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General Manager, AI Data Labeling

Wing Assistant
California, CA Full Time
POSTED ON 11/28/2025
AVAILABLE BEFORE 1/27/2026

General Manager, AI Data Labeling

Remote, San Francisco


About Wing

Wing is one of the world's largest virtual talent companies, venture-backed and based in San Francisco. Leveraging our scale, millions of applicants, and other operational expertise, we’re launching a dedicated AI data labeling & annotation subsidiary, empowering exceptional people to play a defining role in training the next generation of AI. We’re hiring a General Manager to run this business end-to-end.


About the Role

As General Manager, AI Data Labeling, you will own P&L, strategy, go-to-market, delivery/quality, security & compliance, and team building. You’ll build the business from zero, close key customers, help set up the operating engine, and report directly to Wing’s CEO. 


Responsibilities:

- Acquire new business from AI labs and tier-1 tech companies via your network, digital/in-person outbound

- Own enterprise sales cycles end-to-end (discovery, scoping, pricing, MSA/SOW negotiation)

- Attend meetings, consultations, events, etc. in person as needed and build key relationships

- Build durable relationships with researchers, data/infra leaders, procurement, and legal; expand accounts

- Own the business plan, pricing, margin targets, forecasting, and budget adherence.

- Report on progress to senior leadershipFoster a culture of accountability, transparency, and operational rigor


Requirements:

- Primarily located in San Francisco, CA, with a willingness to travel around Northern California, the United States, and internationally as needed

- Bachelor's degree in any discipline, ideally from a top institution

- Outgoing, social, gregarious personality, willingness, and capability to always be building relationships

- Great management skills: you will, to an extent, be responsible for a giant piece of an entire business unit and all that comes with it, people management, budgets, interfacing with finance, legal, operations, and more

- Strong preference for someone who has led Sales & Commercials: Expert in complex MSAs/SOWs, pricing, and margin managementTrusted relationships across AI labs and leading tech companies; able to open doors and close enterprise deals

- Expert in complex MSAs/SOWs, pricing strategy, and margin managementProven builder of multidisciplinary teams; excellent stakeholder managementDigital native (Google Workspace, Sheets, CRM)


Nice-to-haves:

- Experience selling to or operating within AI labs (RLHF, red-teaming, evals, multimodal)

- Prior success taking a services P&L from $0 to $10M with healthy unit economics

- Strong interest and understanding in artificial intelligence, machine learning, and LLMs

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$170,000 - $250,000 a year
Benefits & Compensation:
- Base compensation: $170K–$250K, with increases as the business grows
- Equity: generous grant vested over 4 years
- Performance Bonus: Strong performers can expect $300K-$1M in additional annual cash and equity on top of base for closing and expanding enterprise deals
- A $1K monthly allowance for meals
- Company-sponsored Equinox membership
- Health insurance
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Note: please ignore any interview assessment automated emails, if any. They do not apply to this role.

Salary.com Estimation for General Manager, AI Data Labeling in California, CA
$112,910 to $141,270
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