Director of Finance

About the Role

Rocket Lawyer is seeking a Director of Finance to lead corporate planning and forecasting, drive unit economic analysis across our AI-native solutions and attorney marketplace, and deliver strategic financial guidance to executive stakeholders to ensure enterprise-level decision support.

Reporting directly to the VP of Finance & Accounting, you will lead a high-performing finance organization, elevating cross-functional business partnership and driving continuous value creation across the enterprise.

What You’ll Do

Strategic Finance Business Partner

• Act as strategic finance partner to executive leaders across Product, Engineering, Sales, Marketing, and Operations, gaining comprehensive understanding of operational models and KPIs
• Construct dynamic forecast models and align cross-functional priorities through iterative scenario analysis, evaluating trade-offs to optimize organizational resource allocation
• Identify key operational trends, growth opportunities, and financial risks through advanced quantitative analysis, serving as a proactive advisor to the business
• Synthesize complex financial metrics into concise actionable narratives to key stakeholders

Unit Economics on Acquisition, Marketplace, and AI

• Provide active financial leadership and guidance on customer acquisition initiatives spanning paid marketing channels and an evolving partnership strategy
• Generate insights on the unit economics of the attorney marketplace, including attach rate, attorney-side economics, customer acquisition cost, cohort retention, and lifetime value to drive optimization.
• Model and monitor AI cost of sales, incorporating inference and compute consumption as key variable drivers; collaborate with leadership to optimize cost-to-serve metrics and refine unit pricing strategies

Planning and Forecasting

• Direct and oversee continuous corporate forecasting models, integrating operational metrics to evaluate top-line growth, expense trends, and projected cash flow
• Develop dynamic proforma sensitivity analyses to evaluate inherent trade-offs and guide critical business decisions
• Lead routine operating reviews alongside functional leaders, presenting budget-to-actual variances, core performance indicators, and forward-looking opportunities and risk
• Architect and manage multi-year financial projections capturing our business transformation, balancing legacy subscription income with AI-native products and marketplace revenue streams

Team Leadership & Development

• Manage, coach, and cultivate a four-person team of corporate financial analysts
• Assess and implement cutting-edge AI tools and quantitative frameworks to elevate department output and forecasting sophistication
• Foster a high-performing culture centered on collaborative business partnership, rigorous inquiry, and proactive execution

What We’re Looking For

• At least 9 to 12+ years demonstrating continuous growth in corporate finance leadership
• Mastery in quantitative modeling, capable of building complex forecasting from the ground-up and conducting proforma sensitivity evaluations
• Track record of autonomously evaluating commercial agreements, corporate integrations, and potential synergy opportunities
• Executive presence paired with exceptional financial narrative skills, adapting messaging seamlessly across cross-functional partners and senior leadership
• Adept at cross-functional consensus building, steering diverse stakeholders and aligning key priorities through persistent analytic credibility
• Background preparing board-level presentations, institutional investor decks, and lender reporting packages
• Deep expertise in Microsoft Excel, Google Workspace applications, modern AI productivity platforms, corporate analytics systems, and digital marketing performance tools
• High level of artificial intelligence literacy and practical technology integration skills

Nice to Have

• Advanced degree or professional credential such as an MBA, CPA, or CFA
• Proven success within midmarket organizations, particularly across rapidly scaling, venture-backed, or private equity-sponsored settings
• Deep domain expertise across SaaS, enterprise technology, and recurring revenue commercial frameworks
• Demonstrated exposure to two-sided marketplace dynamics or professional services business structures