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Remote First Companies Jobs in Kentucky (NOW HIRING)

Toloka

... 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 Role Technical ...

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What are some common challenges when working for remote first companies, and how can employees overcome them?

Working for remote-first companies can present challenges such as feelings of isolation, difficulty in communication across time zones, and maintaining work-life balance. Employees can overcome these by proactively engaging in virtual team meetings, using collaboration tools effectively, and establishing a dedicated workspace at home. Many remote-first organizations also encourage regular check-ins and virtual social events to foster connection and teamwork. By being intentional about communication and setting clear boundaries, employees can thrive in a remote-first environment.

What are the key skills and qualifications needed to thrive at a remote first company?

To thrive at a remote-first company, you generally need strong self-management, digital communication, and time management skills, along with relevant qualifications for your specific role. Familiarity with collaboration tools like Slack, Zoom, project management platforms, and cloud-based systems is essential. Proactive communication, adaptability, and a high degree of self-motivation are standout soft skills in remote environments. These abilities are crucial for maintaining productivity, clear team alignment, and effective collaboration without the structure of a traditional office.

What are remote first companies?

Remote first companies are organizations that prioritize remote work as the default mode of operation for their employees. This means that most work is designed to be done from anywhere, with physical office spaces being optional or used primarily for collaboration when necessary. Such companies invest in digital tools and communication processes to support distributed teams, ensuring equal access and opportunities for all employees regardless of location. The remote-first approach can help attract top talent, reduce overhead costs, and promote a better work-life balance.

What is the difference between Remote First Companies vs Remote Customer Support Representatives?

AspectRemote First CompaniesRemote Customer Support Representatives
Work EnvironmentCompany-wide remote work culture, flexible policiesIndividual remote role within a company, often flexible hours
Required CredentialsVaries by industry, often includes general business or tech skillsCustomer service experience, communication skills, sometimes technical knowledge
Industry UsageAcross tech, marketing, finance, and morePrimarily in tech, e-commerce, and service sectors

Remote First Companies are organizations that prioritize remote work across all departments, fostering a flexible, distributed work culture. Remote Customer Support Representatives are individual roles within such companies, focused on assisting customers remotely. While both share remote work environments, Remote First Companies emphasize company-wide policies, whereas Customer Support roles are specific job functions within these organizations.

What cities in Kentucky are hiring for Remote First Companies jobs? Cities in Kentucky with the most Remote First Companies job openings:
Remote First Companies jobs near you
Infographic showing various Remote First Companies job openings in Kentucky as of August 2026, with employment types broken down into 94% Full Time, 3% Part Time, and 3% Contract. Highlights an 100% Remote job distribution.

Freelance Technical Consultant

Toloka

Remote

Full-time

Re-posted 13 days ago

Job description

Company Intro

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 Role

Technical consultants play a key role in our company, ensuring top-level delivery of our product, its correct configuration, and the deployment of tailored AI data solutions that meet our customers' needs and deliver an exceptional experience working with us.
As part of this role, you will not only design and implement data labeling pipelines but also act as a trusted technical advisor for our customers - helping them understand their data needs, discover new opportunities, and build scalable AI solutions.
We are looking for a person with more than 3 years of solid technical background, who feels comfortable working in technical environments, solving data-related tasks using Python and AI, and communicating directly with customers. You should be a confident communicator able to engage with both technical and executive stakeholders and collaborate closely with our commercial team.

Responsibilities1. Client Ownership & Communication
  • Act as the primary technical point of contact for customers across technical and executive stakeholders.
  • Lead discovery conversations to deeply understand client goals, problems and quality criteria.
  • Translate client needs into clear, actionable solution designs and delivery plans.
  • Advise customers on best practices in data collection, data quality, evaluation, and model training workflows.
  • Set expectations proactively, communicate progress regularly, and manage risks and trade-offs transparently.
  • Identify expansion opportunities and additional ways Toloka can create value through data and AI solutions.
2. Solution Design & Delivery
  • Design end-to-end data solutions using Toloka's platform, selecting appropriate components, workflows, and quality controls.
  • Configure data labeling components and quality controls, develop user interfaces and AI-driven tooling (e.g. agentic systems, RAGs, synthetic data generation), and integrate them into end-to-end automated pipelines for AI training and evaluation.
  • Run experiments and pilots to validate quality, throughput, and cost assumptions.
  • Lead technical execution during delivery, coordinating internal teams and external stakeholders as needed.
  • Ensure solutions meet agreed quality, performance, and scalability requirements.
3. End-to-End Ownership & Project Management
  • Own delivery outcomes holistically - including technical performance, quality, timelines, and financial efficiency.
  • Monitor key KPIs (e.g. throughput, quality metrics, Gross Margin, Contribution Margin) and act on deviations.
  • Prioritize work based on customer impact and business value.
  • Analyze data to identify failure modes, inefficiencies, and opportunities for improvement.
  • Continuously optimize solutions through iteration, automation, and adoption of new technologies.
  • Troubleshoot delivery, process, or technical issues in collaboration with support, infrastructure, and product teams.
  • Drive solutions toward stable operation with minimal ongoing maintenance.
RequirementsCore Experience
  • Experience as a Solution Engineer, Technical Solutions Engineer, Data Scientist, Data/Systems Analyst, or Technical Project Manager.
  • Proven experience owning projects end-to-end, including scoping, delivery, and stakeholder management.
  • Direct experience working with external customers on technical projects (requirements gathering, delivery, iteration).
Technical Skills
  • Strong Python skills for data manipulation (e.g. NumPy, pandas), natural language processing (e.g. NLTK, spaCy), and building lightweight web services or tools (e.g. FastAPI, Flask).
  • Solid understanding of ML concepts and data workflows; familiarity with LLMs and prompt engineering is a strong plus.
  • Experience designing multi-stage pipelines and complex systems.
  • Understanding of software development fundamentals: version control, testing, MVPs, iterative development etc..
  • Bachelor's or Master's degree in Data Science, ML/AI, Software Engineering, or a related quantitative field such as Physics or Applied Mathematics, with strong analytical foundations.
  • Ability to reason about trade-offs between quality, speed, cost, and scalability.
Communication & Ownership
  • Excellent English communication skills (B2+), with the ability to explain complex technical concepts to non-technical audiences.
  • Confidence working with data engineers, ML engineers, and researchers from leading tech companies.
  • Strong ownership mindset: comfortable being accountable for outcomes, not just tasks.
  • Ability to manage multiple projects in fast-paced, ambiguous environments.
Nice to have
  • Experience with crowdsourcing, expert workflows, or large-scale data labeling.
  • Experience working on ML training, evaluation, or agentic systems.
  • Familiarity with quality frameworks, audits, or data validation pipelines.


[Important Notice] Scam Alert Regarding Fake Job Postings

It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants.Please be aware:

  • Official Communication: Our recruiting team will only contact you from an official "toloka.ai" email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc,  or other personal or seemingly business email accounts.
  • Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process.
  • Official Listings: All legitimate job openings are posted on our official careers page: https://toloka.ai/careers#job-list
What to do: If you see a suspicious job posting or have been contacted by someone you suspect is a scammer, please do not provide any personal information. Instead, report the incident to us directly at security@toloka.ai and report the profile/post to LinkedIn.We are taking this matter very seriously and are working with the appropriate parties to resolve it.
Thank you for your vigilance!

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