AAI - VP, Financial Systems

Overview Alera Group is seeking a Vice President, Financial Systems to serve as the enterprise leader responsible for the vision, strategy, and performance of the Workday Financial Management platform and broader financial systems ecosystem. Alera Group was founded in 2017 and has grown to become the 14th largest broker of US business. We are passionate about our clients’ success in the areas of Employee Benefits, Property and Casualty Insurance, Retirement Plan Services, and Wealth Services. With a network of offices nationwide, our commitment to collaboration allows us to offer national resources combined with local service. Responsibilities Reporting to the CIO, this executive will drive the transformation and optimization of financial systems to support business growth, acquisitions, regulatory compliance, and data-driven decision-making. This role operates as the enterprise platform owner, accountable for delivering measurable business value through system strategy, governance, and continuous improvement. The ideal candidate brings a strong blend of finance domain expertise, technology leadership, and enterprise transformation experience, with the ability to partner across Finance, HR, and IT to deliver scalable, integrated solutions. Enterprise Platform Strategy & Ownership Own the enterprise vision, strategy, and multi-year roadmap for Workday Financial Management and the broader finance technology ecosystem Serve as executive product owner for Workday Financials, with accountability for platform performance, scalability, and value realization Drive measurable improvements in financial operations, including close cycle efficiency, reporting accuracy, and system adoption Lead automation, integration, and data strategy to improve speed, transparency, and decision-making across Finance Finance & Executive Partnership Partner with the CIO, CFO, Controller, and FP&A leadership to define and execute finance transformation strategy Align technology investments with business priorities, growth initiatives, and operational efficiency goals Provide executive-level insight into system capabilities, risks, and investment decisions Operating Model & Governance Define and own the financial systems operating model, including governance structures, decision rights, and prioritization frameworks Establish scalable processes for intake, roadmap planning, and delivery across Finance and IT Ensure alignment of system architecture, data models, and controls across the enterprise CHRO Partnership & Workday Platform Partner with the Chief Human Resources Officer (CHRO) as a co-owner of the Workday platform across Financial Management and Human Capital Management (HCM) Ensure integrated data architecture and seamless workflows across Finance, Payroll, Recruiting, and HR systems Align governance, security, and compliance practices across Finance, HR, and Legal stakeholders Support enterprise initiatives including workforce analytics, compensation processes, and HR transformation M&A Integration Leadership Serve as executive owner for financial systems integration during mergers and acquisitions Lead onboarding of acquired entities into Workday Financials, including chart of accounts, worktags, controls, and reporting Partner with Corporate Development, Finance, HR, and IT to execute repeatable integration playbooks Ensure post-acquisition stabilization, compliance, and continuity of financial reporting Identify opportunities to accelerate synergy capture through system standardization and automation Global Delivery & Vendor Management Define and execute a global delivery model leveraging onshore, offshore, and managed service providers Establish governance, performance metrics, and communication frameworks for distributed teams Own vendor strategy, contract negotiations, and performance management across implementation partners and system providers Budget & People Leadership Full accountability for financial systems operating and capital spend, including forecasting, cost optimization, and ROI tracking Authority to approve system investments and transformation initiatives within governance thresholds Lead a Financial Systems organization of 5–10 direct team members, including managers, analysts, and architects, with oversight of extended offshore and vendor teams Drive organizational design, workforce planning, and leadership development within the function Qualifications Bachelor’s degree in Finance, Accounting, Business, Information Systems, or related field 12+ years of experience leading enterprise financial systems and large-scale transformation initiatives Deep expertise with Workday Financial Management and strong working knowledge of Workday HCM, Payroll, and Recruiting Strong understanding of accounting processes, financial close, reporting, internal controls, and audit requirements Proven experience operating in acquisitive or private equity-backed organizations preferred Demonstrated ability to lead cross-functional teams and influence executive stakeholders Preferred Skills & Experience Workday Financials and/or Workday HCM certification preferred Experience building and scaling global delivery models, including offshore teams and managed services Strong background in ERP transformation, integrations, and enterprise data strategy Experience with vendor management, contract negotiation, and large-scale system implementations Ability to operate in a fast-paced, high-growth, multi-entity environment Additional Information Compensation: Salary range: $225,000 – $280,000 per year, based on applicant's education, experience, skills and abilities.Eligible for performance-based bonus: Yes Benefits: Aleraa Group offers comprehensive benefits including medical, dental, vision, life and disability coverage, 401(k), generous PTO, and more. Work Model: This role is Remote We're an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class. Aleraa Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process. #LI-NO1 #LI-Remote