Director of Workforce Policy and Strategy
Department:
Policy, Compliance, and WIOA Programs
Reports To:
President and CEO
Pay Range:
Supervises:
Compliance Manager, WIOA Program Manager
FLSA Classification:
Exempt
Approved By:
Chief Executive Officer
Revision Date:
9/3/26
JOB PURPOSE:
The Director of Workforce Policy and Strategy provides strategic leadership for Employ Milwaukee's workforce development policy, WIOA Title I-B programs, compliance, contracting, performance management, and workforce system strategy. The position ensures policies, programs, contracts, and accountability systems are aligned to produce meaningful outcomes for job seekers, employers, and the broader workforce system.
The Director serves as Employ Milwaukee's lead subject matter expert on workforce development policy and strategy, monitoring legislative, regulatory, funding, labor market, and workforce trends and translating them into actionable organizational priorities and recommendations.
The position provides leadership to the WIOA Program Manager and Compliance Manager and works collaboratively across departments to improve service delivery, strengthen employer engagement, maximize workforce investments, enhance organizational performance, and advance Employ Milwaukee's strategic goals.
ESSENTIAL DUTIES and RESPONSIBILITIES:
Workforce Policy Leadership & Advocacy
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Serve as Employ Milwaukee's lead resource on workforce development policy, funding, regulations, legislation, and emerging workforce issues.
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Monitor and analyze policy developments and provide strategic recommendations to executive leadership, the Board, and workforce stakeholders.
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Develop policy positions, briefing materials, presentations, and recommendations that advance Employ Milwaukee's mission and strategic priorities.
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Represent Employ Milwaukee with policymakers, workforce boards, government agencies, employers, educational institutions, and community partners at the local, state, regional, and national levels.
WIOA Strategy, Program Operations & Performance
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Provide strategic oversight of WIOA Adult, Dislocated Worker, and Youth programs and supervise the WIOA Program Manager.
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Establish service delivery strategies that improve participant engagement, training completion, employment outcomes, and employer satisfaction.
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Ensure WIOA programs, providers, and contracted services operate as an integrated workforce system aligned with organizational goals and labor market demand.
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Monitor provider performance and direct continuous improvement efforts related to quality, compliance, participant outcomes, and operational effectiveness.
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Identify and address barriers, gaps, inefficiencies, and opportunities to improve workforce program performance and customer experience.
Training and Employer Talent Strategies
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Lead Employ Milwaukee's strategic approach to employer-funded and publicly supported talent development.
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Develop and implement a comprehensive Incumbent Worker Training strategy that enables employers to upskill existing employees, respond to changing technology and skill requirements, retain workers, improve productivity, and create opportunities for career advancement.
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Collaborate with the CEO and Business Solutions Manager to increase employer awareness and utilization of public workforce funding for incumbent worker training and other talent development strategies.
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Lead the development and continuous improvement of Employ Milwaukee's On-the-Job Training strategy.
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Establish OJT policies, processes, employer eligibility criteria, reimbursement strategies, performance expectations, and outcome measures in collaboration with the CEO and Business Solutions Manager.
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Identify opportunities to use OJT strategically to help employers hire individuals who need additional skills while providing participants with meaningful pathways into employment.
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Lead development of customized training strategies that respond to documented employer and industry skill needs.
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Work with the CEO and Business Solutions Manager to identify employers and industries where IWT, OJT, customized training, apprenticeships, or other work-based learning strategies can address talent shortages.
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Develop strategies for braiding WIOA and non-WIOA funding to expand employer access to training resources.
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Work with CEO and Business Solutions Manager to establish measures to assess employer utilization, participant outcomes, employer satisfaction, return on investment, and business impact associated with training strategies.
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Position Employ Milwaukee as a strategic talent partner that helps employers both hire talent and develop the talent they already have.
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Lead Employ Milwaukee's overall strategy for WIOA-funded training investments.
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Lead the development, implementation, and continuous improvement of Employ Milwaukee's Individual Training Policy and related training procedures.
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Establish strategies to increase the number of participants who enter, persist in, complete, and benefit from high-quality training aligned with employer demand.
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Ensure training investments are targeted toward occupations and industries that provide meaningful employment and advancement opportunities.
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Develop strategies to improve training completion by identifying and addressing barriers related to supportive services, transportation, childcare, financial instability, academic needs, technology, and other factors.
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Establish processes for evaluating training providers and training investments based on quality, completion, credential attainment, employment, wages, employer demand, and participant outcomes.
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Identify opportunities to expand training options while maintaining appropriate accountability for public workforce investments.
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Work with Business Intelligence and program staff to analyze training outcomes and inform policy and funding decisions.
Compliance, Monitoring & Risk Management
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Provide strategic oversight of Employ Milwaukee's WIOA and workforce development compliance functions.
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Directly supervise the Compliance Manager and provide strategic direction to compliance staff.
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Ensure federal, state, local, contractual, and organizational requirements are translated into clear and practical policies, procedures, and operational expectations.
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Establish a proactive compliance culture that identifies and addresses risk before it results in findings, questioned costs, performance deficiencies, or other adverse consequences.
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Ensure compliance monitoring, internal audits, external monitoring, corrective actions, and technical assistance are coordinated with program and performance management activities.
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Work with the Compliance Manager, WIOA Program Manager, CFO, Business Intelligence, and program leadership to address systemic compliance and performance issues.
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Review significant monitoring findings and determine appropriate organizational responses, corrective actions, policy changes, training, or program redesign.
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Ensure compliance information is translated into actionable guidance for managers, staff, service providers, vendors, and other partners.
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Oversee the organization's process for maintaining current policies and procedures related to workforce development programs and contracts.
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Ensure compliance and policy decisions appropriately balance regulatory requirements, organizational risk, operational efficiency, and participant and employer needs.
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Serve as a senior organizational leader for federal, state, local, and other funder monitoring activities related to WIOA and workforce development programs.
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Ensure Employ Milwaukee maintains systems and processes that support continuous monitoring readiness.
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Coordinate with the Compliance Manager, WIOA Program Manager, CEO, CFO, Business Intelligence, and other leaders to prepare for external monitoring.
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Review monitoring results and ensure findings, observations, and recommendations are translated into sustainable improvements.
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Identify recurring issues across funder monitoring, subaward monitoring, and internal reviews and develop organization-wide strategies to address root causes.
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Ensure corrective action plans are appropriately developed, implemented, documented, and monitored to completion.
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Identify opportunities to use monitoring results as a source of organizational learning and program improvement.
Contracts, Procurement & Governance
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Provide strategic leadership for procurement, compliance, monitoring, audit readiness, and risk management activities.
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Supervise the Compliance Manager and ensure regulatory requirements are translated into practical policies, procedures, and operational practices.
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Oversee corrective actions, monitoring activities, internal controls, and risk mitigation strategies to ensure compliance with federal, state, local, and contractual requirements.
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Promote a culture of accountability, continuous improvement, and responsible stewardship of public resources.
One-Stop Operator and American Job Center System
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Provide strategic leadership for Employ Milwaukee's role in the American Job Center and broader workforce development system.
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Oversee strategies related to the One-Stop Operator and American Job Center Memoranda of Understanding and related workforce system agreements.
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Ensure MOUs and system agreements clearly establish partner roles, responsibilities, resource commitments, referral processes, shared expectations, and accountability.
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Work collaboratively with workforce system partners to improve coordination, reduce duplication, strengthen referrals, and improve the customer experience.
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Identify opportunities for greater integration among WIOA partners and other workforce, education, human services, and economic development systems.
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Represent Employ Milwaukee in system-level discussions regarding American Job Center operations, service coordination, resource allocation, and workforce system strategy.
WIOA Planning, Performance, and Data Strategy
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Lead or provide strategic direction for development, implementation, modification, and annual review of Employ Milwaukee's WIOA Local and Regional Plans.
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Translate labor market information, employer feedback, policy developments, participant outcomes, and program performance into WIOA strategy and planning recommendations.
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Work with Business Intelligence and program leadership to establish performance dashboards and analytical tools that support decision-making.
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Regularly review WIOA performance indicators and direct strategies to improve outcomes.
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Ensure performance management emphasizes meaningful outcomes, including measurable skills gains, credential attainment, employment, training-related employment, wages, retention, and advancement.
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Identify trends and disparities in participant outcomes and develop strategies to address performance gaps.
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Use data to assess the effectiveness and return on investment of training, supportive services, work-based learning, and employer strategies.
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Ensure data and performance information are accessible and understandable to program managers, executives, Board members, and other stakeholders.
Cross-Organizational Strategy and Innovation
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Serve as a strategic connector among WIOA programs, Industry Programs, Business Solutions, Business Intelligence, Finance, Planning, Development, Communications, Community Engagement, and other Employ Milwaukee functions.
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Identify opportunities to braid funding and resources across WIOA and non-WIOA programs to expand services and improve outcomes.
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Lead cross-functional initiatives designed to improve operational efficiency and participant and employer outcomes.
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Identify opportunities to leverage technology, automation, artificial intelligence, data, and other innovations to improve workforce system operations.
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Develop strategies that reduce administrative burden while maintaining compliance and accountability.
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Promote organizational learning by identifying successful practices and creating systems to replicate and scale them.
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Serve as a strategic thought partner to the CEO on workforce system design, policy, funding, compliance, contracts, and program performance.
Leadership and Staff Development
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Provide leadership, coaching, supervision, and accountability to the WIOA Program Manager, Compliance Manager, and assigned staff.
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Establish clear performance expectations that align individual and team responsibilities with organizational strategy and participant and employer outcomes.
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Develop managers' capacity to lead complex programs, solve problems, manage performance, and implement strategic initiatives.
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Foster a culture of accountability, innovation, collaboration, continuous improvement, and professional excellence.
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Ensure staff understand the relationship between compliance requirements, operational decisions, participant outcomes, and employer value.
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Support professional development, succession planning, cross-training, and knowledge transfer among WIOA and compliance staff.
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Encourage managers to identify opportunities for innovation while maintaining appropriate controls and accountability.
Other Duties
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Prepare reports, presentations, policy analyses, recommendations, briefing materials, and other documents for the CEO, Executive Leadership Team, Board of Directors, committees, funders, government agencies, and external stakeholders.
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Maintain current knowledge of workforce development policy, labor market trends, workforce funding, program models, regulations, and emerging issues.
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Participate in organizational planning, leadership meetings, conferences, seminars, training, and other activities necessary to fulfill the responsibilities of the position.
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Travel locally, statewide, regionally, and nationally as required.
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Perform other duties as assigned.
An individual in this position must be able to successfully perform the essential duties and responsibilities listed above. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
Supervisory Responsibilities:
Directly supervises the WIOA Program Manager, Compliance Manager, and other staff as assigned.
KEY ABILITIES, KNOWLEDGE AND SKILLS:
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Strategic leadership and organizational management.
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Workforce development policy and WIOA expertise.
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Regulatory interpretation, compliance, and risk management.
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Program performance, data analysis, and continuous improvement.
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Contracting, procurement, and grant administration.
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Employer engagement and workforce system partnership development.
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Project management, facilitation, negotiation, and consensus building.
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Executive communication, public speaking, and stakeholder engagement
MINIMUM QUALIFICATIONS:
Bachelor’s degree in Political Science, Economics, Urban Planning, Business, History, Social Sciences, Public Administration, or a closely related field.
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A minimum of seven (7) years of progressively responsible professional experience in workforce development, public policy, government relations, program administration, grant management, strategic planning, compliance, or a related field.
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Demonstrated experience interpreting and applying federal, state, and/or local laws, regulations, policies, funding requirements, and contractual requirements.
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Demonstrated experience developing and implementing strategic initiatives, policies, programs, or organizational improvements involving multiple stakeholders or departments.
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Demonstrated knowledge of WIOA Title I-B programs and the public workforce development system, including workforce training, performance accountability, and employer engagement.
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Demonstrated ability to analyze complex information, identify policy and operational implications, and develop clear recommendations for senior leadership and other decision-makers.
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Demonstrated ability to effectively represent an organization in local, state, and national meetings, conferences, policy discussions, and other public forums.
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Equivalent combinations of education and experience that provide the knowledge, skills, and abilities necessary to successfully perform the essential functions of the position may be considered.
PREFERRED QUALIFICATIONS:
Professional experience working in a state or federal government agency, particularly in workforce development, economic development, labor, education, public policy, grants administration, or a related area.
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Experience working directly with state or federal legislative bodies, policymakers, government officials, or regulatory agencies on policy, funding, or workforce issues.
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Experience developing, interpreting, or implementing WIOA policies, state or federal workforce guidance, legislation, regulations, or grant requirements.
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Experience leading or managing WIOA Title I-B programs, workforce development initiatives, or other publicly funded workforce programs.
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Experience with government contracting, subaward management, procurement, monitoring, compliance, or grant administration.
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Demonstrated experience using labor market information, workforce data, performance metrics, and economic trends to inform policy and strategic decision-making.
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Experience representing an organization in statewide or national workforce associations, policy forums, conferences, legislative discussions, or other external leadership settings.
PHYSICAL AND MENTAL DEMANDS:
The mental and physical requirements described here are representative of those that must be met by an individual to successfully perform the essential functions of this position. While performing the duties of this job, the employee is frequently required to sit, talk and/or hear, and/or use hands to finger, handle, or touch objects, tools, or controls. The employee is occasionally required to stand and/or walk. The employee must occasionally lift and/or move up to 20 pounds while moving files, program materials, supplies, or small packages. Specific vision abilities required by this job include close vision and the ability to adjust focus.
WORKING ENVIRONMENT:
Work is performed in an office, classroom, educational, employer, community, and/or program-site environment. The noise level may vary from moderate to high depending on the program setting. The employee may occasionally be required to work outside of the typical office setting and travel locally to schools, employer locations, community organizations, field trip locations, partner institutions, and Camp RISE sites. Occasional evening and weekend work may be required in connection with youth services events, fundraising activities, employer engagements, and summer programming. This position may support Camp RISE programming at multiple locations and therefore requires the ability to travel locally and work in a variety of youth-serving environments.
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I have read and understand the duties, responsibilities, and requirements for this position. *
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Employee Acknowledgement Date
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- This document does not create an employment contract, implied or otherwise, other than an "at-will" employment relationship. Employ Milwaukee retains the discretion to add duties or change the duties of this position at any time.