Chief of Staff, Commercial & AI Training GTM Lead

About the Role

This role reports directly to the SVP of Commercial and carries two distinct mandates.

First and foremost (roughly two-thirds of the role): Lead the commercial build and execution of a new AI training business. This position will own this go-to-market motion end to end—setting the strategy and personally executing it, from building pipeline through closing deals.

Second: Drive commercial strategy work for the broader sales organization. This includes leading outbound initiatives and running high-impact strategic projects across the wider commercial team.

On the AI training side, the company is transforming its expert network into the evaluation, post-training, and audit data that enterprises and AI labs need to deploy AI in production. This is a new business unit—spanning offerings like Domain Eval Sprints, Custom Data Solutions, Model Behavior Audits, Agentic RL Environments, and Domain QA-as-a-Service—and this role will be responsible for taking it to market. The individual will shape the positioning and approach, then run it themselves: building the pipeline, doing the outreach, holding the calls, and closing the deals. This position will work hand in hand with delivery, product, marketing, and legal to establish everything a new commercial line needs, and will manage a small team as the business scales.

This is an unusual mandate: part strategist, part operator, part closer. It suits someone who wants to build a business rather than inherit one, and who is equally comfortable designing the plan and doing the work. It offers direct exposure to the AI frontier, senior leadership, and a fast track toward commercial and operational leadership within the organization.

Location: Remote (US or Canada) or Hybrid (New York City)

Responsibilities

• Lead the commercial build and execution of the AI training business
• Own the go-to-market strategy and its execution. Define how the company will position, package, and sell its AI training offerings across customer archetypes (AI-native scaleups, Fortune 500 AI teams, mid-tier labs, and frontier labs)—and then run it yourself, from first touch through closed-won.
• Sell and close. Build and work the pipeline, run first conversations, scope opportunities against capabilities, submit proposals, and close pilots and multi-engagement agreements. This role is both the strategist and the seller.
• Partner across the company to stand up the business. Work with marketing on collateral and brand presence, with legal on MSAs, SOWs, and security/compliance packets, and with delivery to ensure flawless execution on what is sold.
• Shape the product and capabilities. Act as the voice of the market, bringing prospect feedback back to product and leadership to refine pricing, packaging, and roadmap as the company builds toward direct engagements with AI labs and large enterprises.
• Build and manage the team. Direct day-to-day commercial execution (prospecting, enrichment, outreach) and manage a small, growing team.
• Drive commercial strategy for the broader sales organization
• Lead outbound initiatives. Own and oversee outbound programs aimed at winning new business—new logos and new buyers at existing accounts—across the wider commercial organization.
• Run strategic commercial projects. Operate as the SVP of Commercial’s core “get-things-done” resource: independently scope and lead high-impact projects that optimize top-line growth and operational efficiency across the sales organization.
• Turn analysis into action. Bring structured, analytical rigor to ambiguous problems, then drive recommendations through to implementation.

Requirements

• 3-5 years of management consulting experience at a top-tier firm, ideally with exposure to commercial, growth, or go-to-market work.
• An analytical operator. Excels at working through large, ambiguous problems independently and seeing them through from strategic ideation to execution. Problem solving is the primary M.O.
• Commercially minded and willing to carry a number. Energized by owning a revenue outcome and comfortable being the one who runs the call and closes the deal. Direct sales, business development, or client-facing experience is a significant advantage.
• A builder. Wants to stand something up from scratch—processes, pipeline, collateral, a team—rather than manage an established machine.
• A fast learner in technical domains. Can get fluent quickly on how modern AI models are trained and evaluated (evals, SFT, RLHF, and related concepts) and hold their own with technical buyers. Knowledge of the AI model training and data labeling space is a significant advantage.
• An exceptional communicator. Writes clearly and succinctly, and thrives presenting in high-stakes situations to both C-level and technical audiences.
• Resilient and adaptable. Works efficiently with minimal direction and under pressure. When things change or a deal stalls, the individual rolls with the punches and finds a new angle.
• A collaborator and emerging leader. Works well across internal teams and is ready to manage and mentor others.
• Valid US or Canadian work authorization required. Visa sponsorship is not available for this role.

Benefits

• Competitive compensation: base salary, performance bonus, and participation in the company stock program
• Massive impact: the chance to build a brand-new business unit from the ground up with direct C-level influence at an extremely fast-growing late-stage startup
• Fast-track career growth toward commercial and operational leadership
• Excellent medical, dental, and vision insurance
• 401k match with immediate vesting
• Health savings/flexible savings account, and pre-tax commuter benefits
• Paid time off: vacation, holidays, sick, and parental leave
• A diverse, collaborative, and positive culture where investment in and celebration of each other’s success occurs (happy hours, team projects, and retreats)