Meet The HIRE360 TEAM

AnaMaria Montes de Oca-Rojas brings nearly 20 years of experience in workforce development, nonprofit leadership, and community engagement to her role at HIRE360. As Director of Workforce Development, she leads strategic planning and manages training and career pathway programs that connect individuals to high-demand careers in the trades, clean energy, and related industries. She oversees a team of 22 staff and ensures access to union apprenticeships, wraparound services, and long-term employment.

Born in Mexico and raised in Chicago, AnaMaria was inspired by her parents, who owned two Spanish-language newspapers in Illinois. Her career includes leadership roles at Central States SER and United Way of Metro Chicago, and she is fluent in English and Spanish.

AnaMaria holds an Associate in Arts degree from Morton College, has completed multiple workforce development trainings, and is continuing her education. She has been married for 29 years and is the proud mother of two. Her community service includes board roles with Solutions for Care, Cicero Chamber of Commerce, and others.

Deborah Whitaker is a seasoned business development leader and problem solver with a deep commitment to economic equity. As Director of Business Development at HIRE360, she leads a team that provides technical assistance, access to capital, back-office support, and contracting opportunities to over 250 diverse businesses. Under her guidance, HIRE360 has helped secure well over $10 million in financing across nearly 100 business loans.

With a hands-on, individualized approach, Deborah supports minority- and woman-owned businesses in building capacity to compete on major infrastructure and development projects. Her expertise is grounded in a career that began in banking and spanned roles in international trade services, interest rate swaps, and trust divisions, as well as accounting and financial leadership at Fortune 500 companies.

Deborah holds a Bachelor of Science in Accounting and is a former real estate investor and business consultant. Her work has earned her numerous honors, including the Crain’s Notable Black Leaders Award, the Federation of Women Contractors’ Outstanding Public Service Award, the Egretha Business and Career Impact Award, and the HIRE360 Construction Advocate Award.

Jay Rowell is the Executive Director of Chicago-based HIRE360, a unique partnership between developers, general contractors, the hospitality industry, and trade unions to connect underrepresented populations to opportunities. Rowell previously served as the Deputy Treasurer for Illinois, where he oversaw the state’s $31 billion portfolio. In that role, he helped to dramatically increase the number of minority- and women-owned firms that manage the State’s investments and re-envisioned the Illinois 529 College Savings programs, earning Morningstar’s highest ratings. Before joining the Illinois State Treasurer’s office, Rowell was the Director of the Illinois Department of Employment Security, where he helped to improve the process of connecting people with available jobs, created a no-cost HR recruiting program and launched a new job board to better match job seekers’ skill sets with the needs of potential employers. Rowell earned his law degree from Loyola University Chicago School of Law and a Bachelor’s Degree in Public Communication at American University. He was recognized by Crain’s Chicago Business as a 2025 Notable Leader in Philanthropy for his work to expand economic opportunity and build more inclusive workforce systems.

Karen Larson is a seasoned finance and operations executive with more than 15 years of experience leading financial strategy in both the public and nonprofit sectors. As Director of Finance and Operations at HIRE360, she built the organization’s financial infrastructure from the ground up and now oversees a complex, multi-stream budget. In addition to fiscal strategy, Karen leads the organization’s human resources, information technology, and facilities functions, ensuring that people, systems, and space are aligned to support HIRE360’s mission and rapid growth.

Karen oversees all compliance, internal controls, and long-term planning efforts, managing a growing team of over 40 staff. Her leadership has been instrumental in the organization’s rapid growth, including the acquisition of a new headquarters and the expansion of workforce programs across the state. She is a trusted advisor to HIRE360’s executive team and board, known for integrating sound financial management with organizational development and operational excellence.

Prior to joining HIRE360, Karen served as Chief Technology Officer for the Illinois State Treasurer’s Office, where she led modernization efforts and strengthened compliance and risk management systems. 

Karen holds a Bachelor of Arts in International Political Economy from Fordham University and a Master of Business Administration with an accounting focus from DePaul University’s Kellstadt Graduate School of Business.

Rashaan Meador is a youth development leader with more than 15 years of experience designing and implementing education and workforce programs for young people in underserved communities. As Manager of Youth Engagement at HIRE360, he leads initiatives that prepare Chicago youth for success in the construction trades and related industries, guiding them from exposure to employment. 

Rashaan is a former Emmy-winning editor for TNT’s Inside the NBA, and previously served in leadership roles at Chicago Public Schools and After School Matters, where he focused on arts, workforce readiness, and mentorship. He has served on the boards of Project Osmosis and the International Voices Project and remains a dedicated mentor to emerging professionals. He holds a bachelor’s degree in Mass Communications from Shaw University. He lives on the city’s South Side with his wife, Dr. Cherie Meador, and their two children, Nasir and Nadia.

Trina Taylor is a seasoned workforce development leader with over 15 years of experience in program oversight and public service. As CEJA Program Director for HIRE360, she oversees the Climate Works Pre-Apprenticeship Program and the Energy Transition Barrier Reduction Fund Program. These initiatives, delivered through ten partners across Central and Southern Illinois, help individuals from underrepresented communities prepare for careers in the trades and clean energy sector through job readiness training, industry-recognized credentials, hands-on experience, and support services.

Prior to joining HIRE360, Trina served as Executive Deputy Director of Service Delivery for the Illinois Department of Employment Security (IDES), where she led statewide operations for Unemployment Insurance, Employment Services, Field Operations, and Fraud Prevention. She also served on the National Association of State Workforce Agencies and collaborated with the U.S. Department of Labor to advance integrity and service across programs.

Trina holds a Bachelor of Arts in Psychology from DePaul University and is known for her collaborative leadership style, commitment to equity, and deep knowledge of public workforce systems.