Senior Director, Strategic Finance - Flag Business

Flow • Bay Harbor Islands, FL

5d

About The Position

Flow is seeking a highly strategic, operationally focused, and technology-forward Senior Director of Strategic Finance to support our Flag Business, the company’s core Property Management platform. This role will serve as the primary finance partner to the Business Lead of Flag Business while reporting directly to the CFO. This role will operate as an embedded business partner within the Property Management organization, helping drive operational performance, profitability, scalability, and strategic growth initiatives. The ideal candidate combines strong financial acumen with operational insight, leadership presence, and a deep understanding of how AI, automation, and data analytics can transform business performance and decision-making. This position is highly visible and will play a critical role in shaping the future of Flow’s largest and most strategic operating business.

Requirements

• Bachelor's degree in Finance, Accounting, Economics, Business Analytics, or related field required; MBA and/or CPA preferred.
• 12+ years of progressive FP&A, strategic finance, or operational finance experience.
• Real estate, property management, hospitality, or multi-site operational business experience strongly preferred.
• Proven ability to partner closely with operational business leaders in a highly collaborative environment, with a solutions-oriented, entrepreneurial mindset and a bias toward action.
• Experience leveraging AI, automation, and advanced analytics tools within finance or operational decision-making processes, paired with a genuine passion for technology and continuous improvement.
• Strong financial modeling, forecasting, and analytical capabilities, with the ability to simplify complex financial concepts into clear, actionable business insights.
• Advanced Excel skills and experience with ERP, planning, BI, and visualization tools (Power BI, Tableau, SQL, etc.).
• Exceptional communication, presentation, and relationship-building skills, with strong executive presence and the ability to influence across all levels of the organization.
• Highly strategic thinker with strong operational curiosity, hands-on execution capabilities, and the adaptability to thrive in a fast-paced, growth-oriented environment.
• Strong executive presence and influencing skills
• Entrepreneurial mindset with bias toward action
• Ability to simplify complex financial concepts into actionable business insights
• Collaborative, adaptable, and solutions-oriented leadership style

Responsibilities

• Serve as the lead finance partner to the Business Lead for Flag Business (Property Management).
• Provide proactive financial and operational insights to support strategic decision-making, business growth, and operational efficiency.
• Participate in leadership meetings and act as a trusted advisor on performance management, pricing strategies, resource allocation, and profitability optimization.
• Help translate operational objectives into measurable financial outcomes and KPIs.
• Support strategic initiatives, acquisitions, market expansion, and new service offerings through rigorous financial analysis and scenario modeling.
• Lead budgeting, forecasting, long-range planning, and monthly financial reviews for the Flag Business platform.
• Develop sophisticated operational and financial models to evaluate performance drivers, labor efficiency, customer retention, occupancy trends, margin performance, and growth initiatives.
• Deliver timely variance analysis and actionable recommendations to improve business performance.
• Monitor and analyze key operating metrics across the property management portfolio.
• Drive forecasting accuracy and business visibility through dynamic planning tools and real-time analytics.
• Champion the integration of AI-enabled analytics, automation, and intelligent reporting tools across the Property Management finance function.
• Leverage predictive analytics and modern data platforms to improve forecasting, operational planning, and decision-making speed.
• Partner with Technology and Operations teams to enhance data infrastructure, automation, and business intelligence capabilities.
• Identify opportunities to streamline workflows and eliminate manual processes using AI and automation technologies.
• Help build a next-generation finance organization aligned with Flow Life’s innovation-first culture.
• Prepare executive-level dashboards, KPIs, board materials, and management reporting packages.
• Deliver clear, concise, and actionable financial insights to both finance and operational leadership teams.
• Create business performance narratives that connect operational activity to financial outcomes.
• Support lender, investor, and executive reporting requirements as needed.
• Partner closely with Accounting, Operations, Asset Management, Revenue Management, and Technology teams.
• Improve alignment between operational execution and financial planning processes.
• Drive consistency in reporting methodologies, data governance, and performance measurement standards across the business.
• Assist in evaluating organizational investments, staffing models, vendor relationships, and operational initiatives.

Benefits

• Comprehensive benefits package (Medical / Dental / Vision / Disability / Life)
• Paid time off and 13 paid holidays
• 401(k) retirement plan
• Healthcare and Dependent Care Flexible Spending Accounts (FSAs)
• Access to HSA-compatible plans
• Pre-tax commuter benefits
• Employee Assistance Program (EAP), free therapy through SpringHealth, acupuncture, and other wellness offerings

What This Job Offers

• Job Type: Full-time
• Career Level: Senior