Heartline Staffing, a Strategic Talent Partner with Purple Cow Recruiting, is supporting a high-growth enterprise SaaS organization in hiring an Enterprise Account Executive – AI Platform.
This is a senior, quota-carrying enterprise sales role selling a horizontal AI platform that operationalizes AI across the business. This is not a point-solution or IT-only sale. You will sell top-down to executive business leaders, uncover funded enterprise priorities, and drive adoption across multiple business units.
This is a hard-filter role. If you do not meet the requirements listed below, this role will not be a fit.
What You Will Do:
• Own and close complex, enterprise-wide SaaS deals
• Lead executive-level discovery with C-suite and senior business stakeholders
• Drive top-down, executive-led sales cycles
• Build pipeline through disciplined prospecting, account mapping, and multi-threading
• Sell a horizontal enterprise platform with multiple use cases across departments
• Manage large, complex accounts and strategic opportunities
• Maintain accurate forecasting and pipeline discipline
• Partner with executive leadership on sales strategy and execution
• Represent the company in enterprise customer environments
Compensation & Role Details:
• Base Salary: $130,000 – $150,000
• Total Compensation at Plan: $220,000 – $240,000
• Equity: Meaningful equity participation
• Location: 100% Remote (must reside in Chicago, IL)
• Travel: Approximately 40%
• Relocation: Not offered
• Car Allowance: Yes (car rentals covered)
• Benefits: Comprehensive medical, dental, vision, and retirement benefits
• 7+ years of quota-carrying enterprise or strategic SaaS sales experience
• Proven experience selling an AI platform, workflow automation platform, or horizontal enterprise SaaS platform
• Demonstrated success selling to senior business leaders (not IT-led, not point solutions)
• Experience owning large, complex enterprise accounts (5,000+ employees or $1B+ revenue)
• Consistent quota attainment with at least 2 of the last 3 years over target
• Strong career progression with no excessive job hopping
• Currently residing in Chicago, IL with existing enterprise relationships
• Bachelor’s degree required
All requirements listed above are mandatory and non-negotiable.