Manager, Stock Program & Payroll

Position Summary:

Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them.

In the Manager, Stock Program & Payroll position, you'll lead the administration and continued evolution of Direct Supply's equity and stock programs while providing oversight of payroll operations. You'll ensure accurate, compliant, and efficient execution across both areas, partnering closely with Finance, HR, Legal, and external providers to deliver an exceptional Partner experience. With the stock program as your primary focus, you'll combine financial and accounting expertise, leadership, technology, and an AI-first mindset to strengthen controls, improve processes, and scale these critical programs.

Skills Needed:

• Set Direction & Strategy - Define where we are heading, why it matters, and what is needed to achieve results. Turn ambiguity into clear priorities and connect day-to-day work to strategy. Use a whole-system view to balance customer, business, capability, and long-term implications and focus teams on the highest-impact opportunities.

• Exercise Judgment & Own Decisions - Navigate complex, cross-system tradeoffs involving business outcomes, risk, speed, and long-term impact. Use critical thinking to determine where human review or escalation is required, challenge assumptions, and take ownership for results and decisions.

• Design & Scale Work Systems - Design how people, processes, decisions, data, technology, and AI work together. Redesign workflows, clarify roles and decision rights, remove friction, create feedback loops, and build scalable work systems that improve the whole system for quality, speed, customer experiences, and results at scale.

• Mobilize Leaders & Teams - Align leaders, stakeholders, and teams across functions, dependencies, and competing priorities. Build commitment to shared outcomes, navigate dynamics, remove systemic barriers, and drive coordinated execution and transformational change.

• Lead & Build Capability - Engage, develop, and recruit top talent with domain depth, systems thinking, AI fluency, and the adaptability needed for the future. Create the context, coaching, feedback, tools, accountability, and culture that enable people and systems to raise the bar and scale impact over time.

What You'll Do and Impact:

• Own and lead the day-to-day administration of Direct Supply's equity and stock programs, ensuring accurate, timely, and compliant execution of grants, vesting events, exercises, participant transactions, and recordkeeping.

• Maintain the integrity of equity data and systems while partnering with Finance, HR, Legal, Payroll, and external providers to ensure seamless program administration, reporting, and compliance.

• Manage equity-related accounting activities, including journal entries, reconciliations, stock-based compensation accounting, and support for monthly and quarterly close processes.

• Ensure appropriate accounting treatment of equity awards, including compliance with ASC 718 and applicable tax, regulatory, audit, financial reporting, and internal policy requirements.

• Oversee payroll operations, including payroll review, forecasting, controls, issue resolution, and continuous improvement to support accurate and timely payroll administration.

• Ensure effective coordination between equity and payroll processes to support accurate tax withholding, reporting, and processing associated with equity transactions.

• Serve as a trusted resource for Partners by providing education, guidance, and support related to equity programs, processes, and tools while fostering a positive Partner experience.

• Prepare and analyze equity program reporting, stock-based compensation forecasts, payroll forecasts, balances, and trends to provide actionable insights that support financial planning and decision-making.

• Identify and implement opportunities to strengthen controls, streamline workflows, automate manual processes, and improve the accuracy and scalability of stock program and payroll operations.

• Lead enhancements to equity management systems and integrations across equity, payroll, HRIS, and financial platforms to improve data integrity and operational effectiveness.

• Leverage AI, automation, and emerging technologies to enhance administration, reporting, analysis, and decision-making while thoughtfully evaluating where technology can create meaningful business value.

• Partner across the organization to continuously evolve stock program and payroll operations in response to changing business, regulatory, technology, and Partner needs.

Experience:

• Bachelor's degree in Finance, Accounting, Business, Human Resources, or related field.

• 8+ years of experience in equity compensation administration, stock plans, accounting, finance, payroll, total rewards, or related operational functions.

• Experience administering equity programs and supporting stock-based compensation accounting, financial reporting, audits, regulatory compliance, and tax-related requirements.

• Experience overseeing or supporting payroll operations, processes, controls, forecasting, and issue resolution.

• Experience partnering cross-functionally with Finance, HR, Legal, Payroll, and external service providers.

• Proficiency with equity management platforms, financial systems, and advanced Microsoft Excel.

• Experience leveraging technology, automation, system integrations, AI-enabled tools, and data analysis to improve operational efficiency, controls, and reporting.

Additional Items of Interest:

• Certified Equity Professional (CEP) designation.

• Experience with equity management platforms such as Carta, Shareworks, Fidelity, E*TRADE, Morgan Stanley, or similar systems.

• Experience in a private, pre-IPO, or high-growth company environment.

• Familiarity with integrations across equity administration, payroll, HRIS, and financial systems.

• Experience using AI-enabled tools, automation platforms, or reporting technologies to improve finance, equity, or payroll operations.

Job Details:

• Location: Milwaukee, WI