Director of Financial Transformation

The Baldwin Group•Tampa, FL

About The Position

The Director, Financial Systems Transformation is a senior people-leader responsible for modernizing, optimizing, and scaling Baldwin’s accounting and finance systems to support growth, operational rigor, and regulatory compliance. This role blends financial expertise with systems transformation leadership, owning enterprise-wide improvements across processes, data governance, reporting, controls, and the Workday Financials ecosystem. Additionally, this role leads a team of managers and senior professionals, translates enterprise strategy into an executable transformation roadmap, and partners with executive leadership across Finance, Technology, and the business to deliver sustainable change. Position Summary The Director, Financial Systems Transformation is a senior people-leader responsible for modernizing, optimizing, and scaling Baldwin’s accounting and finance systems to support growth, operational rigor, and regulatory compliance. This role blends financial expertise with systems transformation leadership, owning enterprise-wide improvements across processes, data governance, reporting, controls, and the Workday Financials ecosystem. Additionally, this role leads a team of managers and senior professionals, translates enterprise strategy into an executable transformation roadmap, and partners with executive leadership across Finance, Technology, and the business to deliver sustainable change.

Requirements

Advanced knowledge of U.S. GAAP and internal control frameworks (e.g., COSO), with strong subject-matter expertise in financial systems, general ledger and subledger design, and financial close processes.
Deep hands-on expertise with Workday Financials implementation and optimization (or comparable ERP), including configuration, integrations, reporting, and security model design.
Strong internal control and compliance expertise, including SOX-aligned control design, testing, remediation, and audit readiness across financial systems and processes.
Expertise in monthly close and reporting operations, including reconciliations, journal entries, variance analysis, data validation, and system-supported reporting.
Advanced financial analytics and data governance capabilities; experience building and leading teams that work with complex data models, KPIs, and BI/analytics tools.
Leadership and people-management skills, including goal setting, coaching, performance management, talent development, and hiring/separation authority at the manager and senior-professional level.
Proven ability to lead large, cross-functional initiatives and influence senior stakeholders across Finance, Technology, and business units.
Strong communication and stakeholder-influence skills, with the ability to explain complex systems and accounting matters to non-technical partners and drive cross-functional alignment.
Analytical problem-solving ability, with sound judgment in ambiguous situations and capacity to design scalable, sustainable process and systems improvements.
Ability to manage competing deadlines, deliver a fast, high-quality close and reporting environment, and drive continuous improvement in processes and systems.
High ethical standards and professional skepticism, with strong attention to detail and commitment to accuracy and control.
Bachelor’s degree in accounting, finance, information systems, or related field; CPA designation required.
10+ years of progressive accounting/finance experience, including significant experience in insurance brokerage or closely related financial services; and at least 5 years of formal people-leadership experience leading managers and/or senior professionals in a complex, multi-entity environment.
Direct experience leading accounting/finance transformation initiatives and major ERP/financial systems projects (preferably Workday Financials).
Proven track record strengthening internal controls and supporting audits in a SOX or comparable control environment.
Experience in publicly traded or large multi-entity organizations undergoing rapid growth or transformation preferred.
Background in financial systems integration or ERP modernization, including AI and automation use cases for Finance, preferred.
Formal training or certifications in change management, project/program management, or process improvement (e.g., Prosci, PMP, Lean Six Sigma) preferred.

Nice To Haves

Experience in publicly traded or large multi-entity organizations undergoing rapid growth or transformation preferred.
Background in financial systems integration or ERP modernization, including AI and automation use cases for Finance, preferred.
Formal training or certifications in change management, project/program management, or process improvement (e.g., Prosci, PMP, Lean Six Sigma) preferred.

Responsibilities

Set team vision, goals, and performance standards; allocate work, provide coaching and feedback, and build succession depth across financial systems and transformation roles.
Translate enterprise and Finance objectives into a multi-year financial systems and process transformation roadmap aligned with growth, control, and regulatory requirements; monitor execution and adjust plans as needed.
Define the target-state architecture and operating model for accounting and finance processes, emphasizing scalability, standardization, and strong internal controls.
Serve as business owner for Workday Financials and related finance technology, accountable for system strategy, roadmap, and value realization.
Direct teams that partner with IT, Data, and business stakeholders to enhance integrations, chart of accounts design, reporting structures, and data architecture.
Establish and govern standards for configuration, change management, testing, and user access/security across financial systems.
Oversee redesign of end-to-end accounting and finance processes (e.g., record-to-report, order-to-cash, procure-to-pay, commission and carrier settlements) to reduce manual work, strengthen controls, and improve cycle time.
Champion the use of AI, automation, and workflow tools to eliminate manual reconciliations, improve data quality, and reduce operational risk.
Design, maintain, and monitor internal controls across financial systems and processes, including SOX-relevant areas; remediate deficiencies and implement preventive controls in partnership with Accounting and Internal Audit.
Ensure audit-ready evidence, documentation, and system configurations to support internal and external audits, regulatory exams, and control testing.
Build and oversee a financial data framework that supports forecasting, analytics, and executive decision-making across the enterprise; ensure consistency of definitions and data usage across entities and platforms.
Direct development of scalable dashboards, KPIs, and self-service reporting aligned to insurance brokerage performance metrics (e.g., revenue, commission, retention, carrier economics).
Apply deep knowledge of brokerage-specific accounting (revenue recognition, commission structures, contingent revenue, carrier payables/receivables, multi-entity consolidations) to system and process design.
Identify and prioritize transformation opportunities unique to brokerage operations (e.g., producer compensation, carrier settlements, fee and commission arrangements) and embed them into the roadmap.
Partner with Accounting, FP&A, business segment leaders, and Technology to align commercial terms, system configurations, and financial policies with the designed control and reporting environment.
Represent Financial Systems Transformation in steering committees and governance forums; communicate risks, dependencies, and trade-offs with clear, practical recommendations.
Communicate complex financial systems and control topics in accessible terms to executive and non-technical stakeholders, driving alignment and adoption of new ways of working.