Headmaster was founded on a handshake in 1985 by general partners Paul Dorrance and Ben Schmitt. The partnership coincided with their development of Headmaster© administrative software for schools for management of records such as transcripts, attendance, and report cards. In 1987 the company launched its first version of Grademaster©, software for use by teachers for classroom administration. To better serve our school clients, the business expanded to include computer hardware sales and network consulting.

In 1993 "Montana's HeadMaster network" was recognized by U.S. News & World Report (December 6 p 56-60, 62-63) for its contribution to "Pioneering the Electronic Frontier". The acknowledgment came as a result of the network's ability to deliver curriculum (distance learning) to remote regions of the Northwest. One of the courses approved by the Montana Department of Health and created by a Montana RN was for nurse aide training and evaluation. In 1991, in accordance with OBRA regulations, the state of Montana contracted with Headmaster to begin certified nurse aide (CNA) testing and certification using our in-house developed Testmaster© software and a bank of CNA test items developed by Montana subject matter experts, including those pioneers in the distance learning program. Approval to test, and contracts for testing of CNA's in Oregon, North Dakota, and South Dakota came in 1999.

Ohio CNA testing and Ohio lead abatement testing came on board in 2001. At that time it seemed appropriate to the founding partners that their business name change to reflect the diversity of their services, and that the company formally be structured as a limited liability partnership. Thus, D&S Diversified Technologies LLP dba Headmaster LLP was born. 2001 also saw the opening of our Eastern region office in Findlay, Ohio.

Tennessee, Delaware, and Idaho CNA testing contracts were won in 2002. Iowa and Utah have since contracted to use our software and/or test bank for CNA testing in their states, and Mountain States Line Constructors based in Utah contracted to use our software for linesman test item development for testing in a five state region.

In 2004 we rolled out WebETest©, a suite of wildly successful applications for on-line test content development, on-line test scheduling, and on-line delivery of test content. That same year saw the 5600 sq ft expansion of our Findlay, Ohio office along with the creation of D&S Training Center LLP. In addition, the Helena, Montana office moved into a newly renovated headquarters.

2005 welcomed Arizona, Vermont, New Hampshire and Oklahoma to our Nurse Assistant testing family.

In 2006-7 Ohio, Montana, Arizona, Oklahoma and Arkansas began item development and testing of medication aides/assistants/technicians.

2008-9 we developed and added Facility Administrator testing in Idaho.

2010 saw the addition of New Jersey where we provide content and manage skill testing for four test disciplines along with our strategic competency testing partner PSI Services LLC whose knowledge test centers deliver the knowledge portion of the tests. These disciplines are Nursing Assistant, Personal Care Assistant, Medication Assistant and Facility Administrator testing.

In recent years we have focused on expanding the use of the Internet for all facets of the testing process; from registration of candidates upon enrollment into a training program, to testing, to a complete web-based registry management system, with online employer verification for required renewal processes. Developement on TestMaster Universe begins in 2011.

2013 we added X-ray Technician and Direct Service Worker testing in Ohio and 2013 saw Paul Dorrance buy out Ben Schmitt's interest in the Companies. Ben is now hired as a consultant as needed..

In 2015 the Nevada Nursing Assistant Competency Testing Contract was added.

In 2018 the Wisconsin Nursing Assistant Competency Testing Contract was added.

In 2020 the Arkansas and Missouri Nursing Assistant Competency Testing Contracts were added.