Downtown Bend Business Association Leader Resigns

Rachel O’Rourke, the leader of a prominent downtown Bend business group, announced plans this month to step away from her role amid a period of major upheaval for the organization.

Days before the resignation went public, the Downtown Bend Business Association also announced it would redo the process for a recent board of directors election.

The turmoil comes after discussions over the prospect of paid parking were met with fierce pushback from property owners and the public.

“Obviously, there’s been a bit of a stirring of the hornet’s nest around the parking thing,” said Teague Hatfield, owner of the Bend Shoe Co. and interim president of the association’s board.

Three board members have also resigned separately within the past month, citing health, personal and business reasons, according to Hatfield.

O’Rourke told the board June 30 of her plans to resign, although she plans to stay on for three months to help with the transition. O’Rourke took over as executive director of the business association in April 2024 after years working in business strategy and marketing.

“My decision was a personal and professional one,” O’Rourke said in an email to the Source. “After two years in this role, I feel it’s the right time to pursue new opportunities and challenges. I’m proud of what we’ve accomplished during my time at the DBBA, and I’m committed to leaving the organization in a strong position.”

The downtown business group has seen relative instability in its top role in recent years. The previous director, Shannon Monihan, resigned after two years and sued the organization for $1.8 million, alleging sex discrimination, harassment, retaliation and negligent hiring.

The salary for the director role is paid with self-imposed fees that downtown Bend property owners pay through an Economic Improvement District assessed by the City of Bend. About $331,000 will be generated by the district this year, according to Cyrus Mooney, business advocate with the City of Bend. Besides salary for staff, the revenue pays for things including beautification, like lighting and flower baskets, and marketing for downtown.

The downtown director position is also at the center of a business association wrapped up in City politics. Last year, the downtown association lobbied against the prospect of turning some downtown streets into pedestrian plazas. O’Rourke went to the Bend City Council with a survey showing more than half of business owners opposed using parking spaces for restaurant seating. Most recently, O’Rourke and the downtown association drafted a plan for a new parking system that included taking away free street spaces for most of downtown.

City elected leaders quickly supported the idea, but some property owners launched an opposing petition that gathered more than 1,500 signatures.

Hatfield said the downtown association is still gathering feedback on the draft parking plan.

Part of the work ahead will be creating a unified vision not only for downtown, but also for what the role of the executive director should be, Hatfield said.

“How much of this is beautification, how much is marketing and events, how much of this is a bit of a voice for downtown Bend, how much of this is a liaison with the City?” Hatfield said.

He added, “I think there’s some lack of clarity among the stakeholders.”

The downtown association will hold new board elections this month to replace the elections held earlier this year. The association’s board said in a July 2 newsletter that “questions were raised regarding the election process” and a new election was the best path forward “to ensure all stakeholders have confidence in the outcome.”