When we started our journey building Measure, a contributor relationship management system, we thought we knew the path we'd take. While the concept was new, the two people involved had expertise building both communities and software. The path, it turns out, wasn't as clear as we expected. We knew Measuring communities effectively would be difficult, and would involve both code and people... but there was a lot we didn't anticipate. Travel with us on our journey as we explore how we approached this problem from the different perspectives of coder and consumer, and how this resulted in a smooth release but also some bumps along the way; how some questions went unanswered and some seemingly easy tasks turned out to be deceptively difficult. In this talk Stuart and Jeremy will share 6 lessons learned, and you'll leave with both a better understanding of how to evaluate your community and collaborate on building software.