Common-Sense Leadership for Westport’s Schools
Jodi Harris
Jodi has spent nearly two decades strengthening Westport’s schools, including terms as PTA president of Saugatuck Elementary and Staples High School. A proud parent of a Staples graduate and a current Staples student, Jodi has been a tireless advocate and fundraiser for our public schools, championing Staples Tuition Grants during Covid and serving on the combined Bedford Middle School/Coleytown Middle School board during the complicated mold remediation. Prior to that, Jodi worked at HarperCollins Children’s Books as editorial director and has authored more than 40 books for young readers.
Stephen Shackelford
Stephen and his wife have raised four children in Westport’s schools —two Staples graduates, one current Staples student, and one at Coleytown Middle. From 2019 to 2023, he represented our community on the RTM, earning a reputation for thoughtful, collaborative leadership. Professionally, Stephen is a lawyer at Susman Godfrey. He served as co–lead counsel for Dominion Voting Systems in its historic defamation case, securing a $787.5 million settlement from Fox News in 2023. He brings that same dedication, integrity, and persistence to his commitment to Westport’s students and families.
Endorsements
“Jodi and Stephen worked incredibly hard this summer, at a time when school is often the last thing on people’s minds, to engage over 400 registered Democrats (and approximately 200 independents) and secure their place on the ballot because they believe the ‘big ticket’ issues must be revisited and prioritized. I have no doubt that when they revisit these, they will do so with openness to perspective from our community and the kind of engaged listening they always employ. That’s the kind of Board of Education our families deserve to bring our children into a complicated decade of academic and professional change.”
Gery Grove, WPS parent
“My partners and I at Susman Godfrey support Stephen not because we will agree with everything he does on the Westport BOE — and certainly not because we want to influence anything in Westport — but rather because we know him to be a person of extraordinary dedication, diligence, intellect, and honor. And we know him not just as a superb lawyer, but also as a wonderful husband and father, who wants to serve Westport for all the right reasons and to genuinely help your community.”
Neal Manne, partner (and former managing partner), Susman Godfrey
“As a deeply invested parent of two graduates and a current Staples junior, I am proud to enthusiastically support Stephen Shackelford and Jodi Harris for the Westport Board of Education. Having known Stephen for years from the soccer sidelines, I greatly admire his passion and integrity. My career in education constantly reminds me how privileged we are to send our children to Westport schools. Yet recent challenges have highlighted the critical need for stronger community engagement, transparency, and accountability. I know Stephen and Jodi will champion these values and work constructively with everyone, regardless of political affiliation, helping our schools thrive and keeping Westport a great place to learn and live.”
Jack DeWitt, WPS parent
“I’m writing to implore Westport residents to vote for Stephen Shackelford for the Board of Education (BOE). I served with Stephen on the RTM and he is one of the smartest, talented, and truly decent individuals that I had the pleasure of working with both there and over the course of my life. And he’s humble so let me highlight some of his accolades. Stephen went to Harvard and then Harvard Law School, graduating first in his class. He then clerked for Justice Stephen Breyer of the Supreme Court of the United States. Subsequently, Stephen has made a name for himself as one of the most skilled trial attorneys in the area.
“I would support Stephen’s candidacy for any office. He is one of the rare people in life that is both smart enough to figure out the solution to any issue and has the diplomatic skills needed to bring that solution to fruition. But Stephen is also uniquely qualified to serve as a BOE member given his prior RTM experience, his four children that have gone through the Westport Public School System, and his vast knowledge of its workings as spouse to a PTA co-president.
“Our BOE will be facing numerous complicated challenges over the next four years, from redistricting to artificial intelligence and beyond. I trust Stephen Shackelford to make decisions on those issues on behalf of my children and hope he earns your vote as well.”
Christine Meiers Schatz, Westport parent of four, former RTM member, and former member of Board of Education Special Committee
“I have worked at both Fox News and CNN, and in this year’s Board of Education election, I’m voting for individuals, not hand-picked party people. Jodi Harris and Stephen Shackelford are individuals with a proven record of service to our town. I trust them both to be strong, independent voices on a BOE that hasn't had nearly enough of that in recent years. They’re also the only candidates offering good, concrete ideas for improving things in our school district, in a range of areas. I encourage anyone reading this to vote for both of them.”
Dave Briggs, national broadcaster and WPS parent
“I’m proud to support Jodi Harris and Stephen Shackelford for our Board of Education. Over their many years of service, they have consistently demonstrated integrity, compassion, prudence, and a deep commitment to putting students and families first. I trust their leadership to keep our schools strong and ensure every voice in our community is heard.”
Tracy Benton, WPS parent
“After a series of disheartening and disillusioning acts by the current Board of Ed, we are thrilled to endorse and vote for Stephen and Jodi. We have known Stephen for about five years and could not be more impressed by his passion, intelligence, and commitment to the Westport community.”
Jonathan and Amy Hochhauser, WPS parents
“I’m proud to endorse Stephen Shackelford and Jodi Harris for our town’s Board of Education. Their integrity, honesty, and unwavering commitment to doing what’s best for our children make them the kind of leaders we need. They listen, they care, and they will always put students first. I trust them to make thoughtful, informed decisions that reflect the values of our community.”
Nicole Neil, WPS parent
“Jodi Harris and Stephen Shackelford are both deserving of a spot on the BOE. They discuss specific issues/problems openly and candidly, and I appreciate that, their desire for transparency, and their willingness to admit what this board has done well and where improvement is desperately needed.”
Carrie Howard, WPS parent and former PTA president
“I am proud to endorse Jodi Harris for election to the Westport Board of Education. I have had the honor and pleasure of working with Jodi in a volunteer capacity over the last nine years, including most recently when we served as co-presidents of the Staples PTA. In her volunteer work at Saugatuck Elementary, Bedford Middle School, and Staples High School, Jodi has proven herself as a leader who cares about and advocates for all of our students. Jodi is kind, sincere, dependable, and responsive. She will question our administrators when necessary and bring integrity and transparency to the BOE.”
Elena Caggiano, former PTA president; WPS parent
“I know Stephen Shackelford listens carefully, does the hard work, has a balanced, even temperament, and comes up with cogent workable solutions. He knows how to lead. I am grateful he cares so deeply about Westport that he is once again stepping up to devote his time to improve the Town. He is far and away one of the most impressive public servants I have ever seen grace the Westport local government — both from an intellectual and character standpoint.”
Kristan Hamlin, former Westport RTM member (8 years of service) and former DTC member (17 years)
“Jodi Harris and I have worked together for 10-plus years in PTA. She is a born leader. She is thoughtful and listens to all sides, but most important, she puts the children of the Westport Public Schools first when making decisions. She gets results, advocating for projects such as the new swim scoreboard at the high school and the Senior Tradition of the Senior Walk. This new tradition is so special: The high-school seniors visit their grade schools, and it is a wonderful memory for our high-schoolers to take with them on their next journey. Jodi was able to accomplish so much because her children are a product of the Westport Public Schools. She can see what needs assistance and then listens to parents, teachers, administrators, and students and then helps to make it happen. I think that Jodi would make a wonderful addition to the Board of Education. I endorse Jodi Harris.”
Michele Carey-Moody, former PTA president
“I’ve known Stephen for nearly a decade now. He is a creative thinker and a wise counselor, an excellent and passionate lawyer, as well as a fundamentally decent and honorable human being. I have seen firsthand how he brings to his work a refreshing combination of independent thinking and humble and respectful open-mindedness to others’ viewpoints — and a willingness to change his position when confronted with new facts. I consider Stephen to be a genuine, ethical leader who cares about others and is always principled in his decision-making. I have no doubt Stephen will bring all this to bear in service to the Westport BOE.”
Dov Seidman, founder and chairman of the How Institute for Society and LRN; author of “HOW: Why HOW We Do Anything Means Everything” (Wiley)
“I worked closely with Stephen at GE and GE Capital. He is smart, principled, does his homework, and never shies away from challenges. He fights in all the right ways for what he believes is right but also listens to, considers, and respects opposing viewpoints — a balance that is rare but so needed these days. As a longtime resident of Westport, I’d be thrilled to have Stephen join our Board of Education, where he will serve the families of Westport with dedication, passion, and distinction.”
Alex Dimitrief, longtime Westport resident and former General Counsel and President of the Global Growth Organization at GE
“I met Jodi when I joined the Staples PTA Executive Board. She impressed me right away with her vast knowledge of Staples and the Westport school system at large. It was clear to me that as PTA president, she was passionate about what was in the best interest of the students and teachers and held that as her guiding principle. She is a tireless advocate for program enhancements and new opportunities and experiences for students and staff alike. She is the type of person who is always looking to leave things better than how she found them. She is no-nonsense, not afraid to ask the hard questions, and a great listener who values consensus building and actively seeks out opinions on all sides of an issue. I am so grateful to now be able to call Jodi a friend and can’t wait to vote for her for the Westport Board of Education in November.”
Maria Mulvehill, former PTA president; WPS parent
“Westport and the Board of Education can do better. Jodi Harris and Stephen Shackelford are our chance to make that happen.”
Chris Grimm, former RTM member
“My dad was a longtime English teacher at Staples and the president of the Westport Education Association. I graduated from Staples. My wife, our daughter, and our son graduated from Staples, too. I’ve talked with Stephen and Jodi and read their detailed proposals. I have no doubt they will take Westport schools in new directions, and I endorse them wholeheartedly.”
Rick Leonard, communications executive
“Stephen and Jodi will ask the tough questions and make informed decisions that will better our community, not embarrass it. It is indeed time for a change.”
Nikki and Andy Laskin, Westport residents and parents of two recent Staples graduates
“I’ve put two kids through our Westport public schools, and I know how important it is to have BOE members who are committed to our kids and also to bringing their own independent judgment to the work and listening to both students and parents on what matters. That’s why I wholeheartedly endorse Stephen and Jodi.”
Paloma Bima, WPS parent
“We strongly support Stephen and Jodi’s run for Westport’s Board of Ed. As true forward thinkers, who are not afraid to challenge the status quo, they each bring a fresh perspective and can definitely be counted on to stand up for what is right. With children in Westport’s public schools, they understand the importance of, and are perfectly suited for, the position.”
Merri and Adrian Mueller, WPS parent
“As a college student who attended Westport Public Schools, I am proud to support Jodi Harris and Stephen Shackelford, two individuals who offer thoughtful, principled leadership and deeply value due process. Jodi's two decades of service and Stephen's extraordinary legal mind make them the ideal candidates to restore accountability and integrity to the Board of Education.”
Alex Laskin, Staples ’23, Cornell ’27
“Stephen is amazing! No matter what side you’re on, having a BOE member who is a stand-up character is the most important thing!”
Isabelle Ricks, Staples ’22 and Sacred Heart University ’26
Where We Stand
One of the biggest misperceptions we’ve heard about our candidacy is that this race is about replacing the superintendent.
It is not. This election is about leadership at the Board of Education, and the future of Westport schools. It’s about whether the BOE can govern confidently and proactively, working with our superintendent to overcome blind spots and protect our public schools.
Another major misperception has to do with “endorsed” candidates.
The Westport Democratic Town Committee endorsed 2 candidates for the Board of Education, highlighting their vetting process. In August, one of those candidates withdrew from the race. The other candidate, who is an appointee on the current board, has access to party-provided resources like funding, voter data and campaign coordination.
We did not receive the 72-member DTC endorsement, so we don’t have access to party resources. But we wouldn’t trade our route to the ballot for anything. We earned our spot by securing the handwritten, in-person signatures of more than 440 registered Westport Democrats. That grassroots effort represents real people valuing choice beyond party-appointed candidates, and it allowed us to hear directly from residents about their most pressing concerns.
This choice between party endorsements and grassroots-driven candidates is playing out across the entire race. While 5 candidates have been endorsed by official political committees (including 4 Republicans), the other 3 candidates for the BOE are challenging that system: the two of us, who petitioned our way into the race, and Robert Harrington, who is running as a write-in candidate after the Republican Town Committee shut him out. We believe Westport deserves a choice that places people over politics.
Another misperception is that protecting special education requires direct personal SpEd experience. While one of us has unique personal experience, the real issue is systemic. We’ve heard from many families about their enormous, costly challenges securing the services their children need.
Though some experiences are positive, this uneven access to support has festered for years. The board needs independent voices willing to challenge this status quo and its high costs to both families and taxpayers. We will be those voices.
This brings us back to the larger misperception: that this race is about one person, one event, or one group of stakeholders. It is not.
It is about whether the BOE has the strength, skills and independence to set direction, manage risk, and provide effective oversight. When boards lose confidence in their own role, they invite chaos. When they fail to lead, they leave the administration and community vulnerable to missteps.
Healthy debate is not dysfunction; it’s how good governance works. The real danger comes when boards avoid deliberation, shy away from transparency, or operate without clear priorities.
That vacuum leads to confusion and unnecessary conflict. It also creates an opening for louder, more ideological voices to dominate the conversation — voices that want to bring national culture wars into local classrooms, question professional educators, and erode support for public education itself.
Between us, we bring deep experience in law, communications, negotiation, strategic planning and community leadership. We are not running to dismantle the system, but to strengthen it — by restoring accountability, elevating standards of leadership, and ensuring decisions are made transparently.
The relationship between a Board of Education and a superintendent is a partnership, not a rubber stamp. The superintendent’s role is multifaceted. He has numerous managerial responsibilities (including ultimate responsibility for a large staff), but he also should be the district’s visionary leader, challenge assumptions, and propose bold initiatives to move our schools forward.
The board’s role, as the elected voice of the community, is to ensure that vision is thoroughly vetted, financially sound, and easily measured for maximum impact.
Finding this balance requires mutual respect, transparency, and a shared commitment to excellence. But effective oversight is not passive agreement. A board that simply “gets out of the way” abdicates its primary responsibility to the voters and taxpayers who elected them. Unfortunately, we’ve seen this happen all too often.
Too many board meetings have featured major proposals approved with minimal questioning from the majority, despite valid concerns raised by the community and even other board members. This lockstep approach is not healthy governance. It fails our students, our educators, and ultimately our superintendent.
A case in point is the prolonged debate over the Staples cellphone ban. While we support the goal, the process revealed a flaw in the system.
For over a year, the administration advocated for the ban without presenting a detailed implementation plan or budget, despite repeated requests from parents, teachers, and students. A proactive board would have insisted on answers to crucial questions: What is the impact on curriculum? What technology alternatives are needed? What are the costs? What success metrics will we use to determine effectiveness? Instead, these questions were largely deferred. A board exercising proper oversight would have demanded a complete plan before the discussion could advance, ensuring a smoother, more successful rollout.
This pattern of reactive governance has other consequences. A lack of motivated questioning and failure to demand transparent processes has preceded controversial personnel decisions and costly lawsuits that have consumed district resources and eroded public trust.
Rigorous oversight is not about micromanagement; it is about foresight. It’s about asking the hard questions, and insisting on actual answers before moving forward, so we can achieve the best outcomes and avoid negative consequences in our schools and community.
A well-functioning board is also one that brings issues to light that the administration may have missed, or not properly prioritized. Part of the board’s job, as the democratically elected officials responsible for our school system, is also to serve as a key point of contact for Westport voters (and other stakeholders) with concerns about our schools. We’ve heard too many stories lately of concerns being raised to the board and then completely ignored or minimized without any real explanation, let alone discussion.
Let us be clear: Our goal is not to obstruct, but to strengthen. We are running to be constructive partners. A board of independent thinkers, willing to engage in robust and respectful debate, will challenge the administration to bring forward its best, most well developed ideas.
True leadership welcomes accountability. We believe a better balance is possible. One where the board and superintendent work together, with healthy debate and transparent decision-making leading to superior results for our entire community and a restoration of trust. We are confident that we can work constructively with Superintendent Scarice to continue to accomplish great things for Westport’s schools.
The district’s budget must respect separate but distinct stakeholders: residents whose children currently attend the public schools and deserve the very best service and programming, and those who have watched their children graduate or who have moved to Westport for everything but the schools, and need to protect their most valuable asset (their home) and pay reasonable taxes.
To be sure, the $150 million annual budget for schools seems generous. But more than 80 percent of that is contractual: salaries and benefits for our hardworking teachers and school staff.
What’s left can’t begin to cover building updates, curriculum and program enhancements, and the modernization demanded of a 21st-century school system. It just can’t.
So despite their best intentions, the district and BOE are left playing Whac-a-Mole, repairing things here, replacing things there, often only after a problem has gone from bad to worse, instead of tackling the district’s needs in a truly holistic, top-down, forward-thinking approach.
A few examples: The Staples auditorium hasn’t been touched in more than 30 years. Much of it is original and over 60 years old. The lighting mechanism got stuck on the stage last spring, rendering the auditorium inoperable for 6 weeks.
The Staples football field was built for a population of around 1,400, and now we’re at 1,700 and climbing. The stands are too small, bent and even wobbly in sections. The “away side” is cramped, dark, and surrounded by brush. The sound system is broken, there is no handicapped access or seating, and there are no bathrooms.
What’s more, Staples has no working girls’ locker room. Girls’ teams change in hallway bathrooms.
And we all know what happened after Coleytown Middle and Long Lots were neglected … and now Coleytown Elementary is reported to be close behind.
Kings Highway has a basement gymnasium and cafeteria that don’t meet ADA requirements. Concerns abound within the special-education system. Additionally, the district remains woefully short on substitutes and paraprofessionals.
A facilities committee meeting — the first since January — was quickly scheduled just recently, in response to many of these growing concerns. But wouldn’t everyone benefit from year-round follow-through — not just during campaign season?
So how do we address buildings and staffing while remaining fiscally responsible, forward-thinking and adaptable? First, we have to identify issues that haven’t made their way to the BOE yet, and then we have to do the hard work of creating real budgets for dealing with all of them, so we can make intelligent trade-offs, in both timing and funding, across our whole portfolio of problems.
Second, we have to find the money to tackle these projects. One solution we propose for consideration is a public-private partnership in which the district would accept outside donations.
This hinges on the district — in concert with the First Selectman’s office — approving the consideration of features like naming rights. Imagine a capital improvement campaign that allows our cherished alumni, current families and future graduates to make meaningful financial contributions in exchange for a named brick, plaque, or even an entire structure? How else does a public school district — even one the caliber of Westport — find the vast funds that are absolutely necessary to fix up its crown jewels?
Of course, nobody has a monopoly on knowing where the problems lie, or what the best solutions are. Our doors are open to all stakeholders who are ready to flag problems and propose solutions, and that’s exactly how we will operate if you elect us — people with new ideas, new experiences, new connections, and renewed passion for our kids and their education — to the BOE.
Before going into what needs immediate attention, we want to call out what’s working: the dedicated teachers and staff of the Westport Public Schools and our generous force of parent volunteers. They all work together to support each other and, most importantly, the next generation of Westporters.
Simply put, the most important issue facing our schools is one of leadership. The Board of Education and the administration must use their roles and resources to address the concerns of every stakeholder. And they must do that efficiently, effectively, and transparently.
For some reason it is taking years to fix small problems, which become big problems, which in turn become seemingly intractable — and expensive — problems. In recent years, too many teachers and staff members have been held to a higher standard than the administrators they report to.
The administration’s role is to eliminate obstacles so our teachers and staff can succeed. The role of the BOE is twofold: to manage the superintendent, and to serve as the elected voices for our schools.
Yet in one meeting after another, the BOE is doing less and less to engage our superintendent in meaningful debate about what needs to improve and what he is getting right. If we don’t make smart decisions, we risk failing to attract the most talented educators and staff to our schools. Here are just a few recent examples:
Many elementary school teachers have desperately called for more paraprofessional support, yet last year’s budget proposal instead added additional assistant principals, expanding an already top-heavy organization without providing classroom support.
Additionally, a lack of substitute teachers means our educators are losing their prep periods to cover classes, a problem particularly noted at the middle-school level. The systemic issues extend beyond the classroom: A single overworked plumber services all 8schools, leading to long wait times for critical repairs. There are many more stories we don’t have room for here.
The School Climate Survey presented in September 2024 showed a troubling drop in student engagement. Where are the 2025 scores? Why haven’t they been presented? Parents and students deserve transparent reporting of the latest scores and a clear plan to address any issues. The north star for both the administration and the BOE is continuous improvement and a positive outcome for our students.
As board members, we’d take a different approach from that of many of the current members. The BOE must be proactive, not reactive, and be honest with our community. First, we’d directly engage with our teachers and staff. Do they feel adequately supported and respected? Why do they think hiring pools are shrinking so dramatically, and what changes do they think are critical for success in the classroom?
Next, we’d engage more purposefully with our students. For years the BOE has promised to survey Staples students for inside knowledge on their coursework, and to capture the pulse of student life — but it hasn’t happened. This needs to change immediately. Giving our students a voice and a forum for feedback is the least we can do. Good ideas can come from anywhere, and sometimes it’s as though our kids are actually the adults in the room.
It’s time for the BOE to stop making excuses, and start engaging and executing on solutions. We want to help move our schools from good to great — with transparency, accountability and accessibility at the forefront.
We need a board that is inclusive, not exclusive. We want to meet the needs of our students with the teachers, staffers, facilities and curriculum they deserve. And that starts with board members who understand and embrace the critical role they play.
Restoring Trust
Bring clarity, transparency, and accountability back to the Board of Education
Practical Solutions, Not Partisan Ones
Focus on common-sense solutions that unite, not divide, our community
Protecting Our Schools
Plan responsibly for long-term needs so every school is safe, strong, and supported
Putting Families First
Students, parents, and educators should guide decisions—not politics
News
The League of Women Voters of Westport Board of Education Debate 2025
Watch
October 30, 2025, by Dan Woog, 06880danwoog.com
“Where We Stand”: Board Of Ed Candidates Offer Final Messages To Voters
October 17, 2025, by Dan Woog, 06880danwoog.com
Roundup: Another Election Question, A New Westport League, New Handicap Spots …
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Vote for both on November 4th!
Early voting began October 20th
Paid for by Harris-Shackelford for BOE. Netta Levy, treasurer. Approved by Jodi Harris and Stephen Shackelford
