Enterprise Account Executive

Insightful; New York (NY); On-site; USD 120,000 - 130,000; Full time

Job summary

Insightful is seeking an Enterprise Account Executive to join our New York, NY team. You will drive strategic enterprise deals, building 30% to 40% of your pipeline through outbound efforts while the inbound channel generally accounts for 60% to 70%.

Additionally, you will assess customer needs, plan sales activities to hit monthly and quarterly targets, and operate with a CEO-level mindset over your book of business.

Qualifications

• 4+ years of enterprise sales experience with 1000 to 5000+ employees.
• Proven track record of closing six-figure enterprise deals.
• Experience using AI to support sales motion.
• Strong negotiation and presentation skills.
• Bachelor's degree in Business Administration, Sales or related field.
• Familiar with MEDDPICC or SPICED frameworks.
• Ability to map accounts and stakeholders.

Responsibilities

• Identify potential clients within the ICP.
• Execute outbound strategy and contribute insights to its development.
• Collaborate with Marketing on ABM motions for target accounts.
• Maintain an accurate sales pipeline and forecast monthly/quarterly.
• Proactively manage key customers during trials/POCs.
• Build multi-threaded relationships across HR, Finance, Operations and other stakeholders.
• Manage sales cycles: meetings, presentations, business case development.
• Grow accounts by expanding licenses within defined timeframes.

Skills

AI Native Seller

Enterprise sales

Six-figure deals

Negotiation

Account mapping

MEDDPICC or SPICED

Stakeholder management

Pipeline management

Education

Bachelor's Degree in Business Administration or related field

Tools

MEDDPICC

SPICED

Job description

Insightful is a leading workforce analytics platform transforming how modern companies work. We empower organizations to make confident, data-driven decisions — without ever sacrificing transparency or performance. From capacity planning and workforce analytics to cutting-edge AI adoption and business intelligence, Insightful delivers the insights leaders need to unlock productivity, optimize how work gets done, and build high-performing teams and organizations.

Our platform is purpose-built for the teams that keep businesses running — support, administration, finance, claims processing, and many more. With sophisticated, real-time reporting tailored to each team's workflow, Insightful gives every corner of the organization the visibility it needs to operate at its best.

Job Description:

Insightful is seeking an Enterprise Account Executive to join our dynamic New York, NY team. As an Enterprise Account Executive, you are a nimble sales professional who thinks outside the box but is highly strategic in your day-to-day. You will be expected to build 30% to 40% of your pipeline through an outbound motion, while the inbound channel will generally drive 60% to 70%.

Additionally, you will be in charge of assessing the needs of our key customers to offer relevant solutions and planning sales activities to achieve monthly and quarterly targets. Self-motivation and a results-driven mindset are a must. Mindset of operating your business as if you were the CEO of your own book of business.

Responsibilities:

• Identify potential clients and prospects within the insightful ICP
• Execute an outbound outreach strategy and contribute to its development with your own insights and suggestions
• Closely partner with and align with our Marketing team with our ABM motion on target accounts
• Maintain an accurate sales pipeline and forecast on a monthly and quarterly basis
• Proactively manage key customers’ business needs while they are in trial/POC period
• Build multi-threaded relationships across HR, Finance, Operations and various other stakeholders within your opportunities and target accounts.
• Manage sales cycles - handling meetings, presentations, business case development, etc
• Make sure the clients are satisfied with the software and explore the potential to provide them with more licenses (growth) within a defined timeframe.

Requirements:

• AI Native Seller - you know how to leverage AI to support your sales motion and day to day.
• 4+ years of proven Enterprise Experience - 1000 to 5000+ Employees
• History of consistently closing six-figure complex enterprise deals
• Excellent verbal, negotiation, and presentation skills
• Bachelor’s Degree, ideally in Business Administration, Sales, or a relevant field
• Proficiency in MEDDPICC or SPICED, with a track record of applying these frameworks to compress sales cycles and improve forecast accuracy.
• Familiar with building business cases and account stakeholder mapping.

Compensation:

The salary range for this role is $120,000 - $130,000 + uncapped commission potential.