Director, Strategic Finance & Capital Markets
Job Description
WorldStrides is seeking a Director, Strategic Finance & Capital Markets 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 strategic finance, FP&A, leveraged finance, or corporate development, including early career experience in private equity, or investment banking
Advanced expertise in three-statement financial modeling, cash flow forecasting, and debt/capital structure modeling and experience with modern FP&A, BI, or ERP tools
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
Comfort working in a fast-paced, high accountability environment with tight timelines and evolving priorities
Strong cross-functional partnering skills to drive informed decision-making across the organization
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:
Comprehensive health benefits: medical, dental, vision, life, AD&D, accident, critical illness, disability insurance, FSA/HSA options with employer HSA contributions, and a generous 401(k) match.
Generous paid time off including 11 paid company holidays, 25 PTO days the first year (prorated), 1 paid volunteer day, 4 mental health days, and bereavement
Professional development support, including up to $5,250 annually for tuition reimbursement and up to $1,000 for certifications annually
Opportunities for paid and discounted travel
Flexible work schedule providing on-site, remote, and hybrid office opportunities
Encouraged participation in a wide variety of Employee Resource Groups
Employee Assistance Program (EAP) and wellness resources, including fitness centers at select locations
Paid parental, caregiver, and disability leave
Team Member Discount Program
Engaging, collaborative, and fun work environment
The minimum and maximum full-time annual salaries for this role are listed below, by location. Please note that this salary information is solely for candidates hired to perform work within one of these locations, and refers to the amount WorldStrides is willing to pay at the time of this posting. Salaries for part-time roles will be prorated based upon the agreed upon number of hours to be regularly worked.
Candidates hired to work in other locations will be subject to the pay range associated with that location, and the actual annualized salary amount offered to any candidate at the time of hire will be reflected solely in the candidate’s offer letter.
California Salary Range
$140,000—$165,000 USD
The minimum and maximum full-time annual salaries for this role are listed below, by location. Please note that this salary information is solely for candidates hired to perform work within one of these locations, and refers to the amount WorldStrides is willing to pay at the time of this posting. Salaries for part-time roles will be prorated based upon the agreed upon number of hours to be regularly worked.
Candidates hired to work in other locations will be subject to the pay range associated with that location, and the actual annualized salary amount offered to any candidate at the time of hire will be reflected solely in the candidate’s offer letter.
Maryland Salary Range
$140,000—$165,000 USD
The minimum and maximum full-time annual salaries for this role are listed below, by location. Please note that this salary information is solely for candidates hired to perform work within one of these locations, and refers to the amount WorldStrides is willing to pay at the time of this posting. Salaries for part-time roles will be prorated based upon the agreed upon number of hours to be regularly worked.
Candidates hired to work in other locations will be subject to the pay range associated with that location, and the actual annualized salary amount offered to any candidate at the time of hire will be reflected solely in the candidate’s offer letter.
New York Salary Range
$140,000—$165,000 USD
The minimum and maximum full-time annual salaries for this role are listed below, by location. Please note that this salary information is solely for candidates hired to perform work within one of these locations, and refers to the amount WorldStrides is willing to pay at the time of this posting. Salaries for part-time roles will be prorated based upon the agreed upon number of hours to be regularly worked.
Candidates hired to work in other locations will be subject to the pay range associated with that location, and the actual annualized salary amount offered to any candidate at the time of hire will be reflected solely in the candidate’s offer letter.
Massachusetts Salary Range
$140,000—$165,000 USD
The minimum and maximum full-time annual salaries for this role are listed below, by location. Please note that this salary information is solely for candidates hired to perform work within one of these locations, and refers to the amount WorldStrides is willing to pay at the time of this posting. Salaries for part-time roles will be prorated based upon the agreed upon number of hours to be regularly worked.
Candidates hired to work in other locations will be subject to the pay range associated with that location, and the actual annualized salary amount offered to any candidate at the time of hire will be reflected solely in the candidate’s offer letter.
Virginia Salary Range
$140,000—$165,000 USD