Head Bookkeeper Jobs in Boca Raton, FL (NOW HIRING)

Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk, build a clear housing plan, and drive the work forward through placement and stabilization.

Upside owns the entire housing process from start to finish. Our team engages members, coordinates with local providers and community resources, manages logistics and documentation, and stays involved until the issue is resolved. Our approach is human-first and outcome-driven, measured by real results like stable housing, completed moves, safer living environments, and successful transitions.

About the Opportunity:

Upside is hiring a Vice President of Finance to build and lead the company’s finance function as we scale across health plans, government payers, and employer groups. This role will bring greater financial rigor, accountability, and strategic insight to the business while building the systems and processes needed to support continued growth.

The VP of Finance will partner closely with the executive team to strengthen financial planning, reporting, and decision-making across the business. This leader will build the processes, models, and operating discipline needed to connect customer growth, revenue performance, and operational execution while helping shape the long-term structure of the Finance function.

This role reports to the Chief Operating Officer.

Work Location and Schedule:

Full-time, hybrid in Fort Lauderdale

Candidates based in South Florida

Must be available for travel as needed for leadership meetings, board meetings, fundraising, and other strategic business needs

What You’ll Do:

Own financial planning, budgeting, forecasting, and long-range modeling across the business

Serve as a strategic thought partner to the executive team on growth planning, investment decisions, risk management, and capital allocation

Build internal processes to track financial performance, establish accountability, and ensure leaders understand how their teams are performing against plan

Develop financial models that evaluate revenue, margins, cash flow, customer profitability, and the ROI of new initiatives

Partner with Sales and Customer Success during the contracting process to evaluate pricing, contract economics, billing requirements, and financial risk

Assess the financial and operational performance of health plan contracts, customer portfolios, and lines of business

Build scalable processes for customer invoicing, revenue recognition, accounts receivable, collections, and cash flow management

Strengthen revenue cycle operations, including billing readiness, claims, reimbursement, denials, payer requirements, and month-end reconciliation

Oversee accounting operations and external partners responsible for bookkeeping, tax, audit, and financial reporting

Ensure accurate monthly closes, financial statements, reconciliations, GAAP compliance, and audit readiness

Establish internal controls, financial policies, reporting standards, and systems that support continued growth

Prepare financial reporting, forecasts, and materials for executive leadership, the board, and investors

Support fundraising, financial due diligence, investor relations, and potential M&A or acquisition activity

Build the internal Finance team over time and determine the appropriate long-term structure across Finance, Accounting, FP&A, and Revenue Cycle

Partner with Technology, Data, and Operations to improve financial reporting, data integrity, and automation

What We’re Looking For:

10+ years of progressive experience across strategic finance, FP&A, accounting, or related finance functions

Experience serving as a VP of Finance, Head of Finance, Controller, or senior finance leader in a scaling organization

Strong healthcare finance experience, ideally within digital health, payer services, managed care, value-based care, or healthcare technology

Hands‑on understanding of revenue cycle management, including billing, claims, reimbursement, payer contracts, and collections

Experience building financial models, forecasts, budgets, and performance reporting from the ground up

Ability to understand complex customer contracts and translate them into billing processes, financial forecasts, and operational requirements

Experience partnering with Sales and executive teams on pricing, contract economics, and growth decisions

Strong knowledge of GAAP, financial statements, monthly close, audit readiness, and internal controls

Experience overseeing outsourced accounting teams, external advisors, or other financial partners

Experience preparing financial materials for boards, investors, and executive leadership

Exposure to fundraising, due diligence, M&A, or acquisition processes

Strong business judgment and the ability to balance financial discipline with growth opportunities

Ability to translate financial insights into clear operational actions and accountability across teams

Comfort operating in a fast-paced environment where processes, systems, and team structures are still being built

Experience with ERP, accounting, financial planning, and data visualization tools

Compensation and Benefits:

Salary Range: 180k - 215k

Meaningful equity

Medical, dental, and vision coverage