Enterprise Account Executive

Pencil

. Own the full sales cycle for net-new enterprise clients, from first conversation through discovery, solution shaping, negotiation and close .

Posted 11/11/2026full-timeRemote • New York • United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in enterprise SaaS sales with a focus on closing new business and managing complex sales cycles. Proficient in engaging senior stakeholders and utilizing modern sales methodologies to drive revenue growth.

Highest-signal resume keywords

Enterprise SaaS SalesClosing New BusinessConsultative Sales ApproachCRM Software ProficiencyFluency in Sales Methodology

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Cycle ManagementNegotiation SkillsPipeline ManagementForecasting Pipeline HealthUnderstanding of SaaS Business ModelsMulti-Stakeholder SalesDiscovery-Led SalesTailored DemosCommercial ProposalsTracking Sales Metrics

Soft Skills

Excellent Communication SkillsPresentation SkillsGenuine Curiosity About AI

Tools & Technologies

SalesforceModern Prospecting Tools

Industry Keywords

Enterprise ClientsMarketing TechCreative TechAI-Driven ProductsLegal ReviewProcurement ProcessesC-Level StakeholdersARR GrowthClose RateSales Cycle Length

About the role

Key responsibilities & impact

Own the full sales cycle for net-new enterprise clients, from first conversation through discovery, solution shaping, negotiation and close
Build and manage a pipeline using inbound, SDR-sourced and proactive outbound opportunities
Close new business starting at $100K in annual contract value using Pencil’s SaaS platform, creative services and AI-driven solutions
Engage senior stakeholders across marketing, procurement, IT and legal
Multi-thread complex deals and build consensus in large, matrixed organizations
Deliver tailored demos, capability sessions and commercial proposals
Navigate enterprise procurement, security and legal review
Maintain CRM discipline and forecast pipeline health
Report opportunity progress internally
Drive enterprise growth in the US and convert pipeline into revenue
Track success through new enterprise ARR, close rate, average contract value, sales cycle length and forecast accuracy

Requirements

What you’ll need

5+ years in enterprise SaaS sales, ideally in marketing tech, creative tech or AI-driven products
Proven track record of closing net-new business at $100K to $500K
Experience hunting and landing new logos, not just expanding existing accounts
Consultative, discovery-led sales approach
Strong understanding of SaaS business models, renewal dynamics and multi-stakeholder enterprise sales cycles
Fluency in a modern enterprise sales methodology such as MEDDPICC or Challenger
Excellent communication and presentation skills, including presenting to C-level stakeholders
Skilled negotiation abilities
Proficiency with CRM software such as Salesforce and modern prospecting tools
Genuine curiosity about AI and evolving AI models
Legal right to work and remain in the country of intended work location

Benefits

Comp & perks

25 days PTO plus public holidays
Remote-first, with access to offices in New York or work anywhere in your home country
Health insurance / private medical cover
Monthly stipend towards wellness, fitness, and learning and development
Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy
Uncapped commission structure