In-House: VP & Assistant General Counsel – Enterprise SaaS​/Sales Contracts

Our client, a leading software company serving the insurance industry, is actively seeking an attorney with strong enterprise-level SaaS agreements experience to join its legal team in Chicago as Vice President & Assistant General Counsel. The person in this position will report to the General Counsel, and will serve as the primary legal partner to the sales organization, supporting large, high-visibility transactions with global insurance carriers and major brokerage clients.

Chicago-based candidates strongly preferred, with a hybrid schedule. Flexibility may be considered for exceptional candidates located near company offices in Dallas or Atlanta.

• High-profile business-facing role, central to company growth
• Direct partnership and exposure to senior leadership
• Strong work-life balance with a collaborative, business-oriented legal team
• Competitive compensation, bonus, and equity participation

• Lead legal support for enterprise-level SaaS sales agreements and strategic customer relationships
• Draft, review, and negotiate complex B2B SaaS agreements, including MSAs, professional services agreements, data processing agreements, and strategic partnerships
• Serve as a trusted legal advisor to sales leadership, helping streamline processes and reduce unnecessary deal friction
• Identify opportunities to improve templates, workflows, and contracting strategy
• Support broader legal initiatives, including AI-related contracting and privacy
• Manage disputes and related matters as needed

• 5-8+ years of experience with enterprise SaaS sales contracts (sales-side experience required; vendor-side only profiles will not be a fit)
• Prior experience at a law firm (technology transactions preferred) and/or enterprise software company
• Experience negotiating complex, high-value B2B agreements with sophisticated customers
• Exposure to insurance, fintech, or regulated industries a plus

Chicago, IL (Hybrid: 2-3 days per week in-office)

The anticipated base salary for this position is $225,000.

(Additional compensation will include a target bonus and equity participation).

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