In her first term, she persuaded the management-consulting firm McKinsey & Company to produce, at no cost, a strategic plan for the Palo Alto school district. Four years later, that plan continues to guide board decision-making.
Caswell also has spent much of her personal time promoting the Developmental Assets, a youth-wellness framework adopted by the school district and other local groups following a string of student deaths by suicide in 2009 and 2010.
She sees the "asset-building" program as useful not just for teen mental health but also for pushing students toward genuine learning.
"Our district is really good at putting out students with high test scores. We're really good at sending our kids to excellent post-high-school options. But our goal needs to be a little different than that," she said.
"We need to create leaders for the next generation — they need to be learning because they're curious, because they're challenging themselves to learn more, not just for the A grade."
Caswell said the asset-building aligns with her role as a board member of the nonprofit Youth Community Service, which works in Palo Alto and East Palo Alto to foster youth leadership through service.
"If our kids aren't going to be the leaders for the next generation I don't know whose are," she said.
"I think it's important for us to invest in that kind of (community service) learning."
In her first board term, Caswell parted company with the majority in two controversial votes: a 3-2 decision in 2009 to adopt the K-5 mathematics textbook "Everyday Mathematics," and the 3-2 vote in May 2011 to revamp the 2012-13 and 2013-14 academic calendars to begin the school year in mid-August so as to end the first semester before the December holidays.
She served as president of the board from 2010 to 2011.
On the current debate over high school guidance counseling, she backs the process now in place and says "it would be a huge shame" to undermine the district's culture of site-based decision-making by having the board specify to Gunn how to organize its program.
"There's value for some things to be managed from the top — managed, not mandated," she said.
"But we have a culture here that we've hired professionals and told them they can do their best work, and we'll give them goals and hold them accountable.
"If we mandate things from the top and it feels like people are being micromanaged I worry that some of our best people will leave."
As a former manager in technology companies, she said she found "if you told people how to do the details of their jobs they stopped making decisions themselves and started becoming passive-aggressive."
But Caswell admits that the board "could do a better job at clarifying and communicating goals (to school staff) and how we're going to hold people accountable."
Caswell earned an MBA and spent 14 years in the business world, first on Wall Street and later in Silicon Valley, before devoting herself to volunteer work.
She was president of the Palo Alto PTA Council, a Girl Scouts leader, and sits on the board of the Palo Alto Art Center Foundation in addition to Youth Community Service.
Among a long list of community activities she lists on her resume, she includes that of "lice checker" at Duveneck Elementary School.
Caswell says the remarkable level of diversity in Palo Alto schools is not always well recognized.
"We have kids whose parents never went to high school and who come home and have no books in their home. We have kids who have every opportunity but are not engaged. We have kids with every opportunity and are engaged. We have kids with special needs, and we have kids from every country in the world.
"There are so many different variables that reaching every kid where they are is a big challenge, but that is really our responsibility," she said.