Enterprise AI SaaS Sales Exec | Remote

Pencil; United States; Remote; USD 100,000 - 500,000; Full time

Benefits offered by this job

PTO & holidays

Remote-first

Health insurance

Wellness stipend

Parental leave

Job summary

Pencil is the operating system for AI-made advertising, powering major brands in the US. You’ll own the full enterprise sales cycle, from discovery to close, targeting logos at $100K+ ARR and collaborating with SDRs, marketing, procurement, and legal.

This role offers uncapped commissions, remote-first, and flexible work arrangements, with ET-friendly time zones. You’re joining a fast-growing team shaping how AI is adopted in advertising and building lasting customer partnerships.

Qualifications

• 5+ years in enterprise SaaS sales
• Proven track record closing net-new business at $100K–$500K
• Consultative discovery-led cycles
• Strong understanding of SaaS business models and renewal dynamics
• Proficiency with CRM and modern prospecting tools
• Familiar with MEDDPICC or Challenger methodologies

Responsibilities

• Own the full sales cycle for net-new enterprise clients from discovery through negotiation and close
• Build and manage your pipeline within target accounts
• Close deals starting at $100K in annual contract value
• Engage senior stakeholders across marketing, procurement, IT and legal
• Deliver tailored demos and commercial proposals adapted to each prospect
• Navigate enterprise procurement, security and legal review
• Maintain CRM discipline and forecast pipeline health

Skills

Enterprise SaaS sales

Close 100K-500K deals

Consultative sales

SaaS business models

MEDDPICC/Challenger

Stakeholder management

Tools

Salesforce

Job description

Pencil is the operating system for AI-made advertising, powering major brands in the US. You’ll own the full enterprise sales cycle, from discovery to close, targeting logos at $100K+ ARR and collaborating with SDRs, marketing, procurement, and legal.

This role offers uncapped commissions, remote-first, and flexible work arrangements, with ET-friendly time zones. You’re joining a fast-growing team shaping how AI is adopted in advertising and building lasting customer partnerships.