Vice President of Acquisitions & Financial Planning

Position Summary

The Vice President of Acquisitions and Financial Planning will lead Esquire Law Services' enterprise financial planning and analysis function and its acquisition program. Reporting to the Chief Executive Officer, this executive will create an integrated view of operating performance, cash, capital and growth; build and manage a disciplined acquisition pipeline; lead financial underwriting and transaction execution; and maintain accountability through post-close integration and value realization. The Vice President will serve as a central advisor to the CEO and Board of Directors and coordinate leaders, acquisition targets, lenders, legal counsel, accountants and other transaction partners.

Integrated ownership mandate: Connect enterprise forecasts and capital decisions to acquisition strategy, deal economics and integration results. Every material forecast, investment decision and transaction should have documented assumptions, clear ownership, timely executive reporting and measurable outcomes.

Core Responsibilities

1. Enterprise Financial Planning and Performance Management

• Planning framework. Lead annual budgeting, rolling forecasts and long-range planning across entities, offices, practice areas and operating functions.
• Integrated modeling. Build linked income statement, balance sheet, cash-flow and operating models that incorporate organic initiatives, acquisitions and operational changes.
• Driver-based analysis. Translate case volume, intake conversion, staffing, productivity, marketing, settlement timing, fees and other operating drivers into financial outcomes.
• Performance management. Maintain KPIs, dashboards and scorecards that make revenue, profitability, productivity, cash generation and strategic execution clear and measurable.
• Forecast discipline. Measure forecast accuracy, explain material variances and continuously improve assumptions, source data and planning methods.

2. Acquisition Strategy and Pipeline Development

• Acquisition strategy. Translate enterprise growth priorities into target profiles, market theses, investment criteria and actionable sourcing plans.
• Pipeline ownership. Build and maintain a qualified pipeline through direct outreach, referrals, advisors, industry relationships and proprietary research.
• Opportunity qualification. Assess strategic fit, ownership objectives, transaction readiness, financial profile, operating quality, cultural alignment and probability of close before resources are committed.
• Relationship management. Develop trusted relationships with owners, sellers, intermediaries and key decision-makers while protecting confidentiality and maintaining momentum.

3. Financial Underwriting and Deal Structuring

• Financial diligence. Analyze historical and projected revenue, earnings, cash flow, working capital, debt, owner adjustments, concentration, productivity and operating drivers.
• Valuation and returns. Develop valuation ranges, stand-alone and combined forecasts, and return analyses using appropriate multiples, discounted cash flow, comparable transactions and scenario-based methods.
• Deal economics. Model purchase price, financing needs, cash at close, earnouts, seller financing, rollover equity, holdbacks, working-capital adjustments, synergies, integration costs and downside protections.
• Commercial structuring. Partner with leadership and legal, tax and finance advisors to evaluate transaction structures and negotiate key business terms within approved parameters.
• Investment judgment. Identify assumptions, sensitivities, risks and value-creation levers and provide the CEO and Board with an independent, evidence-based recommendation.

4. Due Diligence, Negotiation and Closing

• Diligence leadership. Build and manage a coordinated diligence process covering financial, legal, tax, regulatory, technology, cybersecurity, human capital, benefits, facilities, insurance and operations.
• Transaction control. Maintain the data room, deal calendar, responsibility matrix, issue and decision logs, transaction budget, approval record and closing checklist.
• Advisor coordination. Direct the work of attorneys, accountants, quality-of-earnings providers, lenders, consultants and internal subject-matter experts.
• Documentation and approvals. Coordinate business input into letters of intent, term sheets, purchase agreements, disclosure schedules and ancillary agreements, and secure required CEO, Board and other approvals before commitments are made.
• Closing execution. Confirm financing, funds flow, consents, regulatory requirements, employment matters, transition services and closing conditions, then lead the final transaction cadence and post-close handoff.

5. Integration Planning and Value Realization

• Early integration. Begin planning during diligence so Day 1 priorities, communications, leadership decisions and operational dependencies are resolved before closing.
• Integration roadmap. Develop and govern a 30/60/90-day plan with owners, milestones, risks and success measures across people, finance, technology, operations, brand, facilities and compliance.
• Baseline and synergy tracking. Convert the approved investment case into measurable revenue, cost, talent, technology and operating targets and monitor actual performance against those assumptions.
• Post-close accountability. Escalate variances, drive corrective action and conduct lessons-learned reviews that strengthen future acquisitions and integration playbooks.

6. Executive Reporting and Strategic Decision Support

• Executive reporting. Prepare concise monthly and quarterly reporting for the CEO and Board of Directors that explains results, drivers, risks, opportunities and required actions.
• Board and transaction materials. Develop decision-ready financial narratives, investment summaries, scenario analyses, approval recommendations and post-close performance updates.
• Strategic alternatives. Evaluate market expansion, staffing, marketing, technology, facilities, service expansion and operating-model choices using return, payback, cash and risk measures.
• Business partnership. Work with functional leaders to turn performance gaps and strategic priorities into accountable actions, measurable outcomes and timely decisions.

7. Capital Allocation, Financing and Liquidity

• Capital allocation. Prioritize organic and acquisition investments based on strategic fit, expected return, cash requirements, timing and execution risk.
• Liquidity planning. Forecast cash availability, working-capital needs and downside liquidity under normal and stressed operating conditions.
• Capital structure. Analyze debt, equity and hybrid financing alternatives and their impact on leverage, liquidity, control, covenants and returns.
• Financing review. Evaluate financing proposals, pricing, maturities and commercial terms and clearly explain their financial and operational implications.

8. Governance, Systems and Team Leadership

• Model and data governance. Maintain documented assumptions, validation checks, version control, source ownership, audit trails and disciplined access standards for material models and transaction information.
• Systems improvement. Improve planning platforms, ERP and accounting data, business intelligence, workflow automation and governed self-service reporting.
• Process discipline. Maintain repeatable FP&A and acquisition playbooks, templates, approval thresholds, diligence standards and transaction records.
• Team leadership. Build and develop a high-performing FP&A and transaction capability with clear roles, service expectations, analytical standards, accountability and succession planning.
• Confidentiality and risk. Protect sensitive client, employee, target, seller, financial, legal, lender, shareholder and Board information and ensure unresolved material risks remain visible to decision-makers.

Performance Expectations

• Financial planning. Timely budgets and forecasts, reliable data, improved forecast accuracy and early identification of material performance or liquidity changes.
• Executive insight. Clear, decision-ready reporting and recommendations that enable timely action by the CEO and Board.
• Pipeline and execution. A qualified acquisition pipeline, disciplined stage-gate progression, complete diligence and controlled, on-time closings.
• Deal quality. Final economics, protections and financing aligned with approved investment criteria and risk-adjusted return expectations.
• Integration. Day 1 readiness, timely 30/60/90-day milestone completion and measurable progress against approved value-creation targets.
• Leadership and process. Stronger controls, scalable systems, clear accountability, reduced manual work and effective development of internal capability.

Qualifications

Required

• Experience. At least 8 years of progressive experience across FP&A, strategic finance, private equity, corporate development, investment banking, transaction advisory or a closely related field, including enterprise planning and full-cycle transaction execution.
• Private equity and M&A. Direct private equity, sponsor-backed corporate development or comparable transaction experience, with demonstrated ownership of acquisitions from sourcing or evaluation through diligence, negotiation, closing and integration.
• Financial modeling. Expert ability to build integrated financial statements, driver-based forecasts, cash-flow analyses, valuations, return models, transaction models and scenarios.
• Financial and commercial acumen. Deep understanding of profitability, working capital, liquidity, leverage, capital allocation, deal structures and the operating drivers behind business results.
• Executive communication. Demonstrated ability to create Board-ready materials, explain complex financial and transaction matters clearly, and challenge assumptions constructively.
• Leadership. Track record leading teams, advisors and cross-functional workstreams through competing priorities, sensitive information and fixed deadlines.
• Systems. Advanced Excel and financial-modeling skills plus experience with ERP or accounting systems, planning tools and business-intelligence platforms.
• Education. Bachelor's degree in finance, accounting, economics, business or a related field; equivalent directly relevant experience may be considered.

Preferred

• Advanced credentials. MBA, CPA, CFA or a comparable finance, accounting or investment credential.
• Industry context. Experience in legal services, professional services, healthcare, multi-site operations or another regulated, people-intensive business.
• Growth environment. Experience in a private equity-backed, sponsor-owned, acquisitive or investor-reporting organization.
• Technology. Experience implementing or optimizing enterprise planning software, Power BI or comparable analytics and reporting tools.

Leadership Competencies

• Enterprise judgment. Connects financial, operational and transaction decisions to strategy, risk, cash and long-term value.
• Analytical rigor. Validates data, reconciles inconsistencies, tests assumptions and separates evidence from optimism.
• Deal judgment. Knows when to advance, restructure, pause or recommend walking away from an opportunity.
• Executive presence. Communicates with confidence and discretion across leadership, owners, counterparties, lenders, advisors and the Board.
• Ownership. Drives recurring planning processes and complex transactions to completion with clear accountability and follow-through.
• Constructive challenge. Raises difficult issues early and provides practical, analytically supported alternatives.
• Integrity and discretion. Protects confidential information and maintains objectivity in high-stakes financial and transaction decisions.

Work Environment and Other Requirements

• Executive presence. This role is based in Palm Beach Gardens, Florida, with an on-site/hybrid leadership model and regular engagement with the CEO and Board of Directors.
• Travel. Frequent travel may be required for firm-office visits, target meetings, diligence, negotiations, closings and integration activities.
• Availability. The role must be responsive during critical budgeting, forecasting, Board, financing, diligence, signing, closing and integration periods, including outside normal business hours when necessary.
• Scope boundaries. The role provides financial, commercial and transaction leadership but does not independently provide legal, tax, audit, broker-dealer or investment-banking services or bind the company to a transaction without written authorization.
• Scope flexibility. Responsibilities may evolve as the organization expands, completes acquisitions and strengthens its planning, reporting and integration capabilities.

Physical Requirements

This position primarily involves sedentary office work and regular use of a computer, telephone and other office equipment. The employee must be able to communicate effectively, review detailed financial information and occasionally move materials weighing up to 15 pounds. Reasonable accommodations will be provided to qualified individuals with disabilities in accordance with applicable law.