VP of Sales

We are seeking a VP of Sales to lead Legal On’s sales organization in the United States. Reporting directly to the CEO, you will own new customer acquisition across a broad market—from small and midsize businesses to complex enterprise accounts.

This is an ideal role for a sales leader who thrives on being personally involved in selling while also leading and developing a team. You will lead a team of Account Executives and SDRs, engage directly with senior buyers, and establish the strategy, operating discipline, and culture required to produce consistent pipeline and win increasingly valuable and complex opportunities. You will combine hands‑on sales leadership with rigorous use of data, AI, continuous iteration, and a clear point of view about where and how Legal On can win.

What you'll do

• Sales Strategy and Revenue Leadership
• Own Legal On’s new-logo sales strategy and performance across SMB, mid-market, and enterprise customers.
• Identify and direct resources toward the most promising industries, use cases, and customer profiles.
• Build a sales organization capable of supporting both efficient lower-value transactions and sophisticated enterprise opportunities.
• Improve outbound strategy, account selection, messaging, sequencing, event follow-up, and field prospecting.
• Partner closely with Marketing on campaigns, events, content, account‑based programs, and other pipeline initiatives.
• Personally participate in conferences, executive events, prospect meetings, and other field activities that create and accelerate opportunities.
• Help the team navigate complex buying groups, security and legal reviews, product evaluations, procurement, and executive decision‑making.
• Instill strong enterprise‑selling habits, including account planning, multithreading, in‑person engagement, mutual action plans, and executive alignment.
• Develop creative commercial and sales strategies that allow the team to win while Legal On’s product and the broader AI market continue to evolve.
• Data and Operational Excellence
• Use quantitative and qualitative evidence to identify bottlenecks, test improvements, and continuously refine the sales process.
• Leverage AI to empower our people on their highest‑value activities while AI handles the rest.
• Refine a forecasting process that is accurate, transparent, and grounded in observable customer behavior.
• Partner with Sales Operations on reporting, tooling, compensation, and process.
• Balance analytical rigor with speed, experimentation, and sound judgment.
• Team Leadership and Culture
• Recruit, retain, lead, and develop a high‑performing team of Account Executives and SDRs.
• Set a high bar for preparation, customer empathy, execution, accountability, and continuous improvement.
• Create a culture in which people learn quickly, share insights openly, and take ownership of outcomes.
• Remain close enough to customers and deals to coach from direct knowledge rather than reports alone.
• Cross‑Functional Leadership
• Partner with Marketing to sharpen positioning, improve pipeline programs, and translate market insights into effective campaigns.
• Work closely with Product to communicate prospect feedback, evolving buyer needs, competitive dynamics, and emerging opportunities.
• Partner with Legal Engineering to design and deliver tailored product trials that demonstrate Legal On’s value against each prospect’s workflows, priorities, and success criteria.
• Collaborate with Customer Success to ensure strong handoffs while maintaining clear ownership of new‑logo acquisition.
• Represent the voice of the market in company planning and executive decision‑making.

Qualifications

• 8+ years of successful B2B SaaS sales experience, including substantial experience leading and growing high‑performing sales teams.
• A strong record of…