Enterprise IT Services Hunter — Remote (5M–10M)

Weekday AI; United States; Remote; USD 180,000 - 200,000; Full time

Job summary

Weekday AI is seeking a highly driven IT services sales leader to accelerate net-new business within the United States. The role focuses on selling managed services, application modernization, digital transformation, and consulting-led solutions to enterprise accounts.

The candidate should bring 15+ years in IT services sales, a proven multi-million-dollar closing track record, and strong executive engagement skills. This is a remote position with travel as needed.

Qualifications

• 15+ years of IT services sales experience covering application services, managed services, digital services, or consulting-led engagements.
• Minimum 5 years in a pure new-business hunter capacity selling to large enterprise customers.
• Proven track record of closing multi-million-dollar IT services deals.
• Strong consultative selling capabilities and ability to lead complex solution conversations.
• Demonstrated collaboration with presales and delivery teams for tailored solution creation.
• Excellent communication and executive relationship–building skills.
• Consistent career tenure of 3–5 years per organization.
• Previous experience in IT services organizations is mandatory.
• Must be authorized to work in the U.S. without sponsorship.
• Flexibility to travel based on business needs.

Responsibilities

• Full-Cycle IT Services Sales: Own the complete sales lifecycle—prospecting, pitching, solution alignment, negotiation, and closure for new enterprise accounts.
• Revenue Target Ownership: Deliver USD $5M–$10M in annual recognized revenue through multi-year IT services contracts.
• Executive Engagement: Build and nurture relationships with senior stakeholders, including C-level executives and functional leaders.
• Market & Account Expansion: Identify white-space opportunities and align business challenges with suitable IT services offerings.
• Solution Collaboration: Partner with delivery, presales, and solution architecture teams to craft customized solution proposals.
• Pipeline Management: Maintain a healthy sales pipeline and provide accurate forecasts.
• Industry Engagement: Represent the organization at industry events, partner forums, and digital platforms relevant to IT services.

Skills

Full-cycle IT services sales

Enterprise sales

Executive engagement

Solution selling

Pipeline management

Negotiation

Cross-functional collaboration

Travel readiness

Job description

Weekday AI is seeking a highly driven IT services sales leader to accelerate net-new business within the United States. The role focuses on selling managed services, application modernization, digital transformation, and consulting-led solutions to enterprise accounts.

The candidate should bring 15+ years in IT services sales, a proven multi-million-dollar closing track record, and strong executive engagement skills. This is a remote position with travel as needed.