The software, Rjenda, has been used by some independent schools, including Castilleja, Sacred Heart, Woodside Priory, Mercy High School in Burlingame and University High School in San Francisco.
It allows teachers and administrators to enter assignments and school events into a database and ultimately creates a picture at the individual student level of workload and tests.
"So often we work anecdotally 'My son or daughter spent 'x' number of hours on this assignment,'" Winston said in an interview this week.
"My hope is to provide Paly and our community with some data so we can start having conversations around what's reasonable and what's excessive."
Rjenda describes itself as a tool to "manage student workload and stress."
Founder and CEO Ranvir Wadera said his goal is to help teachers, students and parents "better manage student workload and stress, and facilitate meaningful discussion based on real data."
The software allows teachers to see their students' schedules and workloads from other classes, and students and parents to view their assignments and tests.
Winston's initiative at Paly coincides with concerns about homework loads particularly at the high school level across the school district.
A close look at homework policy is likely to be recommended as a district-wide "focus goal" for 2011-12, based on discussion at a school board retreat this past June.
"We are working on the best way to develop a homework policy task force, principal and teacher work first and then sunshining, student input, etc.," Superintendent Kevin Skelly said this week.
"At this point I can only say that we are working and thinking about this."
Skelly is scheduled to present his recommended "focus goals" for 2011-12 at a board meeting this coming Tuesday, Aug. 23, and a board vote is expected Sept. 13.
At the June retreat, school board members expressed concerns about "test clumping" the problem of exams from different classes falling on a student at the same time.
Members said they may adopt a specific district-wide homework policy as a nudge to drive change.
But board member Dana Tom warned that, "If it feels like a top-down directive, you won't get much compliance (from teachers)."
At the time, Skelly said the faculties at Paly and Jane Lathrop Stanford Middle School already had taken steps to examine homework policy.
To launch its partnership with Rjenda, Paly has turned over test data from last year, Winston said.
"We've exported it, and they're going to input it so we can see what students' lives looked like last year," he said. "It's pretty revolutionary."
Winston acknowledged that, so far, Rjenda depends on teachers and administrators to enter data on tests and assignments.
"In math, everything gets inputted it gets pulled out of the grade book," he said. "If you're an English teacher, it might be when an essay was due. The system takes it and presents it in a simple, colorful way.
"We're going to have last year's data, and I'm confident it will be solid."
Winston said he plans to ask his department heads to use Rjenda "live" this year.
"As they're moving through the year they'll input when they're giving assignments, and we'll get a glimpse of what students' lives look like. It won't be a full picture.
"It would be cool if we asked students how much time (assignments) actually took them on task. Rjenda is interested in this."
At Castilleja, Rjenda has been used by teachers since 2009 "for major assessment scheduling, to reduce conflicts for students throughout the academic year," spokeswoman Dana Sundblad said.
"The idea is to reduce stress and create a more balanced workload calendar for the girls by allowing faculty to see what's been scheduled by others and to collaborate on grade-level (especially in middle school) scheduling more easily," she said.
Wadera said most of his current customers are independent schools but that he's excited to work with Paly.
The company, which Wadera launched in 2008 after working at Oracle, Business Objects and Hyperion Solutions, charges an annual subscription based on the number of students and size of school.