City Awake’s Ten Outstanding Young Leaders

Each year, we honor ten of the region’s emerging young leaders from the public, private, and nonprofit sectors who have demonstrated a commitment to improving the civic and business environment and the quality of life in Greater Boston. These emerging leaders must have held a leadership position within their organization or community, must live or work in Greater Boston for 1+ years, and must be an inclusive leader who supports and encourages an equitable and diverse culture.

The Ten Outstanding Young Leaders Awards recognize the accomplishments of young professionals who have made the Greater Boston region the best place for all businesses and all people to thrive. We are explicitly awarding individuals who address barriers and support equity. They are leaders whose principles embody what it means to create a diverse, inclusive, and equitable environment, culture, organization, or community.


City Awake centers young professionals, seeking to welcome and retain them in Greater Boston with an intentional strategy of cross-sector collaboration to increase their social capital through a blend of programming. Its programming is designed to promote civic engagement; connect them to personal and professional networks across industries and communities; and strengthen the region’s inclusivity efforts while highlighting its cultural vibrancy.

Interested in learning when the 2024 TOYL nominations will open? Sign up for our newsletter!

Questions? Reach Out

Jessica Sanon
Jessica Sanon

Senior Program Manager

Greater Boston Chamber of Commerce

Congratulations to our 2023 TOYL Honorees!

Alain Mathieu

Attorney, Mintz

Alain is the son of Haitian immigrants who grew up on Long Island, NY. He has been in New England for 15 years, during which he studied at Bowdoin College, attended…Read more

Anthony Richards

Vice President of Equitable Business Development, MassHousing

Tony Richards is the Vice President of Equitable Business Development at Massachusetts Housing Finance Agency (MassHousing). In his role, he works intentionally…Read more

Brian Awe

President, The Fallon Company

Brian Awe was named president and partner of The Fallon Company in March 2022. He is responsible for all business operations and plays a pivotal role in creating,…Read more

Carl Rodrigues

Chief Executive Officer, Harvard University – Harvard Allston Land Company

Carl serves as the Chief Executive Officer for Harvard Allston Land Company (HALC) where he is responsible for the development of Harvard University’s 36-acre…Read more

Chareeda Rustanavibul

Vice President, Startup Banking | Chief Convention Director, Silicon Valley Bank | NAAAP Boston

Chareeda Rustanavibul is a startup enthusiast, community builder, DEI advocate, and nonprofit executive. Chareeda works at Silicon Valley Bank as a Vice President…Read more

Gary Prado

Senior Legal Counsel, Fidelity Investments

Gary Prado is Senior Legal Counsel at Fidelity Investments, where he serves as chief counsel to Fidelity’s private equity business, Devonshire Investors. Prior…Read more

Guadalupe Hayes-Mota

CEO & Founder, Healr Solutions

Guadalupe Hayes-Mota is a biotechnologist, entrepreneur, professor, and public servant with a diverse background spanning the private, public, and nonprofit sectors…Read more

Jessica Carless

Staff User Experience Researcher, Google

Jessica Carless is a User Experience Researcher on the Android team at Google Inc, where she leads innovative GenAI teams and workspaces to shape the future of mobile…Read more

Kleida Martiro

Partner, Glasswing Ventures

Kleida Martiro is a Partner at Glasswing Ventures with specialized expertise in data science, entrepreneurship, and product management. As the former Head of Data…Read more

Qingjian “QJ” Shi

Director, Asian Business Empowerment Council, The Boston Foundation

Qingjian Shi is a highly accomplished leader and advocate for the Asian American business community. Currently serving as the Director of the Asian Business Empowerment…Read more

The TOYL Honorees have demonstrated at least one of the following qualities:

Nominee Criteria

  • The nominee has held a leadership position within their organization or community.

  • The nominee is under 40 years old.

  • The nominee must be an inclusive leader who supports and encourages an equitable and diverse culture.

  • The nominee must live or work in Greater Boston for 1+ years .

  • Thank you to our supporters!