Director of Finance

About Rocket Lawyer Founded in 2008, we believe everyone deserves to be legally protected. In one seamless experience that combines trusted legal AI and the right attorney for each legal matter, Rocket Lawyer members have always-on access to affordable legal guidance and services they need. To date we’ve helped over 30 million consumers and small businesses get the legal help they need and are now expanding the team in order to bring affordable legal protection to even more. 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 n