Director of Strategy & Operations

About Toloka

At Toloka AI we create data that powers leading GenAI models and innovations. We work with frontier labs, big tech, renowned AI startups, enterprises and non-profit research organizations worldwide. We use a combination of Experts + Crowd + Tech Platform to teach AI models to reason and evaluate their efficacy and safety. We have experts in more than 50 different domains—from doctors and lawyers to physicists and engineers—and boast one of the most diverse global crowds, representing over 100 countries and speaking 40+ languages. We are a well-funded startup with an enviable portfolio of clients including Anthropic, Amazon, Microsoft, Poolside, Recraft, and Shopify.

Recently, we secured strategic investment led by Bezos Expeditions and Nebius Group with participation from Mikhail Parakhin, CTO of Shopify and board advisor to leading GenAI companies, who now serves as our Chairman of the Board. Our remote-first team is globally distributed around the world: USA, UK, the Netherlands, Serbia, and more.

About the position

You'll be the CSO's main partner on how Toloka goes to market. The job has three parts: decide what we sell and to whom, get new commercial processes running across teams, and give the exec team revenue reporting they can rely on.

This is not a support role. You'll own the analysis behind major commercial decisions and see them through to execution.

What you'll do

GTM strategy and offerings

• Own the strategic view of our GTM offerings: what we sell, to whom, and at what price.
• Run the market and competitor research behind it.

Cross-functional process launches

• Launch new commercial processes across Sales, Delivery, Legal and Finance, and make sure people actually use them.

Revenue reporting for executives

• Build and own exec revenue reporting: bookings, revenue, pipeline, forecast and margin.
• Run the weekly, monthly and quarterly business reviews with the CSO.

Advisor to the CSO

• Prepare the CSO for board and exec discussions, and push back when needed.
• Help the CSO decide where to put people and budget: which deals, offerings and markets get them.

What success looks like in your first 6 months

• The exec team uses one revenue report every week, and nobody argues about whose numbers are right.
• Leadership has agreed on a clear map of our GTM offerings: what we sell, to whom, and at what price.
• At least two new cross-functional processes are live and in use by Sales, Delivery, Legal and Finance.

What we're looking for

Must have

• Several years in Strategy & Operations, BizOps, RevOps or GTM strategy, ideally in B2B tech with enterprise sales.
• You've built revenue reporting that execs relied on, and launched processes across teams that stuck.
• Strong with numbers. You build your own models.
• Solid understanding of AI and how models are trained and evaluated.
• Quantitative degree: engineering, computer science, maths, physics or similar.

Nice to have

• Startup or founder experience.
• Background in an AI or data company.