The Jupiter Observing Velocity Experiment (JOVE) is a solar-powered technology demonstration of rapid flight to outer solar system targets, performing a flyby of the Jovian magnetosphere 30 days after launch. This is achieved using a magnetic drag device to accelerate with the solar wind plasma. This “Wind Rider” propulsion system can potentially also decelerate against the Jovian plasmapause dawn eddy, to enable Jupiter orbital insertion in future missions. The 16U cubesat bus contains an array of scientific instruments to record the plasma parameters from the vicinity of the spacecraft, with principal measurements coming from a SPAN-I ion velocity sensor. A description of the propulsive mechanisms and supporting subsystems is included, as well as trajectory simulation results derived from solar wind measurements over the past two solar cycles. The objectives of the JOVE technology demonstrator design include: 1) verify Wind Rider stability and control, 2) characterize loss mechanisms in the solar wind, such as resistive losses in the plasma, as well as the magnetic field transient interaction time, 3) operate onboard instruments to measure velocity and direction, to enable precision navigation on future science missions, and 4) characterize the Lift-to-Drag ratio of the plasma magnetic field. (The lift force enables lateral course control and maneuvering within the solar wind.) Applying existing scientific data from Voyagers and other deep space probes into new engineering models is critical for enabling new insights about Wind Rider propulsion. That, in turn, enables more science to be performed in a shorter amount of time, across the Jovian system and beyond. Policymaking recommendations from the Practical Interplanetary Propulsion (PIP) Study are discussed towards the end of the paper, for ways to encourage use of this technique in other deep space destinations of interest to the scientific community. This class of propulsion system enables SmallSat missions to a wide variety of outer solar system targets, opening up a range of previously unreachable science opportunities.