Job description

About Us: 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 • Significant Outbound Sales led growth experience. PLG Experience a plus. • 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.

Requirements

Must-haves

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.
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.

Nice-to-haves

Significant Outbound Sales led growth experience. PLG Experience a plus.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

Platform: breezy
Effort: medium