The Wailea Community Association, a nonprofit corporation that stewards Maui’s 1,500-acre master-planned Wailea Resort community, recently named its next leader.
As general manager, Matt Chierek will oversee operations, finances and strategic planning, per the association. He succeeds Bud Pikrone, who announced his retirement in May after 25 years in the role. Pikrone’s last day was Sept. 30.
“It’s an honor and privilege to serve this community and to help carry forward the legacy that so many people have built over the years,” Chierek said in emailed responses to Aloha State Daily. “Wailea is more than a destination – it’s a community built on care, connection and pride. My goal is to honor that foundation while preparing for a vibrant, sustainable future.”
As part of those preparations, he said his immediate focus is on strengthening the association’s internal operations such as improving financial transparency, modernizing systems and updating processes to better support its members and partners.
“We’re also reorganizing our Design Committee and will be re-engaging with community stakeholders to ensure that Wailea continues to reflect the highest standards of design, landscaping and environmental care,” Chierek added.
More long-term goals include “maintaining the beauty and integrity of Wailea while balancing modernization, sustainability, and fiscal responsibility,” he said.
With that in mind, he plans to update the organization’s multi-year strategic plan “to help guide priorities, strengthen operations, and align our initiatives with the community’s long-term vision.”
“I’m especially excited to form new partnerships that foster collaboration between the various entities within the resort, local organizations and nonprofits – strengthening community engagement, cultural connection, and shared stewardship throughout Wailea,” according to Chierek.
He continued, “What drew me to the Wailea Community Association was the opportunity to serve the broader Wailea community – to help steward not just one property within it, but the entire resort area that makes Wailea so special. It’s a chance to combine my operational and financial background with a genuine passion for community-building and collaboration.”
Chierek started his career in community and resort management more than 20 years ago, he said, “working my way up through housekeeping, operations, facilities, and various management roles all of which provided me a deep understanding of how well-run communities function – not just physically, but financially and culturally.”
“Most recently, I spent over a decade as the general manager at Wailea Point Village, where I gained firsthand experience in managing complex budgets, sizeable teams, large capital projects and the elevated standards that come with a luxury property.”
Volunteerism is also important to Chierek, who supports local events and nonprofit initiatives, especially those addressing environmental stewardship, ocean and land conservation and community safety.
When asked about plans to continue the association’s charitable giving arm, he responded, “Yes, we absolutely plan to continue the association’s charitable giving and community support. Wailea has a long tradition of giving back, and we want to ensure that tradition grows even stronger in the years ahead.”
For Chierek, leading with transparency, consistency and approachability is vital.
“My goal is to empower the people around me – whether it’s our staff, board members, or community partners – by giving them the tools and clarity they need to succeed,” he said. “I’ve been reminded that leadership is about listening as much as it is about directing. Every property and individual bring a unique perspective, and the best decisions often come from collaboration and shared insight.”
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Kelsey Kukaua Medeiros can be reached at kelsey@alohastatedaily.com.
