Sales Hunter - IT Services

Weekday AI (YC W21); United States; Remote; USD 180,000 - 200,000; Full time

Job summary

Weekday AI seeks a high-velocity Sales Hunter to accelerate new business for a pure-play IT services organization. You will drive end-to-end sales from prospecting to closure, focusing on managed services, application modernization, and digital transformation engagements.

You'll engage senior stakeholders at large enterprises, craft tailored solutions with delivery and presales teams, and own a USD 5M–10M annual revenue target, traveling as needed across the United States.

Qualifications

• 15+ years of IT services sales experience.
• 5+ years in a pure new-business hunter role selling to large enterprise customers.
• Proven track record of closing multi-million-dollar IT services deals.
• Strong consultative selling and executive relationship-building skills.

Responsibilities

• Own the full sales lifecycle—from prospecting to closure for new enterprise accounts.
• Deliver USD $5M-$10M in annual revenue through multi-year IT services contracts.
• Engage with senior stakeholders, including C-level executives.
• Identify white-space opportunities and align business challenges with IT services offerings.
• Collaborate with delivery, presales, and solution architecture teams to craft proposals.
• Maintain a healthy sales pipeline and provide accurate forecasts.
• Represent the organization at industry events and partner forums.

Skills

Prospecting

Executive engagement

Solution selling

Deal closure

Account expansion

Forecasting

Communication

Presales collaboration

Sales leadership

Job description

This role is for one of our clients

This role is for one of our clients

We are looking for a highly driven and experienced Sales Hunter to accelerate new business acquisition for a pure-play IT services organization. This role focuses on driving net-new revenue through selling technology services, including managed services, application modernization, digital transformation initiatives, and consulting-led solutions. This is an end-to-end sales role that requires strong prospecting skills, executive-level engagement, solution positioning, and deal closure.

Location

Remote - Within the United States

Compensation

USD $180,000 - $200,000 base + performance incentives + benefits

Annual Sales Target

USD $5M - $10M in recognized revenue

Key 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.

Candidate Profile

• 15+ years of experience in IT services sales 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