Introducing Heather Calomese Our New President
Every great tour starts with a prologue, a short, revealing stage that sets the tone for the miles ahead. Since joining Five Keys in June, Heather Calomese has spent her first month exactly that way: listening, learning, and building relationships across every corner of the organization before setting her pace. From special education teacher to public policy, Heather brings her career in the classroom and education leadership to her new role as President of Five Keys.
Here’s what won’t show up on her resume: Heather was a professional volleyball player in Austria, (where she had to learn German to communicate), a journalist in New York and a competitive volleyball player in college. She’s remained a lifelong athlete ever since, these days logging serious cycling miles through the
Bay Area today.
That background shows up throughout her career in how she leads: the discipline of daily training, the mental toughness to hold her composure under pressure, the instinct to read a room (or a peloton) in real time, and a deep, personal understanding of what it means to be part of a team where every rider’s position matters. In her own words: “I don’t shy away from complexity. I plan to lead with courage and remain focused on advancing the mission with both conviction and humility, building the structures and capacity Five Keys needs to grow, without ever losing what makes Five Keys so special.”
As she steps into the role of President, here’s an introduction to the person behind the title, her path, her philosophy, and what she hopes the Five Keys community will know about her.
The Prologue: Why Five Keys, Why Now
Heather’s career in education leadership, including roles with the Illinois State Board of Education and the California Department of Education, has consistently been shaped by a belief in the dignity, potential, and humanity of every person. Five Keys, she says, was a natural next move: a chance to trade the isolation of state government work for something with more immediate, human impact.
“Throughout my career in education and public service, I have been drawn to organizations that believe deeply in the dignity, potential, and humanity of every person,” says the Oakland resident. “I’ve worked adjacent to the work that Five Keys does for my entire career. Being in public policy and state government is isolating at times, far removed from the individuals that it’s meant to impact. I was seeking a role that had a more immediate impact on individuals’ lives and I was also seeking to grow professionally. I like really challenging roles because I like
to push myself professionally. I find it really rewarding to be of service to others.”
Prior to joining Five Keys, Heather most recently served as Chief Policy and Advocacy Officer for EdVoice, a Sacramento-based education advocacy organization reshaping public education in California so that students from low-income communities have futures filled with opportunity. In that role, EdVoice and a coalition of supporting agencies helped achieve the passage of a landmark California early literacy law signed on October 9, 2025, that mandates evidence-based “science of reading” instruction, backed by a $200 million state budget investment for teacher training. She has also served as the Director of the Special Education Division for the California Department of Education, Executive Director of Special Education Services for the Illinois State Board of Education, and a Specialized Services Administrator for Chicago Public Schools.
From those roles she says she’s learned: “Leading large-scale systems requires fearless leadership, connection across sectors, relationships with key partners, and a willingness to pursue excellence in executing the vision and mission. It requires consistency, focus, regular time for reflection and feedback, course correction, and celebration. It requires content and technical expertise and supporting leaders and staff to bring a learner’s mindset and curiosity to their
work every day.”
Reading the Course
Before her years in state government and policy, Heather got her start in the classroom itself: as a special education teacher for Chicago Public Schools, and as an English and Special Education teacher for the Iowa City Community School District. That instinct for reading a room quickly, noticing what a student or family needed before they could name it, is something she’s carried into her first months at Five Keys.
“Deeply absorbing the institutional knowledge of the organization and its teams is my main priority, and establishing a shared operating rhythm built on trust,” she says. “There is so much to learn and lots of exciting work happening across the organization. I want to spend time observing, connecting, and learning.”
What’s struck her most is the sheer scope of the game Five Keys plays
across California.
“I have been incredibly struck by the sheer operational breadth and multi-layered impact of our ecosystem, from field operations like the LA Pit Stops to transitional employment and housing, schools, Home Free, and the E.A.T. Farm,” says Heather. “The absolute dedication of our teams to upholding the dignity of underserved populations at every single touchpoint is truly inspiring. Our work is about reducing barriers, and offering a compassionate first step toward long-term stabilization and career navigation.”
She’s also moved by “the sheer number of people the organization impacts every day, from a 75-year-old walking across the stage for a high school diploma, to residents obtaining permanent housing, and the level of investment Five Keys makes in our own employees.”
“This is the first organization that I have been part of that offers a variety of growth opportunities ranging from leadership to self-care. That’s a real investment and commitment to support our people to continue doing the great things they are doing on a daily basis.”
Five Keys leaders Heather Calomese and Dave Bates, VP of Engagement and Transitional Employment, celebrate with graduates at the Los Angeles graduation ceremony on June 18, 2026.
Holding the Wheel: It Takes a Community
Asked what from her special education and policy background she expects will carry into this role, she points to a few hard-won lessons.
“Relationships matter and relationships take time and should be built with intention,” says Heather. “No one individual can do this work alone, it takes a community effort, will, and skill to move the needle for real impact on the lives of people we serve. I have also learned to have pretty thick skin. Being in the roles in special education and policy that I have been in was not for the faint of heart. The work I’ve done and will continue to do at Five Keys requires facing challenges and finding solutions. Nothing is insurmountable. I’ve also learned that keeping the ‘main thing the main thing’ is important. The work that Five Keys does is about transforming lives and providing opportunities while keeping the work heart-centered and focused on improvements to the system. I’m also comfortable dealing with complexity and gray areas. This work is not black and white and
there is a lot of nuance to the work we do. Being laser-focused really matters.”
The Breakaway
Every so often, a rider attacks off the front alone — a long, grinding effort that only pays off if you’re willing to suffer for it. Heather has ridden that kind of breakaway before, leading advocacy behind California’s Golden State Teacher Grant alongside the literacy-equity work described above, work she describes as among the most demanding, and most meaningful, of her career.
“My belief that every human being deserves access to opportunities, resources, and support is what drives me every day. It’s a non-negotiable that we take care of each other,” she says. “That’s how real change happens.”
Scouting the Parcours
Heather grew up in St. Louis, MO and received her education at Concordia University Chicago — Educational Leadership and Administration, General; The University of Iowa — Master of Arts (M.A.), Special Education and Teaching, and The University of Iowa — Bachelor’s degree.
She launched her career as a reporter and editor in Iowa City and then at a small weekly paper in New York. While she enjoyed the newsroom, she didn’t see herself staying there long term. Education had always interested her, and she made the leap into special education through a program at the University of Iowa, a shift that’s shaped everything since. That early instinct for asking questions and reading a situation clearly still carries over into how she leads today: rigor, curiosity, and narrative alongside data.
“Data alone isn’t enough; we must use intentional narrative to illustrate systemic impact. Storytelling humanizes our work, shifting perspectives from cold compliance metrics to the lived reality of transformation and second chances.”
Special education became more than a career change. It became a community. Heather credits the students and families she’s served over the years with shaping who she is today, and says that drive to maximize independence for students and families, and to be of service to others, is exactly what she brings to this role.
“The students and families that I have served with over the years are always close to my heart and continue to drive my work.
These days her daily writing practice now centers on strategic vision, reflection, and staff communication. She firmly believes that data alone isn’t enough; we must use intentional narrative to illustrate systemic impact. Storytelling humanizes our work, shifting perspectives from cold compliance metrics to the lived reality of transformation and second chances.
Off the Bike
How do you like to unwind after a demanding week?
I’ve learned the hard way that self-care is non-negotiable for me. It varies,
but I usually can be found listening to music/vinyl, spending time with family and friends, spending time in nature, cycling throughout the Bay Area, at art museums (like the Museum of the African Diaspora), and relaxing at home. I like to keep things simple.
What’s your idea of perfect happiness?
Realizing my fullest potential as a human being. That means experiencing all that life has to offer. The ups and downs, the twists and turns, the joy, the not so joyful. Happiness to me is to experience the full spectrum of life and fulfill the highest version of myself.
Who’s a living person you admire, and why?
My mom (Heather’s dad passed away four years ago). She has been my biggest cheerleader and coach in life. She taught me the value of hard work, believing in myself, having a limitless mindset, and treating people well along the way. She was a computer programmer for the airlines in the 70s and 80s, which was rare for a woman, let alone a Black woman, at the time. She used to take me to work sometimes on the weekends and I would run around the computer room, where the mainframe computers were. She then transitioned to leading Human Resources departments later in her career and was always striving to be her best self and reach her potential. She is a fun person and a people person. She’s had some challenging roles in her career and I learned from her that even though the work is tough, bringing a sense of joy and optimism to the workplace is important. She has navigated so much in life and she continues to be a source of inspiration
to me today.
What do you consider your greatest achievement so far?
Leading high-impact advocacy and policy teams that successfully redirected state-level resources to high-need schools and underserved communities, ensuring that systemic equity is built into structural budgets rather than treated as an afterthought. My greatest achievement was drafting legislation, working with state legislators and other agencies to pass literacy legislation that will impact every elementary school student in California. It was a grueling and highly fulfilling achievement. That work has shown me that we have the capabilities to change systems that haven’t worked for decades and that we can collectively solve tough issues in California.
Who are your favorite writers?
James Baldwin. Zadie Smith. ZZ Packer. Toni Morrison, to name a few.
Describe yourself in six words.
Grounded. Dedicated/committed. Hard-working. Joyful. Positive. Creative.
What are you most grateful for right now?
I am profoundly grateful for the warm, open welcome I’ve received from the entire Five Keys family, and for the opportunity to navigate this meaningful organizational chapter alongside such dedicated colleagues.
What’s next on your bucket list?
Travel. Another century cycling ride (100-mile ride) and practicing my vinyl/DJ skills. I’d love to DJ!