Jessie A Greenwald
Waukesha
Summary
Results-driven communications and program leader skilled in managing substantial grants and diverse employer partnerships. Specializes in public initiatives, recruitment, stakeholder engagement, and team leadership across higher education, workforce, nonprofit, and public sectors. Aligns strategies with institutional goals to enhance engagement and drive successful event execution.
Overview
22
22
years of professional experience
Work History
Program Specialist
Employ Milwaukee, Inc.
Milwaukee
01.2022 - Current
- Attained an 87% placement rate for program graduates into apprenticeships within six months, demonstrating program effectiveness and measurable workforce impact.
- Establish and sustain an employer pipeline of 150+ regional partners supporting Registered Apprenticeship expansion.
- Coordinated with Department of Workforce Development, employers, and technical colleges to launch certified pre-apprenticeship programs aligned with skill requirements and pathways into Registered Apprenticeship and employment.
- Partnered with City of Milwaukee Water Works to recruit and prepare participants for civil service career pathways, aligning training with public-sector hiring standards to enhance career readiness.
- Supervise and support program staff while coordinating cross-departmental teams to deliver recruitment, communications, and participant services.
- Compile and submit quarterly federal reports, maintaining audit-ready documentation and comprehensive grant files.
- Coordinate with fiscal teams to prepare budget justifications and monitor allowable expenditures.
- Participate in grant monitoring reviews, ensuring policies, procedures, and communications meet statutory and regulatory standards.
- Developed messaging and materials for students, employers, funders, and community partners to increase program awareness and engagement.
Vice President, Board of Directors
Wisconsin Area Music Industry (WAMI)
01.2022 - Current
- Serve on the executive leadership team of a statewide nonprofit supporting musicians and creative-industry professionals.
- Led strategic initiatives for communications, marketing, media relations, and stakeholder engagement to enhance organizational impact.
- Directed a successful turnaround of the organization’s annual awards show through targeted marketing strategies and enhanced attendee experience. This resulted in doubled attendance and the acquisition of three new corporate sponsors, significantly increasing financial sustainability and organizational visibility.
- Oversaw branding, messaging, and promotions across online platforms and live events, ensuring alignment with mission and maximizing outreach.
- Collaborate with board members, staff, contractors, and volunteers to ensure communications correspond to organizational mission and goals.
- Represented organization with partners, sponsors, and media, strengthening external relationships and elevating organizational profile.
- Statewide Nonprofit
Board Member; Board Chair (Four Years)
Wisconsin FACETS (WiFACETS)
01.2014 - Current
- Chaired board for four years, governing strategically, facilitating productive meetings, and partnering with executive leadership to implement priorities supporting students and families across Wisconsin.
- Led long-term board initiatives for statewide organization enhancing academic access, equity, and student success.
- Statewide Nonprofit
Senior Program Coordinator
Waukesha Workforce Development
Waukesha
01.2016 - 12.2021
- Oversaw more than $4 million in federal and state grants, ensuring strategic alignment and statutory compliance. Achieved a 98% compliance score.
- Executed outreach and recruitment plans with post-secondary institutions, increasing student enrollment in grant-funded training programs.
- Coordinated academic support and follow-up communications, guiding participants from enrollment to graduation and enhancing completion and placement outcomes.
- Collaborated with colleges and employers to design training programs that meet identified workforce needs.
Program Director
ANS Home Health Services
Milwaukee
01.2014 - 12.2016
- Led strategic planning and program development initiatives, aligning goals with community needs and resources.
- Created and launched state-certified Corporate Guardianship Program, facilitating comprehensive business planning and operational implementation.
- Managed interdisciplinary teams including registered nurses and case managers.
- Collaborated with courts, county agencies, and legal partners to expand referral pipelines and service delivery.
- Directed care management and coordinated case services for over 750 members, enhancing service delivery under Milwaukee County contracts.
Support Services Director
Easter Seals Southeast WI
Milwaukee
01.2004 - 12.2013
- Directed multi-program service lines to enhance support for individuals with disabilities across Southeast Wisconsin.
- Managed program budgets exceeding $1.5 million and supervised multidisciplinary teams.
- Led program transitions related to Medicaid expansion and county waiver systems.
- Implemented data-driven management practices to improve process efficiency, ensure compliance, and enhance sustainability.
Education
Master of Public Administration (MPA) - Personnel Management
Upper Iowa University
Bachelor of Science - Human Services, Psychology Minor
Upper Iowa University
Associate Degree - Human Services, Psychology Minor
Milwaukee Area Technical College
Skills
- Program development
- Grant writing
- Stakeholder engagement
- Budget management
- Data analysis
- Compliance auditing
- Labor market analysis
Timeline
Program Specialist
Employ Milwaukee, Inc.
01.2022 - Current
Vice President, Board of Directors
Wisconsin Area Music Industry (WAMI)
01.2022 - Current
Senior Program Coordinator
Waukesha Workforce Development
01.2016 - 12.2021
Board Member; Board Chair (Four Years)
Wisconsin FACETS (WiFACETS)
01.2014 - Current
Program Director
ANS Home Health Services
01.2014 - 12.2016
Support Services Director
Easter Seals Southeast WI
01.2004 - 12.2013
Master of Public Administration (MPA) - Personnel Management
Upper Iowa University
Bachelor of Science - Human Services, Psychology Minor
Upper Iowa University
Associate Degree - Human Services, Psychology Minor
Milwaukee Area Technical College