Job Overview
Location
USA
Job Type
Full-time
Category
Sales Manager
Date Posted
February 24, 2026
Full Job Description
📋 Description
- • Join Toloka AI, a rapidly growing company at the forefront of creating data that powers cutting-edge Generative AI models. We are a dynamic startup with a strong financial backing and an impressive portfolio of clients, including Big Tech companies, renowned AI startups, enterprises, and non-profit research organizations globally. Our innovative approach combines domain experts, a diverse global crowd, and a sophisticated tech platform to teach AI models to reason. With experts in over 20 specialized domains and a crowd spanning 100 countries and 40 languages, we are uniquely positioned to tackle complex AI challenges.
- • We are a remote-first organization with a team of 200 talented individuals distributed worldwide, fostering a collaborative and flexible work environment. Our presence extends across the USA, UK, the Netherlands, Israel, Czech Republic, Serbia, and beyond, with physical offices in Amsterdam and Belgrade.
- • As we reinvent our Go-To-Market (GTM) strategy under new leadership, we are seeking ambitious and driven individuals to spearhead our next phase of growth. This is an exceptional opportunity to make a significant impact in a complex and rapidly evolving industry.
- • The Director of Sales – Enterprise AI will play a pivotal role in driving new business acquisition and expanding our footprint within enterprise accounts. You will be responsible for engaging with potential clients, deeply understanding their unique machine learning challenges, and architecting repeatable, value-driven solutions.
- • This role requires a proactive and strategic approach to sales, focusing on building strong relationships and demonstrating Toloka AI's capabilities to solve complex data annotation and AI training needs.
- • You will collaborate closely with cross-functional teams, including engineering, delivery, customer success, and product, to ensure seamless execution and deliver exceptional value to our prospects and clients.
- • Key responsibilities will include identifying and qualifying new business opportunities through proactive prospecting and pipeline management, ultimately leading to successful deal closures.
- • You will also be instrumental in growing existing accounts by identifying and capitalizing on upsell and cross-sell opportunities, as well as ensuring high renewal rates.
- • A core part of your role will involve leading commercial discussions, expertly uncovering client pain points, and structuring bespoke project proposals that align with their strategic objectives.
- • Developing and nurturing long-term client relationships will be paramount, requiring a consultative sales approach and effective management of sales cycles.
- • You will contribute to our sales operations by providing valuable competitive intelligence and actively participating in the RFP (Request for Proposal) process, ensuring our proposals are compelling and differentiated.
- • This position offers the chance to work with some of the most advanced AI technologies and influential organizations in the world, contributing directly to the advancement of artificial intelligence.
- • We are looking for a seasoned sales professional who thrives in a fast-paced startup environment and possesses a deep understanding of the enterprise technology landscape.
- • Your ability to articulate complex technical concepts in a clear and concise manner, coupled with a strong business acumen, will be crucial for success.
- • This is more than just a sales role; it's an opportunity to shape the future of AI data solutions and build lasting partnerships with industry leaders.
- • You will be empowered to take ownership of your territory, drive strategic initiatives, and contribute to the overall success of our sales organization.
- • We value a collaborative spirit and encourage you to bring your innovative ideas to the table as we continue to scale and evolve.
- • The ideal candidate will be a self-starter, highly motivated, and possess a proven track record of exceeding sales targets in the enterprise technology sector.
- • This role is based remotely in the USA, offering flexibility and the opportunity to work from anywhere within the country.
🎯 Requirements
- • Proven track record of exceeding quota-based sales targets in the enterprise technology space for at least five years.
- • Demonstrated experience in new business development, including prospecting, pipeline management, and closing complex deals.
- • Strong understanding of AI, Machine Learning, and Generative AI technologies, including market trends and fundamental concepts.
- • Experience selling into enterprise-level clients, understanding their business needs and technical requirements.
- • Background in a STEM field (e.g., Computer Science, Mathematics, Physics) is highly desirable.
- • Experience within a tech startup environment, demonstrating adaptability and a results-oriented mindset.
🏖️ Benefits
- • Competitive salary and performance-based bonuses.
- • Comprehensive health, dental, and vision insurance.
- • Generous paid time off and holidays.
- • Opportunities for professional development and continuous learning.
- • Remote-first work environment with flexibility.
Skills & Technologies
Remote
About Toloka AI, Inc.
Toloka AI, Inc. operates a global data-labeling and human-in-the-loop platform that combines machine learning with crowdsourced human intelligence to generate high-quality training data for computer vision, NLP, search, and other AI applications. The company offers scalable annotation workflows, quality control systems, and expert taskers across 100+ countries to help enterprises and research teams accelerate model development and improve accuracy. Founded in 2014 and headquartered in Amsterdam, Toloka serves technology giants and startups in e-commerce, autonomous vehicles, finance, and healthcare sectors.
