Senior Director of Finance

Overview

This newly created role combines strategic financial leadership with hands-on responsibility across finance, accounting, reporting, forecasting, cash management, and finance strategy. Reporting to the Founder and CEO, the Senior Director of Finance will lead the finance function through a structured transition of responsibilities, projects, systems, and workflows.

The position will work closely with the Managing Director of Operations & Finance during the handoff and will oversee finance and accounting functions while partnering on shared priorities.

Responsibilities

Financial Leadership and Business Partnership

• Lead the finance function and help shape the organization’s next stage of growth through financial strategy, insights, and collaborative partnerships.
• Assume leadership of finance through a structured transition of responsibilities, projects, systems, reporting, and workflows.
• Meet weekly with the CEO and Managing Director of Operations to review financial performance, cash flow, forecasts, priorities, risks, and opportunities.
• Meet monthly and as needed with executive and division leaders to review division financial performance, forecasts, priorities, risks, and opportunities; provide actionable insights and guidance.
• Maintain a separate, ongoing weekly one-on-one meeting with the CEO for financial strategy, guidance, decision-making, and leadership alignment.
• Coordinate closely with Operations after the transition to support effective handoffs and shared priorities.
• Translate financial information into clear recommendations, identifying practical actions and explaining relevant tradeoffs.
• Evaluate the financial implications of internal hiring, new markets, service expansion, technology investments, and other strategic initiatives.
• Create monthly reporting and executive finance reporting, continually improving internal reporting and providing insights on monthly/annual growth and performance.
• Manage and partner with the Payroll and Accounting Manager and an Accounts Receivable/Finance staff member.

Accounting and Financial Reporting

• Own the accuracy, completeness, and timeliness of accounting records and financial reporting.
• Lead the monthly close, account reconciliations, accruals, and preparation of financial statements; partner with the Payroll and Accounting Manager to review and improve the GL reporting structure.
• Review financial reports before distribution and investigate discrepancies or unusual results.
• Establish a consistent reporting calendar and clear definitions for financial metrics.
• Develop company-wide and division-level reporting for revenue, gross profit, contribution profit, operating expenses, and operating results.
• Document expense allocations so leaders understand how shared costs affect reported performance.
• Coordinate with external accounting and tax professionals on tax preparation, year-end activities, and other financial matters.
• Strengthen internal ownership of financial reporting and reduce unnecessary reliance on outside providers.
• Work closely with the Accounting Manager and outside CPA firm to bring accounting services fully in-house.
• Perform hands-on accounting and transaction classification as needed; support QuickBooks system work as required to maintain accuracy.

Executive Dashboards and Financial Insights

• Create useful, accessible reporting to help executives make decisions and anticipate business needs.
• Improve or replace the weekly executive leadership team update with a reliable reporting process.
• Clearly distinguish accrued revenue, invoiced revenue, collections, and cash received.
• Provide weekly visibility into payroll obligations, staffing hours, invoicing, collections, gross profit, and significant exceptions.
• Deliver monthly financial results with comparisons to budget and forecast, explanations of material variances, and recommended actions.
• Identify trends and opportunities across divisions, service lines, clients, and other business segments.
• Continuously improve reporting based on the decisions leaders need to make.

Budgeting, Forecasting, and Growth Planning

• Develop the annual operating budget using historical placements, billings, gross margin, and recruiter productivity.
• Maintain rolling forecasts for permanent-placement fees, temporary staffing revenue, gross profit, operating expenses, EBITDA, and cash.
• Build a rolling 13-week cash forecast covering weekly payroll, payroll taxes, benefits, contractor payments, client collections, operating expenses, and borrowing needs.
• Evaluate hiring investments using expected ramp time, placement or gross-profit targets, productivity assumptions, and break-even requirements.
• Assess working capital and credit capacity needed to fund temporary payroll while waiting for client payments.
• Forecast financial impact of adding temporary workers, winning large accounts, entering new markets, or expanding service lines.
• Identify client, industry, and account concentration risks affecting revenue, margins, and cash flow.
• Partner with outside CPA firm to establish tax plan for quarterly estimated payments.

Payroll Finance and Commission Oversight

• Own financial management and oversight of payroll for internal employees, external temporary, and interim W-2 employees in collaboration with the Payroll and Accounting Manager.
• Work with Payroll and Operations to receive approved hours and required inputs; Payroll and Operations owns routine timesheet collection, approval coordination, and follow-up with employees and clients.
• Oversee payroll processing, financial validation, funding, payment accuracy, reconciliations, and correction workflows.
• Confirm approved pay rates, hours, commissions, deductions, and adjustments are accurately reflected in payroll; improve the payroll audit process.
• Establish payroll deadlines, approval responsibilities, exception procedures, and backup coverage.
• Coordinate with Operations and HR to resolve discrepancies promptly and support accurate, timely employee payments.
• Oversee payroll providers and verify completion of payroll tax deposits, filings, and reporting.
• Establish ownership of commission calculations, reconciliations, accruals, and payment controls.
• Model proposed commission and incentive changes to help leadership understand financial impact.

Staffing Costs, Pricing, and Profitability Tools

• Maintain accurate, regularly updated employment burden models for core states and other applicable locations.
• Incorporate employer payroll taxes, workers’ compensation, benefits, and other employment costs with documented assumptions.
• Provide practical pricing tools to support understanding of pay rates, bill rates, markup, gross margin, and contribution profit.
• Identify differences between estimated and actual employment costs and update models accordingly.
• Analyze profitability across temporary staffing, interim services, direct hire recruiting, and retained executive search.
• Identify margin leakage, billing discrepancies, unbilled revenue, and other improvement opportunities.
• Help leaders evaluate client pricing and contract terms in collaboration with Operations and appropriate advisers.

Cash Management, Billing, and Receivables

• Establish internal controls and oversee cash management, accounts payable, billing controls, and accounts receivable reporting.
• Maintain visibility into overdue balances, collection activity, disputed invoices, client concentration, and credit exposure.
• Partner with client-facing leaders and Operations to resolve billing issues and improve collection workflows.
• Monitor the relationship between payroll commitments, client payment timing, and available funding.
• Prepare, review, reconcile, and distribute required bank/funding-provider reports on schedule.
• Evaluate banking and funding costs and recommend improvements supported by a clear business case.

Systems, Controls, and Internal Capabilities

• Complete a comprehensive assessment of finance systems, processes, controls, staffing, and reporting.
• Develop and implement a prioritized improvement plan to increase efficiency, reduce errors, and support growth.
• Improve information flow among QuickBooks, payroll, billing, Bullhorn, and reporting systems, as applicable.
• Use technology and automation to reduce repetitive work and strengthen accuracy.
• Establish documented procedures, access controls, payment approvals, independent reviews, and continuity plans.
• Ensure essential workflows have trained backup coverage.
• Evaluate opportunities to bring additional accounting, reporting, and payroll activities in-house.
• Assess payroll processing and payroll funding as separate but connected decisions.
• Present a transition business case addressing provider fees, software, staffing, implementation costs, working capital, controls, and service continuity.
• Lead approved changes through a phased implementation plan with clear readiness criteria.

Finance Team Leadership

• Lead, coach, and develop a lean accounting and finance team while staying actively involved in day-to-day work.
• Establish clear responsibilities, priorities, performance expectations, and service standards.
• Evaluate department capacity and recommend team structure changes as needed.
• Hire and develop additional finance or accounting support when approved and supported by business needs.
• Foster a collaborative environment where questions are welcomed, issues are raised early, and accuracy matters.
• Build strong working relationships across the organization and communicate financial information in a useful, approachable way.

Tax Planning, Compliance, and CPA Coordination

• Coordinate with CPAs for timely S-corporation federal, state, and local filings.
• Prepare quarterly tax projections, payment schedules, and required supporting documents.

Required Qualifications

• At least 10 years of progressively responsible finance and accounting experience.
• At least three years of experience leading and developing others.
• Experience leading a small finance team while personally performing detailed accounting and analytical work.
• Demonstrated command of accounting, financial statements, reconciliations, accruals, budgeting, forecasting, and cash management.
• Strong QuickBooks proficiency and advanced spreadsheet and financial modeling skills.
• Experience processing and overseeing multi-state payroll and related financial workflows (must include California).
• Demonstrated success improving reporting, systems, processes, or financial controls.
• Examples of helping a company grow, improve profitability, strengthen cash flow, or make informed investment decisions.
• Strong technology skills and ability to learn, evaluate, and improve financial systems.
• Excellent organization, attention to detail, follow-through, and problem-solving skills.
• Ability to communicate clearly with executives, managers, employees, and outside partners.
• Sound judgment, discretion, and commitment to protecting confidential financial and employee information.
• Optimistic, collaborative leadership style with confidence, initiative, and accountability.
• Ability to work onsite in the Portland, OR region on Tuesdays and Thursdays a plus.

Preferred Qualifications

• Experience in staffing, recruiting, executive search, employer-of-record services, or another payroll-intensive multi-state business.
• Experience with payroll funding, receivables financing, and working capital planning.
• Familiarity with staffing burden calculations, client pricing, commission structures, and division-level profitability.
• Experience supporting a company through significant growth or increasing financial complexity.
• Experience bringing outsourced financial activities in-house or leading financial system transitions.
• A relevant degree, CPA, CMA, or comparable professional expertise.

Compensation & Benefits

• Anticipated starting salary range: $150,000–$200,000 annually, depending on experience, qualifications, and demonstrated expertise.
• Room for professional title growth and long-term potential path to CFO.
• Fully paid individual health, dental, vision, life insurance, short- and long-term disability.
• 80 hours of fully paid parental leave.
• Annual reviews and annual raises.
• Career growth and continued training opportunities.
• Paid Time Off: Fourteen (14) Paid Time Off days in year one; amount increases with tenure.
• Paid holidays: Eleven (11).
• Wellness and community time: One (1) paid wellness day + two (2) paid community volunteer days.
• Paid birthday: take your birthday off, or another day within a week of your birthday.
• Separate bank for Paid Sick Leave.
• 401(k) + employer contribution.
• Monthly cell phone and internet stipend.
• Remote work flexibility with options for virtual team connection.

Location & Schedule

• Location: Portland, Oregon region or remote US.
• Schedule: Full-time.
• Fully remote work within the U.S. may be considered for highly qualified candidates.
• Local candidates available for limited in-office finance work on Tuesdays or Thursdays a plus.