The Street Trust picks former TriMet planner and Charlie Hales staffer as new executive director

Jillian Detweiler.
(Photo: The Street Trust)

Jillian Detweiler is the new leader of The Street Trust.

The 51-year-old northeast Portland resident who lives on the Going Street Neighborhood Greenway and tells us she “cheered” when its sharrows appeared in front of her house, is a new kind of leader for an organization in the midst of transformation.

Detweiler is currently the interim development manager for Prosper Portland (formerly the Portland Development Commission). Before that she served three years as a policy director for former Mayor Charlie Hales — her second stint on Hales’ team after working with him out of college in the mid 1990s.

After earning a Masters degree in city and regional planning from the University of North Carolina in 1992, Detweiler worked on planning and permit issues for then Commissioner Hales from 1995 to 2002. After that she spent 12 years at TriMet — first as a planner and then as director of real estate. In that position she oversaw $240 million in property acquisitions as part of the MAX Orange Line project.

With her background of city hall politics, transit planning, and high-profile development work, the selection of Detweiler reflects The Street Trust’s goal of becoming a political powerhouse with an expansive portfolio and the funding streams to make it all possible. She has no experience in professional bicycle activism, and that’s likely part of the reason she was hired (we heard from sources that The Street Trust favored candidates with more political experience).

Detweiler’s past experience via Linkedin.

In a statement released this morning The Street Trust Board Chair Justin Yuen said he expects Detweiler to, “Continue the transformation of The Street Trust into an organization that recognizes that the benefits of active transportation need to be shared equitably and serve people displaced from neighborhoods across the region.”

Here’s more from Yuen:

“The choices our region’s leaders and citizens make over the next few years will determine what kind of transportation system we use for the next several decade. State and regional agencies are considering billions of dollars of investment in transportation infrastructure right now — we want that infrastructure to make a major difference on streets in neighborhoods across the region… The Board and staff of The Street Trust remain deeply committed to the long-term vision of building a place that embraces biking, walking and transit not just for some, but for all those that call our region home.”

Detweiler takes over an organization with 15 paid staff and an annual budget of $1.3 million. With a recent change to their name and mission, and major staff turnover in the past few years, The Street Trust is desparately in need of stable leadership. Gerik Kransky, The Street Trust’s policy director, recently told us that his efforts to balance the interests of cycling and secure funding in the statewide transportation package is the “toughest political challenge” he has faced in his seven-year tenure.


I chatted with Detweiler on the phone yesterday. The Q & A below has been edited for clarity:

What part of town do you live in?

“I live on the Going Street bikeway around 41st and Alberta Court. I cheered when the sharrows appeared in front of my house! The bikeway is my regular route and I just love it. I remember when there were stop signs every other block and it was hard to make progress. It felt safer to ride at night because at least you could see headlights coming toward you. I just love it now! For me, personally, it’s one of the best accomplishments made during the Sam Adams administration.”

What’s your relationship to cycling?

“I have two bikes… I’m a multimodaler and usually I take transit. I worked for TriMet and felt I ought to be using the service I was working to provide. My route was the 75 bus to Hollywood transit center than I’d switch to the MAX.

I’m a little more of a fair weather bike rider. I ride my bike a lot for errands, seeing friends… But I’ve had jobs that require nice clothes and I can’t always manage the changing of the [cycling] costume in harsh weather. My husband rides in any weather. He’s a mountain climber; but I say the most dangerous thing my husband does is ride to work and it shouldn’t be that way.”

Why did you apply for The Street Trust job?

“I’m maybe not the only person who, post-Trump election, wants to double-down on efforts to make our society a better place. And for me, transportation has always been a passion. I view The Street Trust’s evolution as a move to become inclusive and to address the equity gaps we see in the city and that is very important work to me. I love the size of the organization. It’s had staying power [founded in 1990]. And I’m at a point in my career where I felt I wanted to step up and lead an organiztion. I felt incredibly lucky that just as I was reaching that point, this position was open.”

Would you have applied if they were still the Bicycle Transportation Alliance?

“Maybe not… I might have applied, but would not have gotten the job.

I think my experience speaks to the broader agenda. I’m not just transit-focused; but the way I’ve been able to bring it together with affordable housing, inclusive public processes and that broader agenda, also speaks to where I have some depth of relationships in the community that has ties to funding that could support the The Street Trust.”

What part of their mission is most exciting to you?

“I’m not quite there yet in terms of understanding everything they do. As ED [executive director], there are some wonderful people at the organization and the thing I’m most excited about is making sure they are supported with the resources they need and there is stable funding. I love the encouragement work they do. Learning about the Safe Routes to School Work and encountering classes where The Street Trust gets kids onto bikes for the first time — that makes me weepy!”

Is there a part of the transportation debate advocates are missing? And can you bring it to the table?

“While I was in [Mayor] Hales’ office we felt there was a kind of void for how much community organizations were present in city hall. I think there’s room to get more attention on bike transportation and other transportation needs.

I mean, sadly, we’ve had some difficult politics in the city post-Trump election, and those have taken up a lot of oxygen. Housing has taken up a lot of oxygen; but transportation is the second largest housing cost for most households and I think we can help policymakers and people that make decisions about public investments understand that making it possible for people walk and bike and take transit can have real economic benefits for them.”

What do you think is the biggest transportation issue facing the Portland region today?

“I put safety first. I don’t know if the Vision Zero moniker has caught on enough; but it feels like every morning… there’s… wasn’t there just another pedestrian fatality at 122nd and Division? So yes, safety.

I also hear a hunger — especially among my cyclist friends — for, what’s it going to take to get us to the next level? I would love to see more mobilization around separated bikeways. I don’t claim to know all the details of the feasibility of them; but a Sullivan’s Gulch bikeway sounds terrific because of how it could link in the Gateway area.”

There’s a debate in the community about The Street Trust’s shift toward a more conservative activism style in recent years. Where do you fall on the spectrum of advocacy style from grassroots rallies and marches on street corners, to behind-the-scenes relationship building and political lobbying?

“I believe short-term wins are really important to keeping people motivated and keeping spirits high of those who support us doing good work. It’s much harder to do that on the long-term policy and funding projects. I would hope to get the resources and staffing necessary to define some discreet, short-term improvements to make happen and then celebrate those victories.”

For many people, The Street Trust is still “the bike group”. How do you respond to people concerned that you don’t have any experience in bike advocacy?

“I think the bike culture is a really distinguishing feature of Portland and would like to see it extended to the region. I had the opportunity to travel with Mayor Hales, the mayor of Austin [Texas] and former US DOT Secretary Anthony Foxx to look at cycling culture in three Scandinavian cities… Cycling is a real passion of mine. Cycling may not be for everyone; but we’ve got to expand the number of people who feel safe to meet all their transportation needs. It’s the healthiest and cheapest ways to get around. I in no way want to diminish the importance of cycling.”

Anything else you want to share?

“I’m really excited! The work couldn’t be more important to me. When I saw the job posted, literally my heart just soared! And i’m really looking forward to all of the people I expect to meet and enlisting their support to achieve our goals.”

Detweiler is the first woman to lead The Street Trust since 2005. Her first day on the job is August 7th.

— Jonathan Maus: (503) 706-8804, @jonathan_maus on Twitter and

BikePortland is supported by the community (that means you!). Please become a subscriber or make a donation today.