Higher education outreach and engagement often occurs through student volunteering. Student organizations are one understudied and undertapped mechanism that facilitates such connections. We examined the experience of student leaders of student organizations that promoted volunteerism among their members. The mixed-methods study included a survey (n = 26) and follow-up interviews (n = 5). We found that participants’ organizations were highly involved in the community and that participants gained valuable leadership skills in this role. We also found that participants had relatively little insight concerning the community partners’ experience of the collaboration. We identified sampling as a unique challenge for this theoretical population and, in the discussion, provide considerations and recommendations for future scholars.