Senior Associate - Strategic Finance

Position Description

The Senior Associate - Strategic Finance serves as Training The Street's FP&A lead and a cross-functional strategic partner for the business. This role will lead the company's financial planning, analysis, and forecasting processes while also contributing to operational and corporate initiatives that drive growth and long-term scalability. The Senior Associate - Strategic Finance works closely with the Chief Financial Officer and collaborates with leaders across all departments, maintaining full access to information and teams necessary to support informed, data-driven decision‑making.

Learning the skills of an operational CFO – this is a high‑impact and high‑visibility role with significant opportunity to combine finance and operations to make an impact at a global company.

This role combines traditional FP&A leadership with hands‑on partnership across key operational areas of the business.

• Lead the development and management of the annual operating plan, long‑term financial forecasts and rolling budgets, cash planning and covenant compliance.
• Build and maintain financial models, scenario analyses, and profitability frameworks to support decision‑making on strategic initiatives, capital allocation, and operational planning.
• Prepare and present executive‑level weekly and monthly financial reporting, including trends, variances, KPIs, and business drivers.
• Strengthen financial processes, tools, and analytics.
• Lead or support the evaluation and execution of potential mergers and acquisitions, including financial modeling, due diligence, strategic fit assessments, and integration planning.

• Partner with Account Management and Business Development leadership to assess pipelines, optimize sales performance, and evaluate the financial impact of new business activities.
• Collaborate with Technology and Infrastructure teams on major technology evaluations and decisions, investment analyses, and long‑term systems planning.
• Support People and Operations teams on organizational productivity analysis, new group structures, vendor and contract review, and cost‑management strategies.
• Opportunity to provide financial and strategic input on other corporate functions, including the company website and marketing, market strategy, and new initiatives.
• Develop and refine KPIs, dashboards, and reporting mechanisms to improve visibility into course economics, operational efficiency, and cost trends across the organization.

Location: Hybrid, New York, NY or Charlotte, NC Office

Department: Finance

Reports To: Chief Financial Officer

FLSA Status: Exempt

Supervisory Responsibilities: None at this time

• Prior experience in investment banking, corporate banking, FP&A, strategic finance, or similarly rigorous analytical roles.
• Advanced financial modeling skills, with a strong track record of building, maintaining, and owning complex models with a high degree of accuracy and discipline.
• Exceptional attention to detail and data integrity, with clear accountability for deadlines, outputs, and financial deliverables.
• Strong written and verbal communication skills, with the ability to translate complex financial analyses into clear, actionable insights for operational leaders and executives.
• Proven ability to partner cross‑functionally with technical, operational, and senior stakeholders in a fast‑paced environment.
• Bachelor's degree in Finance, Accounting, Economics, Business Administration, or a related field