When Ross MacLeod arrived in Portland 14 months ago, he was already familiar with the market — but only from a distance. During his time at iHeartMedia in Miami, he’d programmed The Brew remotely. He also managed Jack in Seattle and The River in Sacramento from afar. Now, as Operations Manager for Connoisseur Media in Portland, he’s living the hyperlocal reality he once managed from 2,000 miles away. What he’s discovered is that proximity changes everything.
“I don’t think radio has the power anymore that it had 20 years ago, where we could get people to go to where we are,” MacLeod told me during our recent conversation. “We have to go to where they are.”
This simple philosophy underpins everything MacLeod is doing across Connoisseur’s three active brands in Portland. These include KINK, an iconic AAA (Adult Album Alternative) station; KUPL (The Bull), a country station; and KUFO, a newly relaunched active rock brand. While the cluster operates seven stations total, MacLoyd’s day-to-day focus on these three stations reflects strategic commitment to depth over breadth. It’s a lesson he’s learned firsthand about connecting with a market.
Finding Home in the Pearl District
MacLeod’s integration into Portland isn’t superficial. He and his wife live in the Pearl District, just steps from the downtown core. Importantly, he walks to and from the Connoisseur offices daily. This isn’t just convenient; it’s deliberate. “It was important for me to live there because I wanted to see it every day,” he explained. The couple frequent Portland’s renowned live music venues regularly. Notably, these venues number seemingly endless on any given week, from Pioneer Courthouse Square’s public events to the city’s sprawling independent concert venues.
This immersion into Portland’s culture — what MacLeod describes as “being tourists in the city we live in” — feeds directly into his programming decisions. Furthermore, it’s shaped how he approaches his team and talent. He encourages them to become genuine community participants rather than radio personalities performing behind station walls.
KINK: Protecting an Icon
KINK occupies a unique position in Portland’s radio landscape. The station is iconic within the AAA format nationally. Specifically, it represents one of the most recognizable brand names in alternative radio. MacLeod’s approach here isn’t about reinvention — it’s about preservation and optimization.
Morning show host Mitch Elliott has been at KINK for more than a decade. His connection to listeners borders on the familial. “When Mitch is away, we get so many emails asking if he’s okay,” MacLeod said. “People are genuinely worried. It’s so heartwarming and charming.” That level of listener attachment doesn’t happen by accident. It reflects years of authentic connection to a community.
The rest of KINK’s lineup includes Jared in midday. He also serves as music director and assistant program director after 14 or 15 years at the station. Gustav works afternoon drive, while Peggy Laplante hosts Sunday brunch. Additionally, she manages countless behind-the-scenes responsibilities. This is institutional knowledge made flesh. Rather than dismantling this veteran structure, MacLeod recognized what he inherited: “We didn’t have a people problem. We have some amazing people on that station who are already ingrained in this community. We just had to do some tweaking with the product itself.”
The Bull: Old Talent Meets New Energy
KUPL, branded as The Bull, presents a more complex programming picture. The station operates as “a tale of two kinds of brands,” according to MacLeod.
In afternoon drive, the station features Beat Up, a multi-award-winning national talent. He brought impressive credentials to Portland — including having raised more than $50,000 for charity just weeks before MacLeod arrived. However, the morning show tells a different story. The Stampede is a newly launched morning program featuring a fascinating mix. Jake Byron has worked at the station in previous roles. Jr. came from the top 40 format. Mallory Santick is a local talent from Vancouver, Washington, with no prior radio experience.
That last detail intrigued me. Finding radio talent outside the radio industry remains challenging. “We posted for the job and got a little bit of everything,” MacLeod explained. “You get people trying to see if it’s something they might want to move for, and then you get people who’ve been told they have a great voice while working at Home Depot.”
Mallory was different. Beyond her local roots and strong social media presence — crucial for modern radio marketing — she had what MacLeod calls “an incredibly interesting life story.” When he realized she could bring that authentic narrative to the airwaves, he knew he had something worth developing. “The three of them together have some pretty good chemistry and some magic that’s going to be a good long-term show,” he said.
KUFO: Reviving a Ghost Brand
Perhaps the most ambitious project in MacLeod’s Portland portfolio is KUFO. It’s the active rock station that disappeared from the market approximately 15 years ago. Connoisseur Media’s ownership team — Jeff Warshaw and Keith Connelly — believed strongly in reviving heritage brands with proven track records. They identified a clear programming void in the market. Specifically, the market had AAA (KINK) and classic rock formats. Both The Brew and KGON fill those niches, but no active rock station existed.
“There’s a gigantic gap between the AAA station and what’s the position of The Brew,” MacLeod observed. “We hope KUFO can just drive through the middle.” The station relaunched a few months ago. Currently, it’s running promotions while MacLeod and leadership evaluate the next phase. On-air talent represents the next conversation.
This is work in progress. It reflects Connoisseur Media’s willingness to invest in market gaps rather than simply copy what’s already working.
The Hyperlocal Mandate
Across all three brands, MacLeod and his ownership team operate from a consistent principle: be local and be present. Jeff Warshaw emphasizes street presence. Consequently, MacLeod has responded by building a robust street team. He ensures talent appears throughout Portland — not just in studios. They show up at fall fairs, concerts at the Moda Center, and smaller venues across country, rock, and AAA spaces.
“It’s being local and it’s being part of what they’re doing,” MacLeod said. “I don’t think radio has the power anymore that it had 20 years ago, where we could get people to go to where we are. We have to go to where they are.”
This isn’t radical. But it’s often unexecuted. Traditionally, radio’s default tendency has been to expect the audience to come to the station. MacLeod’s inversion — the station going to the audience — requires discipline, resources, and genuine commitment to community over mere promotion.
The People Problem vs. The Product Problem
MacLeod offered a particularly valuable insight when discussing KINK’s situation: “We didn’t have a people problem. We have some amazing people on that station who are already ingrained in this community. We just had to do some tweaking with the product itself.”
This same philosophy applies across his entire portfolio. The KXL news team belongs to this market. Similarly, the KINK on-air staff and emerging talent at The Bull are people who already belong in Portland. MacLeod’s job isn’t replacing them. Instead, he’s helping them connect their existing community roots to increasingly sophisticated radio strategy.
Building for Longevity
After 14 months, MacLeod is no longer the outsider who programmed Portland remotely from Miami. He’s become a participant in the city’s musical and cultural ecosystem. He walks its streets, supports its venues, and hires talent who live its values.
This hyperlocal approach may seem like common sense in an era when radio’s competitive advantages are shrinking. But implementation remains rare. Connoisseur Media and MacLeod are proving something important in Portland. It’s a city he describes as having “weirdness and isms that are incredibly cool.” The only way to compete is to be genuinely part of what makes the market unique. That’s not just good programming philosophy. That’s sustainability.
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David Hill serves as a Music Radio Editor, Columnist and Features writer for Barrett Media. A radio lifer with more than 30 years behind the mic, in the control room, and in the program director’s chair, David’s career spans influential stops at brands such as WIYY 98 Rock, WBAL-AM, and 99X. He has worked across multiple formats and ownership groups, including iHeartMedia and Cumulus Media, developing talent, breaking music, and navigating every major industry shift from diary to PPM and terrestrial dominance to streaming disruption. When he’s not writing or analyzing the industry, Dave runs The Tune Farm, a marketing firm built to help artists and brands grow audience the same way great radio always has—by creating connection, not just impressions. He can be reached at David@BarrettMedia.com.