Creating Transparency for prospects and Efficiency for institutions

At DegreeSight, we understand the challenges institutions face when working with the 70% of students who bring credit with them on day one. Our mission is to streamline the credit evaluation process, thereby allowing universities to focus on what really matters – supporting and educating their students in a personalized way – and less on paperwork.

Leadership Team 

David Cook

Founder, CEO

During the 2008 Financial Crisis, David experienced a significant mix-up with his transferred course credits that almost cost him $75,000 in scholarships from Baylor and a job offer from Hewlett-Packard, very similar to another advising mistake which had caused his brother to leave the university the very year prior. This challenge inspired David to establish DegreeSight, a technological innovation aimed at preventing such costly mistakes for students.

With 15 years of experience as a lead engineer turned product manager focused on digital transformations, David built and now steers DegreeSight with a commitment to enhancing clarity and efficiency in higher education. His mission is simply this – to increase the percentage of students who graduate and finish on time.

David lives in Austin, TX with his wife and 3 sons.

Greg Baker


Greg has served higher education since 1988 as a former Resident Assistant at the University of Maryland, College Park while studying Resource Economics and Management Information Systems.  His enthusiasm to bring technological solutions to improve and enhance the higher education experience has been his passion for over 30 years.  Greg has served higher education institutions with companies including Special Teams, Inc., Blackboard, the Institute for Professional Development, CTS and DegreeSight.

Greg joined DegreeSight’s Founder and CEO David Cook in January with the goal to help as many higher education institutions as possible with the most impactful tool currently serving prospective students, transfer students, registrars and enrollment teams.

Chelsea Bassett

Vice President of Industry Relations & Strategy

Chelsea is a strategic leader in higher education with a passion for increasing equity and access for all learners. With experience from multiple public state schools, Chelsea has worked in several areas including strategic planning, student success, advising, and admissions. After a 15-year career in public higher education, she joined the National Student Clearinghouse, and helped create technology solutions to increase learner mobility with more effective data exchange options.

As a first-generation college student and after working with thousands of students from various demographics, Chelsea recognizes transparency and efficiency in the college process is desperately needed to combat the convoluted processes that hinders higher education success. Not only do these challenges drive up cost, but it also makes college accessible to only those who can navigate the system. DegreeSight is a mission-driven company looking to change this reality and transform some of the most inefficient facets of the education system.

Chelsea lives in Texas with her husband and spends most of her spare time watching soccer, cheering on the Huskers, and spoiling their two pups.

Chelsea graduated from the University of Nebraska with a Bachelor of Arts degree majoring in History with a minor in English followed by earning a Master of Education in Higher Education Administration.

Josh Weinstein

Josh Weinstein

Director of Implementation & Customer Success

With over 15 years of dedicated experience in software implementation and project management, Josh Weinstein is a seasoned professional who excels in optimizing complex processes to enhance customer experiences. 

He’s managed highly dedicated teams of project managers, business analysts, and implementation specialists in many industries including courier/distribution, virtual call center, manufacturing, education, and hr/compliance.

Josh couldn’t be more excited to leverage his expertise to ensure DegreeSight offers the smoothest and most efficient implementation process and continued white-glove support beyond going live.  In addition to implementation and customer support, he’ll lead our tech support team to ensure our clients problems are quickly resolved and documented.

His commitment to excellence extends beyond the workplace, enjoying a fulfilling life in Tempe, AZ, with his loving wife, Rebecca, and his two precious daughters, Olivia (8) and Lexi (5).

Josh graduated Magna Cum Laude in Computer Information Systems from Arizona State University.

Our Business Development and Education Advocacy Team

Shayne Boelter

Shayne Boelter

Regional Vice President

Shayne Boelter is a seasoned business development professional specializing in cross-organization collaboration, strategic planning and growth. Shayne is passionate about delivering results and building lasting client relationships with over ten years of experience exceeding customer expectations.

Shayne and his wife of eleven years, Kayla, are proud parents of their 8-year-old son and a 6-year-old daughter. Their family is completed by a rambunctious miniature golden doodle all residing in Fort Worth, TX. Shayne and Kayla are deeply committed to their local church community where they actively serve on various leadership teams, including the Men’s and Women’s Ministry, Children’s Ministry, and the Preaching team.

Shayne attended Liberty University and Biola University.

Tim Gilbert

Tim Gilbert

Regional Vice President

Tim is a highly experienced leader in higher education, with a career spanning over 23 years. His journey in higher education began at South Dakota State University, which gave him valuable insights into the inner workings of academic institutions. He then transitioned to working with various EdTech companies, where he held diverse roles ranging from project management, leadership, and sales.

Throughout his career, Tim has been actively engaged with key stakeholders across different departments within higher education institutions. This includes enrollment management, admissions, financial aid, registrar’s office, dining services, security, and academic departments. His ability to connect with and understand the needs of these various departments has been a defining aspect of his career.  This empathy-driven perspective allows him to develop and implement solutions that help institutions operate more efficiently and provide a better overall experience for students.

Tim’s career has been dedicated to improving higher education by facilitating the adoption of technology and best practices that enhance the educational journey for both staff and students. His wealth of experience and his focus on collaboration with key stakeholders, make him a valuable asset in the higher education space.

Tim graduated from South Dakota State University earning a Bachelor of Science in Psychology.

Dave Stout

Regional Vice President

Dave’s overview might be missing, but with over 20 years of experience supporting Higher Education, we can assure you one thing above all else – Dave understands the challenges institutions face with implementing complex technologies. 

JesAnne Bouchard

JesAnne Bouchard

Registrar and Higher Education Advocacy Manager

Champion of Higher Education Reform and Advocate for Registrar team members.

JesAnne is a dedicated advocate for positive change in higher education. Her tireless efforts to address the systemic challenges facing higher education drives her passion for change. JesAnne’s long history working with non-profit organizations and educational institutions has helped have a significant impact in both sectors.

Her journey towards education reform began early in her career when she recognized the logistical deficiencies within the higher education system. It was this realization that ignited her passion for creating a better future for students, faculty, and administrators. With a deep sense of empathy and a keen eye for efficiency, JesAnne set out to revolutionize the way higher education operates.

JesAnne’s unique perspective and dedication stem from her hands-on experience serving multiple registrar’s offices in state and private higher education institutions. Her firsthand knowledge has fueled her commitment to finding practical solutions to alleviate the burdens faced by these unsung heroes of academia.

JesAnne’s community spirit and dedication is reflected in her frequent appearance at local sporting and theater events in Kansas where she lives with her two dogs. She also regularly partakes in Bingo at a local cidery, and produces a true crime podcast.

JesAnne earned an Associates Degree in Liberal Arts from Butler County Community College, a Bachelor of Science in Sociology with a Criminal Justice concentration from Newman University and a Master of Science in Justice Studies with a certificate in Terrorism and Homeland Security from Southern New Hampshire University.

Technology and Data Team


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