Director of Finance And Operations

Director of Finance & Operations Confidential Search by Executive Career Upgrades Fort Lauderdale, FL | On-site, Monday–Friday You know how to bring structure to a busy business, get a team working toward the same priorities, and understand what the numbers are telling you. Now imagine putting those strengths to work with direct access to the founder and the authority to turn your recommendations into action. Executive Career Upgrades is conducting a confidential search for a Director of Finance & Operations on behalf of an established business in the health insurance sector. In this role, you will lead a five-person team and take charge of daily operations, team accountability, and practical financial oversight. The scope is broad, the work is hands-on, and your contribution will be visible throughout the business. This is an opportunity to become the leader the founder relies on to keep the business moving and make it work better. Why This Role Deserves Your Attention · Room to make decisions. Take ownership of daily operations with authority to solve problems within approved budgets and your delegated scope. · A direct relationship with the founder. Share your ideas, influence priorities, and help turn business goals into execution. · A team you can develop. Coach five employees, build accountability, and help people do their best work. · Results you can see. Watch your decisions translate into smoother workflows, better financial visibility, and stronger follow-through. · An opportunity to use your full range of skills. Combine people leadership, business operations, and financial judgment in one role. You will be the dependable on-site leader who sets direction, removes obstacles, and makes sure commitments turn into completed work. · Lead employees across finance, customer service, and administrative functions. · Set clear expectations for priorities, deadlines, work quality, attendance, and accountability. · Coach employees, recognize progress, and address performance concerns promptly. · Coordinate workloads, staffing coverage, and handoffs so important details do not get lost. · Handle routine hiring, onboarding, and employee transitions within approved authority. · Make day-to-day decisions confidently, involving the founder in significant personnel matters and decisions outside your scope. Understand the Numbers and Drive Action You do not need to be a career finance professional. You do need to understand how money moves through a business and recognize when something needs attention. · Read and interpret profit and loss statements, balance sheets, and cash flow reports. · Analyze revenue, expenses, and trends to identify concerns and opportunities for improvement. · Monitor cash needs, receivables, payables, and upcoming obligations with bookkeeping and accounting resources. · Support budgeting and track expenses against approved plans. · Investigate discrepancies, ask useful questions, and recommend practical next steps. · Maintain clear purchasing, payment, and expense approval procedures. Make the Business Run Better · Improve workflows that cause delays, errors, or unnecessary work. · Keep a practical scorecard of team performance, service issues, open priorities, and key financial measures. · Give the founder clear updates, actionable recommendations, and dependable follow-through. · Keep procedures, business systems, and employee access organized. · Work with outside technology specialists to introduce approved tools and automation that save time and improve execution. What Will Help You Succeed You are comfortable taking responsibility. When something needs attention, you investigate, make a thoughtful decision, and follow through. You can have a direct performance conversation, explain a financial concern in plain language, and keep the team focused when priorities compete. You bring: · 3+ years of leadership experience directly managing teams, including coaching and performance accountability. · The ability to interpret a P&L, analyze revenue and expenses, understand cash flow, and use that information to guide decisions. · Experience setting priorities, solving operational problems, and keeping work on track. · Strong spreadsheet skills and comfort with financial reporting software and business systems. · Clear communication, sound judgment, and discretion with sensitive information. · Availability to work on-site in Fort Lauderdale, Monday–Friday. Experience in insurance or financial services is a plus. A background in small-business operations, working directly with a founder, or coordinating process improvements would also be valuable. Practical financial knowledge and proven team leadership are essential. Compensation · First 90 days: $90,000–$115,000 annualized base salary. · After 90 days: Anticipated increase to approximately $125,000–$140,000 annualized base salary. If you are energized by the opportunity to lead a team, make meaningful decisions, and take responsibility for how a business performs, we want to hear from you.