This document examines the first year of Jobs for the Future's Benchmark Communities Initiative (BCI), a 5-year effort to achieve the following: large-scale systemic restructuring of K-16 educational systems; involvement of significant numbers of employers in work and learning partnerships; and development of the infrastructure necessary to connect high schools, postsecondary educational institutions, and employers in a coherent system. Presented first are an overview of the BCI and its 5-year goals. Chapter 1 profiles the following BCI communities and their current/planned school-to-careers activities: Boston, Massachusetts; Jefferson County, Kentucky; Milwaukee, Wisconsin; North Clackamas, Oregon; and Philadelphia, Pennsylvania. The following system-building challenges and strategies are examined in chapter 2: using school-to-careers to drive school restructuring; engaging sufficient numbers of employers; and building the infrastructure to connect school and work. Goals/plans for the next 4 years of the BCI are outlined in chapter 3. Appended are the following: site information about the benchmark communities; Boston compact mission/goals statement; model for Jefferson County Public Schools magnet career academy; characteristics of Milwaukee's school-to-work schools; Oregon's certificate of initial mastery for grades K-10; summary of Philadelphia's Children Achieving action plan; and benchmark communities initiative application information. (MN)