IT Strategies Group employs a team of developers, designers, sales professionals and administrative staff. Everyone in the organization is customer focused and is proud of the products they help produce. We know the tremendous value we can bring to our clients’ organizations and are always here to help our clients’ best utilize our products and services to maximize their potentials. We learn from our clients every day and are always looking for feedback we can implement.

Leadership Team


Craig Sienema - Chief Executive Officer / Co-Founder

Craig is a serial entrepreneur with extensive experience in the insurance and financial industries. Having been an independent adjuster and working many storms including Hurricane Wilma and Ike, Craig is keenly aware of the needs of the insurance industry, particularly dealing with large volumes of claims and catastrophes. Craig has also been extensively involved in the Deepwater Horizon BP oil spill disaster having assisted many victims and firms processing claims with everything from claim support, software needs and even designing extensive funding programs with hedge-fund partners to allow clients access to much needed cash and other resources.


Michael Pidgeon - Director of Sales

Mike has over 20 years of Sales and Marketing experience in the insurance/technology industry. Mike is responsible for leading the Claim Ruler sales organization and growing the current client base of Claim Adjuster firms subscribing to its claim management solution. Prior to joining IT Strategies Group, Mike was a top sales performer at QQ Solutions as well as a Regional Vice President with John Hancock Life Insurance Company. During his career he has won numerous sales awards including Presidents Club and Sales Person of the Year. Mike is a proud graduate of Boston College High School and earned his Bachelor’s Degree in Business Administration from Framingham State University. In his free time Mike enjoys the South Florida lifestyle of the beach and boating as well as volunteering his spare time with local animal shelters.


Omar Collazo - Lead Software Developer

Omar is the Lead Developer at IT Strategies Group overseeing the development team for Claim Ruler with 9 years of extensive experience designing and developing software solutions.  Omar is an avid software developer with expertise in C#, JavaScript, .NET, and SQL Server 2014.  Majority of Omar’s experience has been developing software for the U.S. Army’s Special Operations Command where he was recognized by a Brigadier General for his work on a mission critical application.  Omar has earned numerous certifications throughout his career with his most recent being the Microsoft Certified Technology Specialist (MCTS) certification and the Oracle Certified Java Programmer (OCJP).


Wendi Allen - Lead Systems Analyst

Wendi oversees client implementation and system designs for Claim Ruler. She has worked as a programmer analyst for several years in all realms of the manufacturing industry including human resources, production, inventory tracking, purchasing, shipping, receiving, finance, accounts receivable, accounts payable, vendors, contracts, franchises, and sales.  She was the General Manager for a security company overseeing Florida operations.  She has a Bachelor of Science in Computer Information Systems and a Master’s in Business Administration.


ITSG and Claim Ruler are always looking to hire skilled professionals that align with our core values. We employ people in a variety of positions including sales, support, training, systems design, development and programming. If you feel that you would make a valued member of our team please complete the form below: