Over recent decades sponsorship has evolved significantly, in terms of an expanding range of sponsorship opportunities as well as an increased range of activation options. Where less significant development can be observed is in the area of sponsorship evaluation. This paper outlines a specific company case study focusing on a relatively new, but now well-established brand, which made a significant strategic choice in utilizing sponsorship for brand building, market penetration, and the acquisition and retention of consumers in an increasingly commodified service category in contrast to the strategic mix chosen by its main competitors. The paper provides a detailed focus on the management and evaluation of their sponsorship activity in one particular market. Following a brief introduction to the O2 brand and its international development, it will examine the brand's position in the Irish marketplace and the strategically chosen role for sponsorship in its armory of marketing options. It details the key strategic pillars, which underpin the approach to sponsorship as a set of beliefs that hold sponsorship policy and activation together. The challenge, in a mature market dominated by competition for market share, was to drive short-term sales while building long-term brand equity. The industry was experiencing a paradigm shift from “mobile operators” to “social networks” and the paper explains how the choice and activation of sponsorships sought to develop participative interaction with customers to promote emotionally driven loyalty. To make the brand the basis for differentiation the company chose a marketing mix weighted toward sponsorship and placed “participation” at the core of activation. The strategic choices involved regarding the balance of resources between paid-for media and sponsorship and in the latter case, between assets and activation, are explored. Two case studies relating to sport and entertainment sponsorship are detailed with particular reference to innovative and creative activation through social networks. The paper will outline the use of quantitative tracking measures as well as more involved measures in evaluating sponsorship performance. More specifically it will focus on the measurement of sponsorship performance and in particular on the various points at which measurement is brought to bear and the range of metrics—including softer measures such as sentiment analysis and social media conversations—utilized in this evaluation process. It will thus arrive at a comprehensive approach to measuring sponsorship effectiveness and demonstrate how results are translatable to monetary values.