The following is an article from Pacific Business News featuring Deena Dray: “Breathing new life into Diamond Head Theatre.” Mahalo to editor Kelsey Kukaua for spotlighting Diamond Head Theatre in its special section Executive Insights. Click here to read the full article.


When Deena Dray was appointed executive director of Diamond Head Theatre more than 25 years ago, she was tasked with breathing new life into a community theater that first opened in 1915.

What she initially lacked in theater training, she more than made up for with a keen business sense, having previously held positions in marketing, business development and finance at First Hawaiian Bank.

Dray was also director of the nonprofit ASK-2000 — now Aloha United Way’s
2-1-1 program — and worked as an usher at Manoa Theatre before joining Diamond Head Theatre’s board of directors in the early ‘90s.

“There was a steep learning curve coming from the board to actually working on the property,” Dray told Pacific Business News. “My predecessor took the theater in a different direction, so my job was to bring it back and earn my stripes with the community and staff. … It’s been a slow climb, but a good feeling of good work.”

Over the years, she managed to build a namesake brand – the Broadway of the Pacific – create good rapport with the community and bring on key players like artistic director John Rampage, new board members and other employees to help move the vision forward.

When Covid arrived in the Islands last March, Dray was faced with the difficult decision of whether to continue construction of the near 500-seat theater, which is being built on a lot next to the existing theater to allow shows and programs to resume simultaneously.

“Our first gift for this capital campaign was in 2013 and after an eight-year investment, we couldn’t let our sponsors down, so we figured we should do it,” she said. “We’re on target to finish by 2022. We have secured $21 million; [we] have $1.3 million to go toward the current $22.3 million cost, so we’re 95% done. Though they say the last 5% is the hardest.”

Dray said the new structure will improve production values with its upgraded technology, and include a fly loft for scene transitions, as well as better sound quality and sight lines. Other enhancements include additional restrooms, an outdoor lawn entrance and expanded spaces for the cast and class offerings.

How did Covid most significantly impact operations and finances?

Right before Covid, we were robust and in a good spot, but even with a good cushion financially, we still had to furlough most of the staff.

We thought this was going to only last a few months and sat tight from March to June [2020], before bringing people back on; we cut 25% of staff permanently. Now, we have 18 (full- and part-time) employees. That does not include contract staff such as teachers, directors, designers, and consultants, plus several hundred volunteers.

Later that year, we launched drive-ins, which were successful and well-received, as well as our Pandemic Adapted Performance series, or PAPs, which included a Christmas show, and now our sold-out summer show, “A Chorus Line.” Everybody has masks when they come here, we aren’t selling concessions, and continue to enforce City guidelines [on permitted gatherings].

How is the theater funded?

Ticket sales don’t support the entire operation – if that were the case, we’d have to charge a lot more. Instead, we have a subsidized operation, run primarily on individual-based donations. It comes out to about 40% contributed income, like donations, and 60% earned income.

Because I’m a banker by trade, I’ve been committed to setting money aside. You need to project from success, not from crisis to crisis, or when you’re on the precipice of disaster. You must know your market, and ours is 80% local residents.

What are your priorities now?

Right now, my goal is to get subscribers back up to where we were in 2020, with 2,920 current subscribers. We’ve started strategic planning with talks about budget and size for our upcoming season in September.

Education remains important to us, especially those who are involved in the arts at an early age, they tend to develop a confidence that stays with them their whole adult life.

Live theater is what we do and it’s our core mission here. We want everyone back in their old seats and able to enjoy the show together. I read in The New York Times about a phenomenon called “Collective Effervescence” – something special about a group coming together around a shared purpose, in which we’ve been missing out on for this last year and a half.

When sharing that mutual experience, i.e. watching a good show and laughing, crying, or applauding together, it makes our audiences happy beyond just the building walls, carried out into the community.