Remote IT Services Hunter: Enterprise Sales Leader

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

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.