Director, Enterprise Sales — Frontier AI Labs & Data Services

Annotera; San Francisco (CA); Hybrid; USD 180,000 - 260,000; Full time

Job summary

Annotera, based in the San Francisco Bay Area, seeks an experienced enterprise sales leader to own strategic growth at the intersection of AI data services and the frontier AI ecosystem.

You will lead new-business efforts, drive paid pilots, and cultivate long-term partnerships with frontier AI labs and multimodal AI companies. This hands-on role requires building account plans, negotiating contracts, and maturing pilots into recurring programs.

Qualifications

• 8+ years of enterprise sales or strategic business development experience.
• Established, active network of frontier AI labs and buyers.
• Proven record of originating and closing complex enterprise contracts, including seven-figure AI data or related services.
• Experience selling AI training data, annotation, or related AI services.
• Ability to discuss SFT, RLHF, evaluation design, and multimodal workflows with technical stakeholders.

Responsibilities

• Build and execute account strategies targeting frontier AI labs and AI developers.
• Activate relationships with leaders in data acquisition, model evaluation, and procurement.
• Lead full sales cycle from introductions to production contracts, including paid pilots.
• Define pricing, timelines, and capacity with solution architects and delivery teams.
• Expand initial projects into recurring programs across models, languages, and domains.

Skills

Enterprise sales

Strategic BD

AI labs

Contract negotiations

Large deals

Job description

• Full Time

The Opportunity

Lead strategic growth at the intersection of enterprise sales, AI data services, and the rapidly evolving frontier AI ecosystem. Annotera is seeking an experienced enterprise sales leader with deep, active relationships across frontier AI labs and the broader foundation-model ecosystem.

This is a hands-on new-business leadership role focused on opening strategic accounts, winning paid pilots, and building long-term, high-value partnerships for AI data services. You will need to understand how AI labs source training and evaluation data, identify the people who influence purchasing decisions, and translate technical requirements into scalable commercial programs.

As a senior individual contributor, you will own strategic business development and enterprise sales while having the potential to build a dedicated sales team as the business grows.

What You Will Own

• Build and execute an account strategy targeting frontier AI labs, foundation-model developers, and multimodal AI companies.
• Activate existing relationships with leaders in data acquisition, post-training, model evaluation, research operations, and procurement.
• Sell solutions spanning data annotation, supervised fine-tuning datasets, human preference feedback, expert evaluation, multilingual data, and multimodal data collection.
• Lead the full sales cycle: introductions, discovery, technical scoping, proposals, paid pilots, negotiations, and production contracts.
• Partner with solution architects and delivery teams to define quality standards, acceptance criteria, pricing, timelines, and capacity requirements.
• Expand initial projects into recurring programs across models, modalities, languages, and specialist domains.
• Maintain disciplined account plans, pipeline reporting, and revenue forecasts.
• Bring buyer feedback into service development, particularly around expert talent, data quality, turnaround time, and secure delivery.

What You Bring

• Based in the San Francisco Bay Area, with the ability to meet customers regularly in person.
• Typically 8+ years of enterprise sales or strategic business development experience, including direct sales into AI labs or advanced AI teams.
• An established, active network of relevant buyers and technical decision-makers within frontier AI labs.
• A proven record of personally originating and closing complex enterprise contracts, ideally including seven-figure AI data or related services engagements.
• Experience selling AI training data, annotation, human evaluation, expert talent, or closely related AI infrastructure and services.
• Enough technical fluency to discuss SFT, RLHF, preference data, evaluation design, and multimodal workflows with technical stakeholders.
• Strong commercial judgment around project economics, quality commitments, procurement, and contract negotiations.
• The ability to operate independently while coordinating closely with global delivery teams.

Preferred Background

Experience at an AI data services provider, an expert talent platform serving AI labs, or an AI infrastructure company with direct exposure to lab purchasing decisions. Experience taking an account from an initial pilot to a substantial recurring relationship is especially valuable.

What Success Looks Like

• First 90 days: Develop prioritized account plans, activate relevant relationships, qualify opportunities, and build a credible pilot pipeline.
• By six months: Secure paid pilots and initial contracts, with clear paths to production expansion.
• By twelve months: Establish recurring strategic accounts, deliver agreed revenue and gross-margin targets, and build a repeatable approach to winning additional lab customers.

Why Join Annotera?

This is an opportunity to take a leadership role in building strategic enterprise relationships across the frontier AI ecosystem. As Director, Enterprise Sales, you will work at the intersection of AI data services, enterprise sales, and emerging AI technologies, helping shape how Annotera engages with organizations developing and advancing foundation models.

The role gives you the scope to take ownership of strategic accounts from initial introductions and paid pilots through production contracts and long-term partnerships. You will work closely with solution architects and global delivery teams to translate customer requirements into scalable programs while bringing market and buyer insights back into the development of AI data services.

With the potential to build a dedicated sales team as the business grows, this role offers an opportunity to combine hands-on enterprise selling, strategic account development, commercial leadership, and team-building within a rapidly evolving AI services landscape.