US Hiring

Weekday AI
New York, NY

This role is for one of the Weekday's clients

Min Experience: 8 years

Location: USA

JobType: full-time

We are seeking a Senior Sales Leader to drive revenue growth and strategic expansion within the data annotation and AI solutions space across the United States. This is a high-impact leadership role focused on building enterprise relationships, closing large-scale deals, and positioning advanced AI-enabled data services to high-growth technology companies and enterprises. The ideal candidate brings deep experience in consultative B2B sales, particularly in AI, machine learning, data services, or adjacent technology sectors.

Requirements

Key Responsibilities

  • Develop and execute a strategic sales plan to drive revenue growth in AI and data annotation services
  • Identify, target, and close enterprise and mid-market clients across technology-driven industries
  • Own the complete sales cycle from prospecting to contract negotiation and deal closure
  • Build strong relationships with C-level executives, product leaders, and AI teams
  • Translate complex AI and data workflows into clear business value propositions
  • Collaborate with product, operations, and delivery teams to ensure seamless client onboarding and retention
  • Forecast revenue accurately and manage pipeline performance using CRM tools
  • Expand existing accounts through upselling, cross-selling, and long-term strategic partnerships
  • Represent the organization at industry events, conferences, and networking forums
  • Contribute to refining pricing strategies, go-to-market plans, and competitive positioning

What Makes You a Great Fit

  • 8+ years of experience in enterprise B2B sales, preferably in AI, data annotation, SaaS, or technology services
  • Proven track record of consistently exceeding revenue targets and closing high-value deals
  • Strong understanding of AI/ML ecosystems, model training workflows, and data lifecycle processes
  • Experience selling into technical buyers including AI teams, product managers, and engineering leaders
  • Exceptional negotiation, presentation, and stakeholder management skills
  • Ability to build scalable sales processes and mentor junior sales professionals
  • Strategic mindset with strong analytical and pipeline management skills
  • Comfortable operating in high-growth or emerging technology environments
  • Strong network within US technology and AI ecosystems is a plus
  • Self-driven, results-oriented leader with strong ownership and accountability
Posted 2026-02-28

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