“The Boston Fed’s Working Cities Challenge (WCC) was developed to advance leadership and collaboration in New England’s smaller, postindustrial places. The Boston Fed, in partnership with a team of private-, public-, and philanthropic-sector leaders, offered competitive grants of up to $700,000 to teams from smaller cities in Massachusetts that committed to working collaboratively across sectors on initiatives that would improve outcomes for low-income residents.” This article distills “key lessons learned from the first rounds of participating cities in Massachusetts [that] are now informing the planning process for the cities that follow and the regional initiative as a whole.”