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 account-based marketing

What Success Looks Like Year One Targets

Revenue: Close new annual recurring revenue across ContractSage and Policy Sage

Pipeline: Build and maintain 3x pipeline coverage with a healthy mix of single-product and dual-product opportunities

Product Mix: Achieve balanced performance across both platforms, with 30%+ of closed deals involving cross-sell or multi-product adoption

Customer Expansion: Identify and close at least 3 upsell or expansion opportunities within your existing customer base

Market Intelligence: Become a go-to resource for product and marketing teams, providing insights on competitor positioning, customer needs, and market trends

Why Join Contract Sage Inc.

Qualified leads delivered to you. Unlike typical sales roles where you're constantly hunting, our marketing team generates a steady flow of inbound leads from companies actively seeking compliance solutions. You'll spend more time selling and less time prospecting.

Uncapped earning potential. Your success directly impacts your compensation. Top performers earn $200K+ with our commission structure. We reward those who can efficiently qualify, nurture, and close the opportunities we provide.

Two explosive markets. You're selling into contract management (a $2.9B market growing 13% annually) and GovTech/policy intelligence (a $600M market growing 22% annually). Both are ripe with opportunity as AI adoption accelerates and compliance requirements intensify.

Broad market appeal. Every B2B company with compliance obligations is a potential customer. From startups to Fortune 500s, across every industry—if they manage contracts or track legislation, they need our solutions.

First-mover advantage. While competitors focus on one vertical, you're uniquely positioned to offer enterprises comprehensive compliance intelligence for both contracts and legislation. This is your chance to define a category.

Real impact. You're not selling widgets. You're helping compliance teams prevent costly violations, helping legal teams avoid contract disasters, and helping government affairs professionals stay ahead of legislative risk. Your work matters.

Autonomy and support. We provide the leads, tools, and training. You bring the drive and closing ability. No micromanagement—just clear expectations, solid support, and the freedom to work your deals your way.

Learn cutting-edge AI. You'll become an expert in how AI is transforming legal, compliance, and government affairs functions. This expertise will serve your career for decades as AI becomes central to every business.

Collaborative culture. Work alongside founders who are invested in your success and a team that celebrates wins together. We're building something special, and we want people who are energized by that mission.

Our Sales Process & Tools

You'll work with a modern, efficient sales stack designed to let you focus on selling, not admin. Plus, you'll receive consistent lead flow from our marketing engine—inbound prospects who've already expressed interest in solving their compliance challenges.

Lead Sources You'll Receive:

• Inbound demo requests from website visitors
• Content download leads (whitepapers, ROI calculators, compliance guides)
• Webinar attendees interested in AI compliance solutions
• Trade show and conference leads from industry events
• Referrals from existing customers

Your Sales Stack:

• CRM: Salesforce for pipeline management and lead tracking
• Outreach: Automated sequences and cadences for lead nurturing
• Demo Environment: Fully functional platforms to run live analyses
• Content Library: Battle-tested pitch decks, ROI calculators, case studies, and objection-handling frameworks
• Enablement: Ongoing training on AI capabilities, industry trends, competitive positioning, and lead qualification best practices

How to Apply

We're looking for salespeople who get excited by complexity, thrive in consultative environments, and love being the smartest person in the room about how AI is transforming business intelligence.

To apply, send your resume and a brief cover letter answering these three questions:

• Describe your experience working with qualified inbound leads. How do you prioritize and convert marketing-generated opportunities into closed deals?
• Tell us about selling to compliance-focused buyers (Legal, Government Affairs, Compliance, Risk Management, Procurement). What's your approach to understanding their unique pain points?
• Why are you excited about selling AI-powered compliance solutions across both contracts AND legislative intelligence? What opportunity do you see in helping B2B companies manage compliance risk?

Equal Opportunity Employer

Contract Sage Inc. is committed to creating a diverse and inclusive workplace. We are an equal opportunity employer and do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected characteristic. We believe diverse teams build better products and serve customers better.

Contract Sage Inc. – Clear insight. Confident action.

Pay: $101,134.85 - $121,796.80 per year

Work Location: Remote