Enterprise Account Executive

This is a fully remote position, open to applicants in New York.

📋 Description

• Take ownership of the complete sales cycle for new enterprise clients, starting from the initial conversation through to discovery, solution development, negotiation, and closing.

• Develop and oversee a sales pipeline utilizing inbound leads, SDR-generated prospects, and proactive outbound initiatives.

• Secure new business with a minimum annual contract value of $100K using Pencil’s SaaS platform, creative services, and AI-enhanced solutions.

• Engage with senior stakeholders across marketing, procurement, IT, and legal departments.

• Manage complex deals by creating multiple threads and fostering consensus within large, matrixed organizations.

• Provide customized demonstrations, capability sessions, and commercial proposals.

• Navigate through enterprise procurement processes, security assessments, and legal reviews.

• Maintain discipline in CRM usage and monitor the health of the sales pipeline.

• Internally report on opportunity progress.

• Propel enterprise growth in the US and convert pipeline opportunities into revenue.

• Measure success through new enterprise ARR, closing rate, average contract value, sales cycle duration, and forecast precision.

⛳️ Requirements

• A minimum of 5 years of experience in enterprise SaaS sales, preferably within marketing technology, creative technology, or AI-driven products.

• A demonstrated history of successfully closing new business deals ranging from $100K to $500K.

• Experience in acquiring new logos rather than simply expanding existing accounts.

• A consultative, discovery-focused sales approach.

• Strong knowledge of SaaS business models, renewal processes, and multi-stakeholder enterprise sales cycles.

• Proficiency in a contemporary enterprise sales methodology such as MEDDPICC or Challenger.

• Exceptional communication and presentation skills, particularly when addressing C-level stakeholders.

• Strong negotiation skills.

• Proficient in CRM tools like Salesforce as well as modern prospecting technologies.

• A genuine interest in AI and its evolving models.

• Legal authorization to work and reside in the designated country of employment.

🏝️ Benefits

• 25 days of paid time off (PTO) in addition to public holidays.

• Remote-first work environment, with access to offices in New York or the flexibility to work from anywhere in your home country.

• Health insurance and private medical coverage.

• Monthly stipend for wellness, fitness, and professional development.

• Enhanced parental leave policies applicable for birth, adoption, or surrogacy.

• Uncapped commission structure.