Vice President of Sales

Opportunity Engine, Inc.; Illinois; On-site; USD 180,000 - 280,000; Full time

Job summary

Opportunity Engine, Inc. is seeking a proven Vice President of Sales to own the company-wide sales quota and drive sustained year-over-year revenue growth for its AI-driven legal technology platform.

As a hands-on player/coach, you will set sales strategy, personally win enterprise business with general counsel and legal operations, and build a high-performing sales organization. Startup experience and strong forecasting are essential.

Qualifications

• Proven record of sustained year-over-year revenue growth in enterprise software.
• Experience selling legal technology to corporate legal departments.
• Startup experience building and scaling sales teams, processes and pipeline.
• Direct accountability for a company-wide or business-unit sales quota.
• Strong forecasting, sales operations, executive communication and board reporting.

Responsibilities

• Own the company’s sales number and deliver against annual and quarterly targets through new customer acquisition and account expansion.
• Personally prospect, build executive relationships, and close strategic enterprise deals with general counsel, legal operations leaders, and procurement stakeholders.
• Build a repeatable sales approach, including account targeting, opportunity qualification, value-based selling, and deal execution.
• Recruit, coach, and lead sales talent while remaining actively involved in customer conversations and negotiations.
• Partner with Marketing to develop qualified pipeline and with Product and customer-facing teams to align customer needs and commercial commitments.
• Own forecasting, CRM discipline, pipeline reviews, and timely visibility into sales risks and opportunities.
• Prepare and present board reporting on sales results, quota attainment, bookings, pipeline, forecast accuracy, and progress against the growth plan.

Skills

Enterprise software

Sales leadership

Forecasting

Executive communication

Tools

CRM

Job description

A legal technology company helps corporate legal departments improve outside counsel selection, manage law firm rates, and make more informed decisions about legal spend through an AI-driven software platform. This is an opportunity to help shape company strategy and build a sales organization serving corporate legal teams.

ABOUT THE ROLE

The company is seeking a proven Vice President of Sales to own its company-wide sales quota and drive sustained year-over-year revenue growth. As a member of the leadership team, you will set sales strategy, personally win enterprise business, and build a high-performing sales organization. This hands-on player/coach opportunity calls for a leader who has scaled revenue in a startup and sold legal technology to corporate legal buyers.

• Own the company’s sales number and deliver against annual and quarterly targets through new customer acquisition and account expansion.
• Personally prospect, build executive relationships, and close strategic enterprise deals with general counsel, legal operations leaders, and procurement stakeholders.
• Build a repeatable sales approach, including account targeting, opportunity qualification, value-based selling, and deal execution.
• Recruit, coach, and lead sales talent while remaining actively involved in customer conversations and negotiations.
• Partner with Marketing to develop qualified pipeline and with Product and customer-facing teams to align customer needs and commercial commitments.
• Own forecasting, CRM discipline, pipeline reviews, and timely visibility into sales risks and opportunities.
• Prepare and present board reporting on sales results, quota attainment, bookings, pipeline, forecast accuracy, and progress against the growth plan.

QUALIFICATIONS

• A demonstrated record of sustained year-over-year revenue growth and consistent personal and team quota attainment in enterprise software.
• Direct experience selling legal technology to corporate legal departments and navigating complex enterprise buying processes.
• Startup experience building and scaling sales teams, processes, and pipeline with limited resources.
• Prior accountability for a company-wide or business-unit sales quota.
• Proven player/coach leadership, with success personally closing enterprise deals and developing sales talent.
• Strong forecasting, sales operations, executive communication, and board reporting skills.
• The ability to translate technology into a compelling business case tied to cost efficiency, transparency, and measurable customer value.
• Candidates should be prepared to share specific examples of revenue growth, quota attainment, strategic wins, and teams they have built.