Controller

Head Of The Charles Regatta•Cambridge, MA

40d•$130,000 - $150,000•Hybrid

About The Position

The Head Of The Charles Regatta (HOCR) is the largest rowing event in the world and Boston’s second-largest sporting event. Each October, more than 12,000 athletes and 375,000 spectators gather along the Charles River for a three-day celebration of sport, community, and excellence. In addition to race weekend, HOCR operates a growing portfolio of year-round programs and initiatives. We are seeking an experienced, highly capable Controller to lead the organization’s day-to-day financial management. This is a senior, hands-on role ideal for a seasoned nonprofit or event-focused finance professional who thrives in a lean organization, operates with a high degree of autonomy, and brings both rigor and pragmatism to financial operations. The Controller is the senior financial leader responsible for the day-to-day financial management, controls, and sustainability of the Head Of The Charles Regatta, a complex nonprofit sporting event organization with a highly seasonal operating cycle. This role is well-suited for an experienced Controller from a nonprofit, National Governing Body (NGB), sports organization, or event-driven environment who brings deep accounting expertise, strong operational judgment, and the ability to operate independently in a lean organization. The Controller serves as the organization’s primary steward of financial accuracy, discipline, and risk management, while also acting as a strategic thought partner to senior leadership. The Controller oversees budgeting, forecasting, accounting, cash management, audit and compliance, payroll and benefits, and financial controls across both race weekend and year-round programs. This role requires a hands-on leader who is comfortable owning the details while maintaining a clear view of the broader financial picture, anticipating issues, and proactively advising leadership. The Controller works closely with the Executive Director and Board leadership, and serves as a standing member of the Finance Committee. While this is not a traditional CFO role, it is a senior position with significant autonomy, visibility, and influence, requiring minimal day-to-day oversight and a high degree of professionalism, judgment, integrity and self-direction.

Requirements

Bachelor’s degree in Accounting, Finance, Business, or related field; CPA or equivalent experience strongly preferred.
15+ years of progressive accounting or financial management experience, ideally within a nonprofit, event-based, or complex operating environment.
Demonstrated experience owning budgeting, forecasting, audit management, and financial reporting end-to-end.
Strong knowledge of nonprofit accounting standards and compliance requirements.
High level of comfort working independently with minimal supervision in a small organization.
Exceptional attention to detail paired with the ability to think strategically and communicate clearly.
Experience working with Boards and Finance Committees.
Proficiency with accounting systems (QuickBooks preferred), spreadsheets, and financial modeling.
Strong organizational, communication, and prioritization skills.

Nice To Haves

Experience in or affinity for sports, live events, or mission-driven organizations is a plus; passion for rowing welcome but not required.

Responsibilities

Own the organization’s day-to-day financial operations, ensuring accuracy, timeliness, and transparency.
Oversee all accounting functions, including general ledger, journal entries, reconciliations, and monthly close.
Manage accounts payable and receivable processes, overseeing the part-time bookkeeper and interfacing with the commercial team
Maintain and continuously improve financial systems, controls, and documentation.
Ensure compliance with nonprofit accounting standards and best practices.
Lead the annual budgeting process, including multi-scenario budgeting and venue-level profitability analysis.
Work with the Finance and Investment committee and, as appropriate, external managers, to maintain and grow the HOCR Endowment fund
Maintain rolling forecasts throughout the year, with particular focus on the Regatta planning cycle.
Provide regular financial reporting to the Executive Director, Finance and Investment Committees, and Board of Directors.
Develop clear, decision-oriented financial models and dashboards to support leadership planning.
Support year-round initiatives and special events with project-based budgets and financial analysis.
Lead the modernization of financial systems, tools, and analytical capabilities to improve efficiency, visibility, and decision-making
Serve as the primary lead for the annual external audit, ensuring a smooth, timely process.
Oversee preparation and filing of all required tax and regulatory filings, including Form 990 and Massachusetts Form PC.
Maintain audit-ready documentation and financial models to support an efficient year-end close.
Coordinate with external auditors, tax advisors, and regulators as needed.
Oversee payroll processing, benefits administration, and retirement plans (401K and 403(b), ensuring accuracy and compliance.
Manage cash flow, reserves, and short-term liquidity planning across the annual event cycle.
Monitor banking relationships and cash controls.
Provide thoughtful guidance on compensation, benefits, and financial sustainability in partnership with leadership.
Oversee insurance coverage, risk management practices, and compliance requirements.
Support financial aspects of permits, public safety coordination, and vendor contracts as needed.
Partner cross-functionally with Operations, Commercial, and Development teams to ensure financial alignment with execution.
Serve as a standing member of the HOCR Finance Committee.
Support longer-term financial planning, scenario analysis, and organizational growth initiatives.
Contribute to Board materials, presentations, and strategic discussions.
Partner closely with the Executive Director as a trusted financial advisor.