Director, Strategic Finance & Capital Market

WorldStrides

2d•Hybrid

About The Position

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.

Requirements

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)

Responsibilities

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
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
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
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
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

Benefits

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.