Associate Chatbot Trainer (Temporary/Project-based)

Remote USA

Full Time Mid-level / Intermediate
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We are looking for an Associate Chatbot Trainer to work with Directly on our DARWIN team! This is a 3-6 month-long, hourly project where you will participate in building and optimizing chatbot technology. Directly is excited to launch our newest chatbot technology and we need your help in building and training our chatbot natural language models and performing the quality review of crowdsourced work and Virtual Assistant performance. You would also have the opportunity to participate in the operational management of the crowd that will help build the Virtual Assistants.


  • Review questions from Directly’s end-users and assist in the categorization of these questions and topics
  • Perform quality review of crowdsourced work and automation transcripts
  • Utilize data-mining methods in order to identify opportunities for improvement in our chatbot knowledge-base
  • Test our AI software and provide feedback to Product team
  • Assist in operational management of onboarding, coaching and providing customer support to chatbot trainer crowd members


  • Excellent comprehension skills and highly organized
  • High attention to detail with an analytical mindset
  • Exceptional written and verbal communication skills 
  • Inquisitive with strong problem solving skills
  • Collaborative team member with a positive attitude
  • College Degree 
  • Intermediate computer skills (Excel, Google Sheets, etc.) / technical acumen
  • 1-2+ years professional experience in the customer support space, chatbot space, or in an analytical role

Bonus Points:

  • Information Architecture
  • Exposure to / understanding of NLP and Machine Learning technologies
  • Experience with SQL and Data Analysis


  • 3-6 month project
  • Paid hourly
  • Needed ASAP

At Directly, we are committed to building a dynamic and inclusive community where everyone can do the best work of their lives. Directly is an equal opportunity employer and committed to creating an inclusive environment. We hire, develop, and retain the most talented individuals by celebrating our diverse cultures, perspectives, skills, and experiences.______________________________________________________________________________________________
Directly is a pioneer in customer service for many of the world’s leading brands. Many of the world’s leading brands partner with Directly to support customers with cutting-edge AI and on-demand customer service that consumers love.
Companies like Airbnb, Microsoft, and Samsung improve their customer experience, boosting CSAT by up to 20% while significantly reducing contact center volume and saving millions per year.
Directly is based in San Francisco and backed by Microsoft’s M12 Ventures, Samsung NEXT, True Ventures, Costanoa Ventures, Industry Ventures, Triangle Peak Partners, and Northgate Capital.
We have an amazingly talented team focused on collaboration and melding together creativity, technology, and data-driven insights. Come join us and contribute to our culture of curiosity, authenticity, and innovation!
Job region(s): North America
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