Director, Strategic Finance & Capital Market

Job Description
WorldStrides is seeking a Director of Liquidity, Capital Planning & Strategic Finance to lead enterprise-wide cash flow forecasting, capital structure modeling, and liquidity risk management. This role will serve as the company’s center of excellence for cash, debt, and covenant analytics, supporting executive leadership, the Board of Directors, and external financing partners with high-quality models, insights, and materials.

This position plays a critical role in enabling disciplined growth, strengthening balance sheet visibility, and ensuring proactive management of liquidity and covenant considerations in a highly seasonal, working-capital-intensive business.

Job Responsibilities

Enterprise Cash Flow & Capital Structure Leadership

• Own and continuously enhance the company’s integrated three-statement, cash flow, and liquidity models, with increasing account-level detail and forecasting precision
• Model seasonal cash dynamics, including deposits, deferred revenue, working capital, and capital expenditures
• Develop and own detailed multi-tranche debt schedules (e.g., revolvers, term loans) and interest modeling
• Build pro forma capital structures to evaluate refinancings, growth initiatives, and strategic investments
• Own a rolling 13-week cash flow forecast to support near-term liquidity planning

Liquidity, Covenants & Risk Management

• Own a comprehensive covenant compliance and sensitivity model, including EBITDA definitions, add-backs, and downside scenarios
• Proactively identify and communicate liquidity and covenant risks, including clear scenario narratives and mitigation considerations
• Support lender reporting, data requests, and financing-related analyses, including amendment and refinancing support

Executive, Board & External Materials

• Prepare Board-level financial models, analyses, and presentations related to liquidity, capital structure, and strategic finance topics
• Produce lender-facing materials with a high standard of accuracy, clarity, and professionalism
• Support interactions with Investors and Lenders

Strategic Finance & Business Partnership

• Partner closely with FP&A and business leaders to translate volume, pricing, staffing, and cost drivers into cash flow and EBITDA implications
• Connect operational and strategic plans to long-term liquidity, covenant, and capital allocation forecasts
• Improve analytical rigor in cash flow and debt modeling
• Serve as a trusted advisor to senior leadership on liquidity risk, capital allocation trade-offs and downside scenarios by driving clear recommendations supported by clear analysis

M&A and Investment Analysis

• Build and evaluate acquisition, divestiture, and build-versus-buy models
• Assess purchase price, financing mix, synergies, operating leverage, payback, and value creation
• Integrate approved transactions into enterprise cash flow and debt models

Minimum Qualifications

• 4 years of experience in investment banking, strategic finance, FP&A, leveraged finance, or corporate development
• Advanced expertise in three-statement financial modeling, cash flow forecasting, and debt/capital structure modeling
• Experience proactively driving Board-level and Lender-facing financial analysis and presentations
• Strong ability to synthesize complex financial concepts into clear, actionable insights for senior leadership
• Advanced Excel and financial modeling skills; experience with modern FP&A, BI, or ERP tools is a plus
• Bachelor’s degree in Finance, Accounting, Economics, or a related field (MBA or CFA a plus)

What Success Looks Like

• Clear, trusted visibility into liquidity and covenant position across scenarios
• Faster, more confident executive decision-making around capital allocation and growth
• Strong partnership with Finance (FP&A, Accounting and Treasury) leadership, enabling sharper focus on core forecasting and business support
• This role provides unique exposure to Executive leadership, Board members and external investors
• Growth opportunities for more localized business strategic partnering

Work Perks:

• Fun & driven environment.
• Excellent medical, dental, and vision coverage, life, accidental death and dismemberment, accident, critical illness, and disability insurance, FSA healthcare, FSA dependent care, HAS with employer contribution, and generous 401k match.
• 10 paid floating corporate holidays, 1 paid volunteer day & 25 PTO days to start – accrue up to 28 over 3 years, 4 mental health days, and 5 bereavement days.
• Tuition reimbursement up to five thousand, two hundred fifty dollars annually or one thousand dollars towards professional certification annually.
• Opportunities for paid and discounted travel.
• Flexible work schedule providing on-site, remote, and virtual office opportunities.
• Encouraged participation in our Employee Resource Groups and Diversity, Equity, & Inclusion council.
• Fitness Center and café onsite at select locations.
• Employee Assistance Program (EAP)
• Paid Parental, Caregiver, and Disability leave.
• Team Member Discount Program.