 8: Web Experience Factory and the Cloud
  • Designed and built business process software designed for small business
  • Provided custom software solutions and IT department management for manufacturing company

Personal Achievements

  • Eagle Scout, B.S.A.
  • 1st Place SCCA Tire Rack National Tour E Street Prepared
  • Chairman for Buccaneer Region SCCA Jacksonville Solo
  • Chairman for Central Illinois Region SCCA Solo
  • Webmaster for Champaign County Sports Car Club
  • Champaign County Sports Car Club Spark Plug Award Receipient


Have a glimpse into my personal and professional life with these images and videos.

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  • Professional
  • Personal
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Saint Augustine, FL