Outlier Media announces leadership transition

I’m writing to share some news with the Outlier Community. After five transformative years — for me and for Outlier — I will be stepping down as executive director and assuming a position on the Outlier Media board of directors later this summer. I share this news with gratitude, optimism and excitement about the future of Outlier and the leader succeeding me.

What an incredible journey working to build Outlier has been. Together, we’ve grown from a model to a news organization, dedicated to providing Detroiters with vital information they need to navigate their lives. From housing to transportation, from public meetings to economic opportunities, we’ve strived to be a beacon of accountability and transparency.

We have secured more than $7 million in philanthropic support since our launch in late 2016. Thousands of readers and supporters like you, from residents to business owners, have financially invested in creating our newsroom. We grew from a startup budget of $75,000 when I joined in 2019 to a $1.8 million operating budget in 2023. Along the way, we expanded our reach and forged partnerships that strengthened our impact — a testament to the passion of and for this organization.

I am immensely proud of what we’ve accomplished during my time at Outlier. We have achieved more than Sarah Alvarez and I dared to dream in those early days of our partnership. And while we may not have envisioned what Outlier would become, we always knew it was bigger than us. We built this organization to serve its purpose in perpetuity, providing a pipeline for new leadership.

As we worked on our strategic plan in the summer of 2023, I wanted the team to start imagining an Outlier that existed past my tenure. We worked together to think of what the next co-leader, working alongside Sarah, might bring to the table to push our mission and team further into an equitable and just future for Detroiters. It was critical for us to find someone who would ensure that our work is represented well by a leader who loves Detroiters and who also uniquely understands the challenges and opportunities of the journalism business and our city.

We’ve found that leader in Orlando Bailey , who will join our team on June 3 as executive director. We’ve long admired Orlando’s work and deep commitment to Detroit. He is an Emmy Award-winning journalist and currently serves as the director of engagement for BridgeDetroit and co-host of the podcast Authentically Detroit . Previously, he served as chief development officer for the Eastside Community Network.

Equally as important, Orlando is a lifelong Detroiter who loves this city and is beloved by its residents. His background in journalism, community engagement, nonprofit development and entrepreneurship makes him uniquely qualified to lead Outlier at this pivotal time. Orlando will lead fundraising efforts, sustainability and organizational direction.

To help ensure a smooth transition, Orlando and I will work in tandem for two months. My last day as a staff member will be Aug. 9.

While my role and relationship with Outlier are changing, the essence of what we’ve built together is enduring. Outlier Media Founder and Editor-in-Chief Sarah Alvarez will continue to head up journalistic coverage and oversee news products. She and Orlando will work as co-leaders, as she and I have over the last five years. Our team will continue to work daily with our neighbors to inform and serve Detroiters. We’ll also continue to spread our service and participatory journalism practices across Detroit, the country and beyond.

This transition is the realization of my greatest hope for Outlier — that we would build an organization strong enough to attract excellent leaders to steward it long after my time here. Mission accomplished.

To the Outlier team, I want to express my deepest gratitude to each of you, team members past and present. Your unwavering commitment to our mission has been the driving force behind our success. You trusted my leadership and have made me better in every possible way. I know you will continue to lead with integrity and innovation in the years ahead.

To our supporters, partners and the communities we serve, thank you for believing in Outlier Media and the power of accessible, actionable information. Your trust and collaboration have been instrumental in our journey, and I am profoundly grateful for your ongoing support.

There would be no Outlier without the relentless genius of Sarah, my business partner, but most importantly my friend. You trusted me to co-lead this work with you and gave me the greatest opportunity, anchoring my love for Detroiters in work that transforms people’s lived experience in this city. Together, we climbed a mountain and not once did I feel alone on that climb. Thank you.

While I may be stepping down from my role as executive director, my commitment to the mission and values of Outlier Media remains unwavering. My plan is to continue doing work that centers communities, addresses harm and uses the art of storytelling to deepen connection. I look forward to cheering on this organization’s continued growth and impact, and I am excited to see what the future holds for Outlier and Detroit.

My work at Outlier is my love letter to the city that raised me, Detroit.

It’s a thank you to the people who taught me to love myself and my neighbors, Detroiters.

This place, my hometown, has shown me time and again the boundless possibilities of hard work matched with abundant faith.

It has been an honor and a joy to be part of this remarkable journey.

Outlier Media announces leadership transition · Outlier Media