Lead Business Systems Analyst

Goodwill Greater Milwaukee & Chicago • Milwaukee, WI

2d • Hybrid

About The Position

The Lead Business Systems Analyst serves as the strategic liaison between business leadership and the Technology department, converting high-level business asks into clear, actionable technology requirements that engineering teams can build and quality teams can validate. The role operates as a strategic partner to senior business leadership, ensuring alignment of technology initiatives to business strategy, operational priorities, and enterprise outcomes. The role pairs deep business curiosity with structured analytical inquiry to uncover the true intent behind a request, shape it into a defensible solution approach, and shepherd it through delivery to a tested, adopted outcome. The role owns alignment between business demand, enterprise technology direction, and portfolio prioritization, ensuring that technology investments maximize business value, manage risk, and scale across the organization. This role is deployed on Goodwill s highest-priority, most complex initiatives and operates with substantial independence. It carries hybrid accountability for business analysis, requirements authorship, project leadership, and quality assurance, while also influencing roadmap development, prioritization decisions, and enterprise capability planning. In addition to delivery accountability, the role contributes to technology roadmaps, long-term solution direction, and strategic planning efforts across business and IT leadership. Typically works on projects and initiatives that span 12 months- 2 years.

Requirements

• Two years of college education or experience equivalency, and a minimum of 7 years progressive experience in business analysis, systems analysis, or a comparable business / technology translation role.
• Bachelor s degree in Information Systems, Business Administration, Data / Analytics, or related field preferred.
• Demonstrated ability to elicit, document, and validate functional requirements, user stories, and data integration specifications that engineering teams can build directly from.
• Demonstrated experience partnering with senior business stakeholders to align technology initiatives with business strategy
• Proven ability to influence prioritization, roadmap planning, and decision-making
• Experience leading complex, cross-functional, enterprise initiatives
• Strong understanding of enterprise technology environments, including architecture, data, and integration.
• Project management experience leading complex, cross-functional initiatives end-to-end (12 24 months in scope); PMP, CAPM, IIBA CBAP/CCBA, or equivalent certification preferred.
• Working knowledge of QA testing practices, test strategy, test case authorship, UAT coordination, and defect triage, with willingness to deepen this capability on the job, or equivalent exposure to UAT coordination.
• Strong analytical and inquiry skills with comfort exploring data, processes, and edge cases to validate problem definition before recommending a solution.
• Proven facilitation and executive communication skills; able to translate fluently between business and technical audiences.
• Familiarity with modern enterprise platforms typical of Goodwill s portfolio (e.g., Microsoft 365, Dynamics, data warehouse / BI tooling, Copilot / AI-assisted workflows) preferred.

Nice To Haves

• Bachelor s degree in Information Systems, Business Administration, Data / Analytics, or related field
• PMP, CAPM, IIBA CBAP/CCBA, or equivalent certification
• Familiarity with modern enterprise platforms typical of Goodwill s portfolio (e.g., Microsoft 365, Dynamics, data warehouse / BI tooling, Copilot / AI-assisted workflows)
• Willingness to deepen QA capability on the job

Responsibilities

• Acts as a trusted advisor to senior business leadership, building partnerships to understand strategy, operational needs, and priorities.
• Leads intake, shaping, and prioritization of business demand, aligning work to enterprise technology direction and organizational capacity.
• Collaborates with business and IT leadership to develop and maintain technology roadmaps aligned to business outcomes, risks, and opportunities.
• Provides guidance on tradeoffs, prioritization, risks, and sequencing of initiatives.
• Ensures alignment between business strategy and enterprise technology direction across initiatives.
• Lead business discovery to uncover underlying intent, define root problems, establish measurable success criteria, and align technology work to business strategy and operational realities.
• Serve as a trusted advisor to business leaders by reframing ambiguous requests into clear problem statements, prioritized opportunities, and actionable initiatives aligned to enterprise strategy and roadmap direction.
• Translate business needs into engineering-ready requirements, user stories, acceptance criteria, specifications, and process documentation that support build, test, and delivery.
• Partner with architects, engineers, cybersecurity, and platform teams to confirm feasibility, manage scope, document assumptions and constraints, and support intake and prioritization of new work while ensuring alignment with enterprise architecture, data strategy, and long-term technology direction.
• Ensure solutions are scalable, sustainable, and aligned with enterprise standards and integration patterns.
• Lead technology delivery for high-priority, complex initiatives, owning scope, risks, dependencies, and key decision points while aligning work to broader business and technology priorities.
• Maintain clear communication, status reporting, decision-making forums, and release transition support to move work forward and prepare solutions for ongoing support.
• Lead solution validation by designing and executing test strategies, test cases, and UAT coordination across functional, integration, regression, and acceptance testing.
• Confirm delivered solutions meet business intent and release criteria, while strengthening QA capability over time through practical experience and targeted development.
• Identify technology trends, automation opportunities, and process improvements that increase business efficiency, including practical uses of AI and Copilot, while promoting consistent analysis and QA practices across the team.
• Contribute to and influence enterprise technology roadmaps, capability planning, and long-term solution direction
• Recommend technology investments, process improvements, and innovation opportunities that drive efficiency and business value
• Provide input into technology policies, standards, and practices that improve consistency across the organization
• May partner with coworkers to advance their development.
• May serve as a team member, or subject matter expert, for formal or department projects. Contributes ideas and helps develop solutions, while balancing demands of project work and routine job responsibilities. Engages effectively in change affecting her/him, communicating appropriately with supervisor. Follows through on learning, skill building, and practice necessary to adapt to change.
• Light supervision; works independently. Periodic review of work by manager or direct customer. Researches, analyzes, and evaluates situations and reports on findings. Solves advanced problems.
• Champions Goodwill s community engagement initiatives. Aware of Goodwill s community partner organizational and participates in volunteer opportunities as pertains to role and interest. Participates in industry/knowledge groups.
• Responsible for completing other duties / responsibilities as assigned.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior