Enterprise Account 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

Some of the world's biggest brands already run their advertising on our AI platform. Want to sell a platform the biggest brands already use and be rewarded BIG for every win?

At Pencil, we've built the operating system for AI-made advertising, the platform that aggregates every major AI model, so creative and marketing teams go from brief to finished asset without stitching tools together themselves. Our mission is to make AI the default in advertising without replacing creative people and we're leading that shift today: running production at scale for some of the world's biggest brands like L'Oréal, Unilever, Bayer, Diageo, and more with the legal, security, and procurement rigor enterprise clients require. We're backed by The Brandtech Group, a $4B marketing technology company that also owns Oliver and Jellyfish, giving us the scale and reach to work with the world's largest advertisers.

Open to candidates based outside New York, provided you are based within the Eastern Time Zone (ET).

What we’re looking for:

an Enterprise Account Executive with real enthusiasm for AI, to drive our enterprise growth in the US, our biggest market and one with significant opportunity still ahead of us. In this role, you’ll own the full sales cycle, from qualified opportunity through negotiation and close. You’ll work closely with our SDR team and engage senior marketing, procurement and executive stakeholders. You’ll bring net-new clients to Pencil, closing deals starting at $100K in annual contract value. The role and its sales motion are proven, and you’ll be instrumental in converting a significant share of our pipeline into revenue. Our uncapped commission structure rewards your results.

At Pencil, we believe that great work comes from great people. We foster a culture of collaboration, creativity and continuous learning, where your ideas are valued and your growth is supported. With flexible working from home arrangements, a focus on innovation and a team that celebrates wins together, Pencil is a place where you can make a real impact in a booming industry.

Key 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.

Your background

• 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. You’ve hunted and landed new logos, not just expanded existing accounts.

• 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.

You’ll Thrive Here If You…

• You're genuinely curious about AI, you follow where the models are going and you're excited to sell something that changes every few months.

• You put the client first, you'd rather build a relationship that lasts than force a deal that doesn't fit and you take pride in the experience clients have with you.

• You act like an owner, accountable for your pipeline and your results, and you run complex deals like a project manager: organized, on top of every stakeholder and next step.

• You're collaborative, you bring teams together to win and celebrate shared success.

KPIs & Success Measures

• Annual recurring revenue (ARR) from new enterprise clients

• Close rate and average contract value

• Sales cycle length and forecast accuracy

Benefits:

• 25 days PTO plus public holidays

• Remote-first, with access to our 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