The evolution of technology innovation by businesses using the Internet is transforming and reshaping the nature of inter-organizational commerce and relationships. This case proposes the evolution of technology innovation by a popular family-owned business situated in Vermont. It investigates the technology innovation at Dakin Farms applying the systems development life cycle methodology. The case analyzes phases of IT implementation and its influence on inter-organizational systems and relationships that in turn affects employees’ morale and culture. The case contributes to research, practice, and education.