Enterprise Account Executive (3 Openings)

Enterprise Account Executive

New York, New York, United States

HireNow Staffing is actively recruiting (3) seasoned, highly skilled Enterprise Account Executives to join one of our valued client partners. HireNow Staffing is acting as a direct placement partner for this enterprise sales role within a high-growth AI B2B software environment.

This role requires a true enterprise seller who is comfortable owning complex deals from initial outreach through close. The position is heavily outbound-driven and requires the ability to navigate multi-threaded sales cycles across large organizations (5,000+ employees).

The Enterprise Account Executive will operate as a key revenue driver, working closely with leadership to execute and refine the company's U.S. go-to-market motion while managing high-value opportunities.

Core Responsibilities

• Own the full enterprise sales cycle, from outbound prospecting through contract execution
• Build and manage a high-quality pipeline (approximately 70% outbound focus)
• Engage and influence multi-stakeholder buying groups, including C-suite executives and functional leaders
• Lead complex deal cycles involving long sales timelines and multiple decision-makers
• Deliver clear, compelling messaging aligned to customer pain points in recruiting and talent workflows
• Collaborate with leadership and GTM teams to execute and refine enterprise sales strategy

Required Qualifications (Non-Negotiable)

• 812 years of B2B SaaS sales experience
• Proven success closing six-figure+ enterprise deals
• Experience managing complex, multi-threaded enterprise sales cycles
• Direct experience selling AI-native products (true AI, not repositioned SaaS)
• Background working within high-growth startup environments (Series AC)
• Demonstrated ability to generate pipeline through outbound prospecting
• Strong tenure history with consistent career progression (no job hopping)

Preferred Qualifications

• Experience selling into HR, Talent Acquisition, or workforce-related functions
• Background with companies such as Harvey, Paradox, Decagon, Writer, Eightfold, Sierra, or Glean
• Experience scaling within rapid-growth startup environments
• Strong ability to manage long-cycle, high-value deals with executive stakeholders
• High level of intellectual curiosity, competitiveness, and ownership mentality

HireNow Staffing is recruiting candidates who demonstrate:

• 8+ years of enterprise B2B SaaS sales experience
• Proven track record of closing six-figure enterprise deals consistently
• Experience navigating complex buying committees and long sales cycles
• Direct exposure to AI-driven or AI-native product sales
• Background in Series AC startup environments (growth-stage experience required)
• Strong outbound capability with a self-generated pipeline mindset

Automatic Disqualification

• Job hopping with short tenures across multiple roles
• Experience limited to large enterprise companies only (no startup exposure)
• More than 20 years of total work experience (misaligned seniority)
• Selling non-technical or lightly positioned AI solutions without real AI exposure

Standout Candidates Possess:

• Experience selling true AI products (not repackaged SaaS)
• Track record of scaling with companies through Series A/B/C growth phases
• Consistent top-performer metrics and quota attainment
• Ability to operate as both a hunter and strategic deal owner

Work Location: Onsite New York, NY

Compensation: $140,000 $175,000 base OTE: $180,000 $350,000 (50/50 split, uncapped commission) + equity

HireNow Staffing Disclaimer

HireNow Staffing is acting as a direct placement partner for this role. All candidate information is handled confidentially and evaluated against defined requirements. This job description outlines the general scope of responsibilities and qualifications. Duties may evolve based on client needs and business growth. Only candidates meeting the core qualifications will be considered for interview.