Gabriella Calicchio to move from Bay Area to start at OSF in mid-November
By Holly Dillemuth, Ashland.news
A golden opportunity paired with serendipitous timing both played a role in bringing Gabriella Calicchio to the Southern Oregon stage for her newest act which, starting in mid-November, will be serving as executive director of the Oregon Shakespeare Festival.
Following a nationwide search, OSF named Calicchio to transition into the role as lead of business operations for Ashland’s world-renowned theater company that’s been held by Interim Executive Director Tyler Hokama since June 2023.
Calicchio brings with her 25 years in theater management at locations ranging from Minnesota to the Bay Area.
Although Calicchio officially begins her tenure as OSF’s fifth executive director on Nov. 12, she will start the onboarding process immediately, working closely with key leaders to get up to speed on the organization’s current operations and initiatives, according to OSF. Hokama will support Calicchio and senior staff during the transition, facilitating an effective handover of responsibilities as he steps down from his interim role.
“It’s just amazing that the timing has finally clicked and happened and here I am,” Calicchio told Ashland.news in a phone interview Tuesday. “It’s like magic – it all just came together.”
Calicchio’s first experience with OSF was in 2003 when, newly married, she and her husband spent their honeymoon in Ashland, attending five OSF plays over three days (Fun fact: Hokama also spent his honeymoon at the festival in Ashland, long before taking on the role).
The five theater performances Calicchio and her husband experienced during the short trip left an indelible impact on her, and she remembers how she felt watching world-class theater at the Allen Elizabethan Theatre.
“My husband, who was an actor, had plenty of exposure to the theater, to the festival, before that time, but I did not — I was raised on the East Coast,” Calicchio said. “I’d heard of OSF, but had never been there. We spent three days there and saw five shows and it was an incredible experience filled with artistic excellence that I had really not experienced before.
“I just remember feeling pure magic,” she added. “That feeling where you are completely transformed into this other world and other space … that’s the magic that I remember.”
Along with spending her honeymoon at OSF while serving as managing director for Marin Theatre Company, Calicchio said, she had long-term aspirations that aligned with eventually working for the Southern Oregon-based, but world-renowned, theater company.
“I had turned the organization around financially (at Marin Theatre Company) … and I already was setting my sights on something bigger and Ashland at that point was definitely in my mind, but I knew I wasn’t ready yet,” Calicchio said.
Around 2007-2008, then artistic director Bill Rauch invited Calicchio to Ashland to meet with him and others to discuss future possibilities at OSF. Rauch served in that role from 2007-2019.
“(Rauch) and I had known each other from the industry and he knew I was interested someday in that position,” she said.
They talked about what she might need to do to one day work for OSF.
“We all agreed that I needed to go run a much larger organization before I’d be ready for that experience,” Rauch said, noting that was before she took a role in Minneapolis at the Children’s Theatre Company.
Since then, Calicchio compiled an even more extensive resume, developing into what OSF calls “a seasoned leader with over 25 years of experience in the arts, who will help guide OSF as it prepares to launch its 90th Anniversary Season.”
Most recently, Calicchio served as director of Cultural Services and executive director of the Marin Cultural Association for the County of Marin in the Bay Area. She also served as chief executive officer of The Walt Disney Family Museum in San Francisco, managing director of the Tony Award-winning Children’s Theatre Company in Minneapolis; managing director of Marin Theatre Company in Mill Valley, California; and as executive director of Diablo Ballet in Walnut Creek, California.
Now, 25 years of artistic leadership experience later, Calicchio plans to retrace her steps in November to work behind the scenes for the world-renowned theater, and expressed an eagerness to take on the new challenge.
“I know things have been very challenging since the pandemic,” she said, “but … I’m heartened by how much work (Artistic Director) Tim (Bond) and Tyler have done and the staff and the board to get this festival to a more stable place, in the last year in particular.”
Calicchio said she’ll be traveling back and forth between the Bay Area and Ashland many times before she officially starts in her new role working with the entire leadership team and is looking forward to getting engaged in what’s going on during the 90th anniversary season in 2025 as well as finishing up this season.
“I recognize that OSF is unique in that it not only is an iconic hub for theater with visitors from all over the world, but that it also has really strong community roots,” Calicchio said.
“Everybody from the board to the volunteers to donors to the membership, all of those factions make up the success for an organization.”
Calicchio noted that people often ask what will you do in your first 100 days in a new role.
“I’m looking forward to meeting as many people in Ashland and surrounding communities as I can and really going on a listening tour,” Calicchio said.
“I want to go out in the community and talk with people and listen to people’s hopes and dreams for this amazing institution,” she added.
“I’d like to believe that I will be able to meet hundreds of people in an authentic and genuine way in those first 100 days and really get a feel for the local community because I know that OSF relies on the support of a much broader community, but I also believe that OSF exists because of the people who live in Ashland and the surrounding communities.”
How did she learn of the opening? That involves even more serendipity.
“Tyler (Hokama) and Tim (Bond) did a LinkedIn livestream (in June) … just to talk to people about where the organization was at and the work that they were doing and the vision for the future and I just tuned in,” Calicchio said. “I just happened to tune in and I came away from watching that just thrilled beyond belief at the work that they had done and the vision moving forward.”
After that, a recruiter who she said is also a friend reached out to her and the rest is her story.
“That just started the ball rolling again,” she said.
Her appointment follows a rigorous national search led by Arts Consulting Group (ACG) in partnership with a Search Committee of OSF board members and executive staff, according to an OSF news release.
Timing for her family played just as much of a role, too.
“My youngest, my son, was about to go off to his freshman year of college, so … my family was in a place where we could actually make a move, which I just didn’t feel we had been before,” Calicchio said.
Calicchio’s passion for the arts was ignited in her childhood, growing up in a small artist community in Vermont, according to OSF. Surrounded by visual and performing artists, she developed a deep love for theater that has shaped her career.
She earned a Bachelor of Arts in Drama and Dance from Bard College and a Master of Arts in Arts Administration and Education from Lesley University, after which she dedicated herself to leading arts organizations with a focus on growth, diversity and community engagement.
Calicchio comes to OSF with a background in nonprofit, government and corporate sectors, with expertise spanning theater, dance and cultural management, which OSF said makes her uniquely qualified to lead the organization into its next era.
“It is an immense honor to join an organization that I have long admired,” she said in a news release. “OSF’s reputation for artistic excellence is unparalleled, and I am excited to bring my diverse experiences across various arts disciplines and industries to this iconic institution,” she said in a news release. “I am particularly thrilled to return to my true passion — working in theater — and to partner with Tim Bond, the Board of Directors, the Leadership Team, and community leaders to usher in a new era for OSF. Together, we will continue to push boundaries, innovate, and inspire audiences for generations to come.”
Bond, too, expressed excitement about her appointment.
“We are absolutely thrilled to welcome Gabriella to OSF,” Bond said in a news release issued Tuesday. “Her extensive background in the arts, combined with her passion for theater and her infectious spirit, make her an ideal partner as we continue to push the boundaries of what’s possible on stage. I am eager to collaborate with her, not only to realize OSF’s artistic vision but also to strengthen our ties with the Ashland community and the broader region. We both recognize how critical this relationship is to the local economy and the cultural fabric of our area. Together, we will work to ensure that OSF remains a vital contributor to the community while expanding our impact on a global scale.”
Rudd Johnson, co-chair of the OSF Board of Directors, also expressed his excitement about Calicchio’s appointment and took a moment to recognize the significant contributions of Hokama, who has been serving as interim executive director.
“There are not enough words to describe how grateful we are for Tyler Hokama who stepped out of retirement to guide OSF through an incredibly challenging period,” Johnson said. “His dedication and leadership both to OSF and the Ashland community have been nothing short of extraordinary. Tyler’s collaboration with Tim Bond to expand our production offerings,
improve cash flow, and secure vital legislative funding for arts organizations across Oregon, including OSF, has laid a strong foundation for our future.”
Johnson, in tandem with this leadership transition, has also been elected as OSF’s sole board chair. He will succeed current chair Diane Yu, who has been serving as board chair since 2019.
“Gabriella’s visionary leadership and strategic acumen are exactly what OSF needs as we
prepare to launch our 90th Anniversary Season,” Johnson added in a news release. “Over the past year, we’ve made significant progress, but we recognize that there’s still important work ahead to stabilize and strengthen the Festival. … Gabriella’s experience and dedication to the arts will be key as we continue building on the positive momentum we’ve gained under Tim and Tyler’s leadership. We are confident that she will work hand-in-hand with Tim to carry forward OSF’s legacy of exceptional theater-making, and I look forward to working with
them both to secure a bright future for our beloved theater.”
Rauch also weighed in on her appointment to the role in a phone interview with Ashland.news.
“I’ve known Gabriella over 20 years and she is just an arts leader that I have so much respect for,” Rauch said, “and it just does my heart so much good to think of her at OSF in partnership with Tim Bond.
“I just think it’s a brilliant appointment.”
Johnson’s new term on the board of directors officially begins in January 2025. OSF said in its announcement that he plans to bring his extensive experience and dedication to the festival at a time of continued transformation.
Johnson is a longtime audience member and supporter of the festival, and has been attending OSF plays since 1996. He previously served as board chair from 2010-2012 and said he looks forward to working closely with Calicchio and Bond to help guide OSF into this next chapter, ensuring the continued success and sustainability of the organization.
Email Ashland.news reporter Holly Dillemuth at hollyd@ashland.news.
Sept. 18: Corrected spelling of Gabriella Calicchio’s name in photo captions.
