Recently, PPA and CityWise announced a strategic partnership. As explained in the press release, “the two firms will collaborate on targeted projects by leveraging their respective strengths and capabilities. Both PPA and CityWise aid a diverse array of clients, including state and federal government agencies, nonprofit organizations, and philanthropic foundations.” Our teams have already worked together on projects taking on homelessness in Pasadena (California), Boulder County (Colorado) and Lansing (Michigan). In this interview, you will get a chance to meet the team behind CityWise, Anna Jacobsen and Diana Trejo.
What drew you to evaluation?
For both of us, evaluation has always been more than just a tool. It has been a consistent thread throughout our careers and a method to translate good intentions into better outcomes. Anna first experienced its impact at a children’s hospital, where data improved care in real time, and later found herself building evaluation tools in nonprofit roles, which led her to focus on evaluation during graduate school and in public sector work. Diana entered evaluation through her work in public health, community engagement, and local government, where she saw how policy, funding, and lived experience intersect. Evaluation became a way to bridge the gaps in these areas and use critical thinking to drive meaningful change. Over time, we both began to see evaluation as central to how systems learn, grow, and better serve the people they are meant to support.
How did you meet?
We met while working at the City of Pasadena’s Housing Department, where we had the opportunity to collaborate on the City’s annual grant application for homeless service funding, followed by the homeless count. These projects marked the beginning of our partnership and our friendship. We quickly discovered how naturally and effectively we collaborate. Our skills complement one another and we bring different perspectives and strengths to the table. What we had in common was just as important: a shared passion for systems change, a drive to center community voices, and a deep commitment to equity.
Over time, what began as a working relationship naturally evolved into a meaningful partnership. We realized we were both drawn to work that pushes beyond surface-level solutions to address root causes. We also learned we had quite a bit in common: we’re both alumni of the same undergraduate and graduate schools, and we share a genuine passion for creative problem-solving, strategic thinking, and showing up for our communities with curiosity and care.
How did CityWise begin?
CityWise began with a conversation, one of many between two working moms navigating the challenge of pursuing meaningful and impactful work while being present for our families. As systems thinkers at our core, we envisioned a consulting firm where we could channel our creativity, expertise, and values into projects that truly matter while also having the flexibility to thrive professionally and personally. We wanted to build a firm that prioritizes collaboration and community, with the freedom to focus on projects that align with our values and the kind of change we hope to support.
What kind of projects inspire you?
We’re most inspired by projects that allow us to work directly with communities, especially at the local level. We’re particularly drawn to cities and grassroots organizations because they are often closest to the challenges and most nimble in driving responsive, impactful solutions. Whether we’re facilitating community engagement, developing policy recommendations, or evaluating program outcomes, we find meaning in work that amplifies local voices and strengthens capacity for long-term change.
What would you say are CityWise’s core values?
At CityWise, our values show up in how we work, not just what we say. We care deeply about equity, not just as a buzzword, but as a commitment to listening, noticing who is missing from the table, and designing systems that serve people better. We value relationships and the trust they are built on. That means showing up with humility, being clear about what we know and what we are still learning, and always centering the voices of the people most impacted.
We also believe that care is part of the work. Care for our clients, our collaborators, and the communities behind every dataset or policy memo. Our values are what guide us when things are complicated, and they help us hold onto what matters most.
What policy areas do you focus on?
Our work has always been rooted in housing and homelessness, where we’ve spent years supporting efforts to better serve people who are often overlooked by public systems. Over time, our focus has expanded to include public health, community development, parks and recreation, and cross-sector work that connects these areas. We’re always exploring new opportunities that align with our mission to support resilient and equitable communities.
At the core of our work is a belief that systems should work for everyone. We’re drawn to projects that help communities think bigger, work smarter, and co-create solutions that are built to last.
How did the strategic partnership with PPA come about?
PPA has been part of our story from the beginning. They were our partners on one of the very first project we took on under the CityWise name, Pasadena’s Homelessness Plan. From the start, we appreciated their thoughtfulness, deep expertise, and collaborative spirit.
This year, we had the chance to work together again on the City of Lansing’s Comprehensive Study on Homelessness, and it reaffirmed how naturally our teams work together. Our partnership with PPA is a step toward formalizing that connection. It allows us to continue building the kind of firm we envisioned: one that supports meaningful work and full lives, while expanding our ability to take on larger and more complex projects. With PPA’s support and experience, we are able to grow while staying true to what matters most to us.
Thank you for speaking with us today!