Enterprise AI Solutions Executive

About Contract Sage Inc.

Contract Sage Inc. is revolutionizing how organizations harness intelligence from their most critical business documents. We've built two game-changing AI platforms that turn complexity into competitive advantage:

ContractSage – Enterprise contract intelligence that analyzes thousands of contracts in seconds, surfacing risks, obligations, and opportunities that drive strategic decisions. Trusted by Fortune 500 companies, PE firms, and fast-growing businesses managing complex agreements.

Policy Sage – AI-powered legislative intelligence that monitors 10,000+ bills daily across all 50 states and Congress, giving government affairs, compliance, and advocacy teams the foresight to act before competitors even know what's coming.

We're not just another SaaS company. We're empowering executives to make million-dollar decisions with confidence, helping legal teams work at the speed of business, and giving policy professionals the strategic edge they need to shape outcomes rather than react to them.

The Opportunity

We're seeking a high-performing Enterprise AI Solutions Executive who thrives on converting opportunity into revenue. This isn't a typical sales role where you're cold-calling all day. You'll receive qualified inbound leads from our active marketing campaigns—companies already interested in solving their compliance challenges with AI.

What makes this role unique: You'll work with compliance-focused decision-makers across any B2B industry—Legal teams managing contract obligations, Government Affairs professionals tracking legislative risk, Compliance Officers monitoring regulatory changes, and Procurement teams ensuring vendor adherence. Whether it's a manufacturing company worried about supplier contract compliance or a healthcare system tracking policy changes, if they have compliance needs around contracts or legislation, they're your prospect.

The best part? You're not starting from scratch. Our marketing engine generates consistent lead flow, giving you a running start. Your success comes from your ability to qualify these leads, run compelling discovery, demonstrate value, and close deals efficiently while also building additional pipeline through your own strategic outreach.

What You'll DoStrategic Selling Across Two Platforms

Master both solutions deeply. Understand ContractSage's contract intelligence capabilities and Policy Sage's legislative tracking power inside and out. Know when each solves specific pain points and when the combination creates exponential value.

Identify cross-sell and upsell opportunities. Recognize when a client using ContractSage for vendor agreements would benefit from Policy Sage to track procurement regulations. Spot when a Policy Sage customer's legislative alerts reveal contract implications.

Build multi-threaded relationships. Navigate complex enterprise organizations where your champion in Legal needs contract intelligence while their colleagues in Government Affairs need legislative intelligence. Orchestrate introductions and create internal momentum across departments.

Drive Revenue Growth

Convert qualified leads into closed deals. You'll receive a steady stream of inbound leads from our marketing efforts—companies actively seeking compliance solutions for contracts and legislative tracking. Your job is to qualify, nurture, and close these opportunities efficiently.

Own your pipeline. Manage the full sales cycle from initial contact to close for both ContractSage and Policy Sage, with deal sizes ranging from $30K to $250K+ annually. Balance company-provided leads with your own prospecting to maximize revenue.

Execute strategic outreach. Target any B2B company with compliance needs—from manufacturing and healthcare to technology, financial services, and professional services firms. If they have contracts to manage or legislation to track, they're a prospect.

Focus on compliance decision-makers. Reach legal teams managing contract compliance, government affairs professionals tracking legislative risk, compliance officers monitoring regulatory changes, and procurement teams ensuring vendor contract adherence.

Demonstrate ROI with precision. Use financial modeling and business case development to show prospects exactly how AI-powered contract and policy intelligence will save them time, reduce risk, and create competitive advantage. Speak their language whether they're a General Counsel, Compliance Officer, or Director of Government Affairs.

Close complex deals. Navigate procurement processes, negotiate terms, handle objections, and drive consensus among multiple stakeholders to secure enterprise commitments.

Become a Trusted Advisor

Diagnose before you prescribe. Conduct discovery calls that uncover the real compliance challenges—not just surface-level pain points. Understand whether prospects are facing contract compliance risks, legislative tracking gaps, regulatory pressure, or a combination of these issues.

Educate and consult. Many prospects don't yet understand how AI can transform compliance workflows for both contracts and legislation. You'll be part educator, part consultant, helping them envision what's possible when they have instant intelligence at their fingertips.

Create "aha moments." Run compelling demos and live analyses using prospects' actual contracts or legislative concerns. Show them the power of seeing 100 contracts analyzed in minutes or catching critical bills 3 weeks before competitors.

Champion customer success. Your job doesn't end at signature. Partner with implementation and customer success teams to ensure smooth onboarding and identify expansion opportunities as clients see results.

What You BringRequired Experience & Skills

5+ years of B2B SaaS sales experience with a track record of consistently exceeding quota ($500K+ annually). Experience selling to enterprise and mid-market accounts.

Consultative selling mastery. You know how to run discovery, uncover complex business problems, and position solutions that align with strategic objectives—not just tactical needs.

Multi-product or multi-solution experience. Ideally you've sold complementary products or managed complex solution portfolios. You're comfortable with "land and expand" strategies and cross-selling within accounts.

Executive presence and communication. You can confidently present to C-level executives and translate technical AI capabilities into business outcomes. You're equally comfortable with a General Counsel, CFO, or VP of Government Affairs.

Deal orchestration skills. Experience navigating enterprise sales cycles with multiple stakeholders, procurement processes, and legal reviews. You know how to build consensus and manage competing priorities.

Self-starter mentality with strong follow-through. This is a remote role requiring strong self-discipline, time management, and the ability to thrive with autonomy. While we provide qualified leads and marketing support, you'll need to drive those opportunities to close and continuously build your own pipeline.

Highly Valued (But Not Required)

• Experience selling AI, ML, or data analytics solutions
• Background in legal tech, GovTech, contract management (CLM), or policy/compliance software
• Understanding of legal, procurement, government affairs, or regulatory compliance workflows
• Prior success in high-growth startups or scale-up environments
• Experience with Salesforce, Outreach, or similar sales tech stacks
• Hunter mentality with experience in outbound prospecting and