VP of Sales, Founding Team

Contract Sage | AI-Powered Contract Intelligence Platform
Equity Opportunity | Remote or Hybrid | Transformational Role

THE OPPORTUNITY
Join Contract Sage at the ground floor as our VP of Sales and Founding Team Member—where you'll build the revenue engine that transforms how mid-market to Fortune 1000 companies manage millions to billions in contractual obligations. We've proven product-market fit with our first marquee client. Now we need a proven closer to turn sophisticated AI technology into systematic, repeatable revenue.

Who We Are
Contract Sage is an AI-powered contract intelligence platform that turns complex agreements into strategic insights. We help Legal, Compliance, Finance, and Procurement teams gain instant visibility into thousands of contracts—extracting key terms, obligations, risks, and renewal triggers in seconds, not days. Our mission: Turn contractual complexity into clarity, confidence, and control.

What we've built: Enterprise-grade contract intelligence that delivers 10× faster visibility and 90% lower manual review costs, with predictive alerts that prevent missed renewals, reduce risk exposure, and unlock hidden value across every agreement.

The Role: Build Our Revenue Foundation as a Founder
This isn't about joining an established sales machine—it's about building one from scratch as a true founding team member. As our VP of Sales, you'll own revenue from $1M to $10M+ ARR, translating sophisticated market segmentation into closed deals and replicable process. You'll have founder-level equity, founder-level autonomy, and founder-level impact.

You Will:
• Own and execute the entire sales cycle—from lead generation to contract signature—targeting mid-market companies ($50M+ revenue) through Fortune 1000 enterprises across Legal Operations, CFO offices, CPOs, and Real Estate/Asset Management
• Build and refine our sales playbook, pricing strategy, and go-to-market approach based on real wins and losses
• Leverage your existing enterprise relationships to accelerate pipeline development and shorten sales cycles
• Partner directly with founders on strategic positioning, competitive differentiation, and product-market evolution
• Serve as the voice of the customer—translating buyer objections, feature requests, and competitive intelligence back to product and strategy
• Eventually build and lead a high-performing sales team as we scale past $5M ARR
• Turn our first marquee win into a repeatable reference story that opens doors across enterprise accounts

Who You Are: The Proven Closer

Required Experience:
• 7+ years of B2B SaaS sales experience with proven track record of consistently exceeding quota, including experience selling to mid-market and enterprise accounts
• Direct experience selling into Legal Operations, General Counsel, CFO, CPO, or Compliance buyer personas at companies ranging from $50M to Fortune 1000
• Demonstrated success taking a SaaS product from early traction ($1M ARR) to scaled revenue ($10M+ ARR)
• Experience with complex enterprise sales cycles involving multiple stakeholders, security reviews, and procurement processes
• History of building sales processes, playbooks, and repeatable methodologies—not just executing someone else's system
• Rolodex of existing relationships with target buyers in Legal Tech, Compliance Software, Contract Lifecycle Management, or adjacent spaces

Ideal Background (Bonus Points):
• Sold AI/ML-powered solutions or other technically sophisticated products to non-technical buyers
• Experience in Legal Tech, Contract Management, Compliance Software, or GRC platforms
• Founded or been first sales hire at a successful B2B SaaS startup
• Track record of turning pilot programs into enterprise-wide deployments

Your Superpowers:
• You're a hunter, not a farmer—you thrive on building pipeline from scratch and closing complex deals
• You speak fluently to C-suite executives and translate technical value into business outcomes
• You're comfortable with ambiguity and energized by building systems where none exist
• You're metrics-driven and obsessed with pipeline velocity, conversion rates, and win/loss patterns
• You have financial runway to operate commission-only for 6-12 months while building revenue
• You're scrappy, resilient, and willing to do whatever it takes—from cold outreach to customer success—to drive revenue
• You want ownership and equity, not a paycheck—you see this as building YOUR business, not working a job
What We Offer: Founder-Level Equity and Uncapped Upside
This is a true founding team opportunity with compensation structured like a co-founder, not an employee.

Equity Package:
• 4-6% founder-level equity stake with 4-year vesting and standard 1-year cliff
• At this equity level, you're building YOUR company, not just selling someone else's product
• Potential accelerated vesting tied to revenue milestones—hit targets faster, own more sooner
Commission Structure:
• Uncapped commission starting at dollar one—you earn from the very first deal
• 15-25% commission on the first $2M ARR (well above industry standard 10%)
• Commission structure designed to reward aggressive early traction—the faster you close, the more you earn
• Transparent, founder-friendly terms—no complex clawbacks or bureaucratic approval processes

Base Salary:
• Commission-only structure (no base salary). This role is designed for entrepreneurial sellers with financial runway who want maximum equity upside and are willing to bet on themselves.

Total Compensation Potential: With 5% equity in a company scaling to $50M+ valuation and aggressive commission on early deals, your first 18 months could generate $500K-$1M+ in combined commission and equity value—if you execute.

Why Join as a Founding Team Member:
• True ground-floor opportunity with proven product-market fit and marquee customer validation
• Founder-level equity (4-6%) typically reserved for co-founders—rare for a VP-level role
• Direct partnership with founders on strategic direction, pricing, positioning, and product roadmap
• Massive addressable market—every mid-market to enterprise company with 100+ contracts is a potential customer
• Product that solves a painful, expensive problem that buyers actively seek solutions for—inbound interest is real
• Flexible remote or hybrid work environment with full autonomy over your sales approach
• Opportunity to build and eventually lead an entire sales organization as we scale past $10M ARR

How to Apply
If you have the sales DNA, financial runway, and entrepreneurial mindset to build revenue from the ground up with founder-level equity, we want to hear from you.

Send us:
• Your resume highlighting your most impressive wins and revenue milestones
• A brief note (4-6 sentences) explaining: (1) your biggest deal and how you closed it, (2) why commission-only + founder-level equity is the right fit for you right now, (3) which of our target buyer personas (Legal Ops, CFO, CPO, Real Estate) you have the strongest relationships with, and (4) your timeline to revenue—how fast can you close your first deal?
• Links to your LinkedIn profile and any relevant case studies, quota attainment records, or sales performance metrics

Contract Sage is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Ready to turn contracts into your competitive advantage? Let's build the future of contract intelligence together.