Head of Financial Planning & Analysis

Tradewind Group (the “Company”) is a Hawaiʻi-based company that invests in and operates businesses across real estate and private equity, technology services, and insurance. Our Company promotes the ownership and growth of local businesses, is firmly committed to developing local expertise and talent, and works alongside our partners to improve the well‑being of Hawai‘i. We provide services and make investments that produce good financial returns while supporting the needs of the community and doing our part to preserve what is special about Hawai‘i and its people.

Role Description

Reporting to the VP & CFO, the AVP, Financial Planning & Analysis ("FP&A") leads the strategic and financial planning function for Tradewind Group and its subsidiaries. As an investment management organization, we expect this role to bring both the discipline of a corporate FP&A leader and the analytical rigor of an investment professional — translating data into a clear, defensible point of view that drives capital allocation, performance management, and executive decision‑making.

The AVP owns enterprise‑wide budgeting, forecasting, performance management, and the financial narrative delivered to the CFO, the President, executive leadership, and the Board and its committees. Beyond producing the numbers, the AVP synthesizes them — framing the strategic question, identifying the “so what,” and equipping leadership to make better decisions. The ability to look at a slide and tell the audience exactly what the data means within thirty seconds is a defining characteristic of success in this role.

Please note – although this job description refers to AVP, the title will be adjusted, accordingly, in line with the candidate’s experience.

What You’ll Do

• Lead enterprise FP&A. Own the annual budgeting and quarterly reforecasting processes end‑to‑end — setting the calendar, framework, and standards; partnering with business‑unit leaders to build credible plans; and presenting consolidated results and forward outlook to leadership and the Board.
• Tell the story behind the numbers. Develop narrative‑driven analysis that connects data to business performance and strategic implications. Drive a culture within the FP&A team that prioritizes insight and judgment over data presentation alone.
• Apply investment‑grade rigor. Evaluate strategic initiatives, capital deployment, new business lines, and portfolio investments using return‑on‑capital, IRR, NPV, sensitivity, and scenario analyses. Serve as an internal investment‑underwriting resource for the CFO and executive leadership.
• Own Board and committee reporting. Design the narrative arc, produce the underlying analysis, build executive‑ready materials, and prepare leadership for quarterly Board and committee discussions. Continuously raise the standard for how the Company communicates with its directors.
• Run fiscal management and performance. Design and maintain the Company’s contingent liquidity framework and macroeconomic stress tests; evaluate the treasury and investment portfolio; and produce performance‑vs‑plan analyses that link financial outcomes to executive incentive metrics.
• Modernize the analytics stack. Establish core financial KPIs, dashboards, and management scorecards. Actively identify and operationalize AI use cases that improve the speed, quality, and depth of financial analysis across the team.

What You Bring

Required

• Bachelor’s degree in Accounting or Finance; MBA or Master’s in a related field preferred.
• Minimum 5 years of progressive experience in FP&A or a corporate finance function, with a demonstrated track record building and communicating financial plans and analyses to executive‑level audiences.
• Hands‑on ownership of an enterprise budgeting and forecasting cycle, including direct partnership with business‑unit leaders and presentation of consolidated results to executive leadership or a Board.
• Demonstrated, hands‑on experience applying AI tools to finance and analytical work — including LLMs, AI‑enabled analytics platforms, agentic workflows, and the automation of repetitive reporting or modeling tasks.
• Proficiency with at least one enterprise business‑intelligence or data‑visualization platform (e.g., Power BI, Tableau, Looker, Qlik, Sigma); able to design dashboards that communicate insight, not just display data.
• Expert‑level financial modeling skills, including the ability to build, audit, and stress‑test multi‑driver operating, valuation, and capital‑allocation models.
• Exceptional written and verbal communication. Slides, memos, and briefings should be self‑evident in their conclusion.

Strongly Preferred

• Prior experience in private equity, investment banking, equity research, or a comparable investment‑management environment. Candidates without that background must demonstrate equivalent analytical rigor through investment‑quality modeling, returns‑on‑capital evaluation, or M&A and strategic‑transaction underwriting.
• Prior experience preparing materials for, and presenting to, a Board of Directors or its committees on a recurring (quarterly or more frequent) basis.
• Demonstrated ability to coach and elevate an FP&A team — building commentary, insight, and executive presence alongside technical craft.

Why This Role

This is a high‑visibility seat at a diversified Hawaiʻi investment management company. You will partner directly with the CFO and President, present to the Board, and shape how the organization deploys capital across real estate, private equity, technology, and insurance. We are not looking for someone to maintain the function as it is — we are looking for someone to raise its ceiling.