Senior Enterprise AI Ad Sales Executive

Pencil; New York (NY); Hybrid; USD 150,000 - 250,000; Full time

Benefits offered by this job

25 days PTO plus public holidays

Remote-first, with New York office if/

Health insurance / private medical

Monthly stipend for wellness, fitness,

Enhanced parental leave policies

Job summary

Pencil in New York is seeking an Enterprise Account Executive with real enthusiasm for AI to own the full sales cycle for net-new enterprise clients in the US, closing deals starting at $100K in annual contract value and guiding prospects from discovery to close with senior stakeholders.

You’ll build pipelines with inbound and outbound efforts, navigate procurement, security and legal reviews, and deliver tailored demos and proposals to marketing, IT and procurement teams.

Qualifications

• 5+ years in enterprise SaaS sales, ideally in marketing tech, creative tech or AI-driven products.
• A proven track record of closing net-new business at $100K to $500K.
• A consultative approach: you run discovery-led cycles, uncover real business pain and tailor proposals that drive measurable outcomes.
• A strong understanding of SaaS business models, renewal dynamics and multi-stakeholder enterprise sales cycles.
• Fluency in a modern enterprise sales methodology (MEDDPICC, Challenger or similar).
• Excellent communication: confident presenting to C-level, influencing across complex organizations and writing clear, persuasive proposals.
• Skilled negotiation that balances commercial goals with long-term relationship value.
• Proficiency with CRM software (like Salesforce) and modern prospecting tools.

Responsibilities

• Own the full sales cycle for net-new enterprise clients in your territory from first conversation through discovery, solution shaping, negotiation and close.
• Build and manage your own pipeline, combining inbound and SDR-sourced opportunities with proactive outbound into target accounts within our Ideal Customer Profile.
• Close new business starting at $100K in annual contract value, combining Pencil’s SaaS platform with creative services and AI-driven solutions.
• Engage senior stakeholders across marketing, procurement, IT and legal, multi-threading complex deals and building consensus in large, matrixed organizations.
• Deliver tailored demos, capability sessions and commercial proposals adapted to each prospect’s sector, business model and creative operating setup.
• Navigate enterprise procurement, security and legal review as a standard part of every deal at this level.
• Maintain CRM discipline, forecasting pipeline health internally and reporting on opportunity progress.

Skills

Enterprise SaaS sales

Closing net-new business

Consultative selling

SaaS business models

MEDDPICC / Challenger

Strong communication

Negotiation

CRM proficiency

Tools

Salesforce

Prospecting tools

Job description

Pencil in New York is seeking an Enterprise Account Executive with real enthusiasm for AI to own the full sales cycle for net-new enterprise clients in the US, closing deals starting at $100K in annual contract value and guiding prospects from discovery to close with senior stakeholders.

You’ll build pipelines with inbound and outbound efforts, navigate procurement, security and legal reviews, and deliver tailored demos and proposals to marketing, IT and procurement teams.