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Remote Cto Jobs in Kentucky (NOW HIRING)

Toloka

... , 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 ...

On Plane Consulting

Director of Product

Louisville, KY · Remote

$203K - $213K/yr

Ourscalable, easy to use platform helps our customers leverage best in classmarketing technology to ... This role will report to the CEO. They must be a strong servant leader who will build consensus and ...

Distro

$4.0K - $5.0K/mo

Remote Reports to: CEO Team: 2-3 engineers About the role Distro is an AI-powered recruiting ... ATS, HR tech, or recruiting domain knowledge * Infrastructure as code (CloudFormation, Terraform ...

True North Recruiters

Let's Get to Work

Frankfort, KY · Remote

$89K - $115K/yr

Remote (Work From Anywhere) Compensation: 100% Commission -- Uncapped Income Potential Experience ... Manage your own schedule and pipeline -- you're the CEO of your business * Continuously grow your ...

True North Recruiters

Let's Get to Work

Lexington, KY · Remote

$101K - $131K/yr

Remote (Work From Anywhere) Compensation: 100% Commission -- Uncapped Income Potential Experience ... Manage your own schedule and pipeline -- you're the CEO of your business * Continuously grow your ...

True North Recruiters

Let's Get to Work

Louisville, KY · Remote

$98K - $127K/yr

Remote (Work From Anywhere) Compensation: 100% Commission -- Uncapped Income Potential Experience ... Manage your own schedule and pipeline -- you're the CEO of your business * Continuously grow your ...

C-Plan.IT

VP Engineering and R&D - AI Startup

Louisville, KY · Remote

$172K - $221K/yr

Privately funded, we are a fully remote company with a 100% distributed team allowing us to hire ... Serve as a thought leader and technology strategy driver along with the CEO and Co-Founders to make ...

C-Plan.IT

VP Engineering and R&D - AI Startup

Louisville, KY · On-site +1

$172K - $221K/yr

Privately funded, we are a fully remote company with a 100% distributed team allowing us to hire ... Serve as a thought leader and technology strategy driver along with the CEO and Co-Founders to make ...

Priority1

Territory Manager-Remote

Warsaw, KY · On-site +1

... CEO, CFO, President, and Vice President. This outside sales position is focused on new business acquisition. The freight shipping industry has an unlimited prospect base. The Priority1 value ...

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All JobsCto JobsRemote Cto JobsRemote Cto Jobs in Kentucky

Remote Cto information

See Kentucky salary details

$22.1K

$144.6K

$240.1K

How much do remote cto jobs pay per year?

As of Aug 31, 2026, the average yearly pay for remote cto in Kentucky is $144,619.00, according to ZipRecruiter salary data. Most workers in this role earn between $114,600.00 and $169,400.00 per year, depending on experience, location, and employer.

What is a remote CTO?

Remote CTOs, or Chief Technology Officers, are executive leaders who oversee a company's technology strategy and operations while working remotely rather than on-site. They are responsible for guiding the technical vision, managing development teams, making high-level architecture decisions, and aligning technology initiatives with business goals. Remote CTOs may work full-time for a single company or serve multiple clients as fractional or interim CTOs. Advances in collaboration tools and cloud technologies have made it increasingly common for CTO roles to be performed remotely, especially in startups and tech-focused organizations.

What does a remote CTO do?

As a remote CTO or Chief Technology Officer, you are responsible for your company’s vision and strategy with regards to all things technology, and your duties revolve around managing the technical infrastructure of your company. You develop and implement plans for hardware and software upgrades, maintenance, and deployment, and you manage the IT support desk, working to ensure consistent availability of computer resources for your team members throughout the organization. Additionally, you are typically responsible for information security, strategic decisions around IT investments, and policy development. As a remote employee, you telecommute from a satellite office or work from home.

What are the key skills and qualifications needed to thrive as a remote CTO?

To thrive as a Remote CTO, you need deep expertise in software architecture, leadership experience, and a track record of guiding technology strategy, often supported by a degree in computer science or related fields. Familiarity with cloud platforms, DevOps tools, and project management systems like Jira or Trello is essential, and certifications such as AWS Certified Solutions Architect can be advantageous. Exceptional communication, strategic thinking, and the ability to lead and inspire distributed teams are crucial soft skills. These skills ensure effective decision-making, seamless remote collaboration, and successful delivery of technology initiatives in a virtual environment.

How does a remote CTO effectively lead and communicate with distributed engineering teams?

As a Remote CTO, effective leadership hinges on clear, consistent communication and establishing structured processes for virtual collaboration. Utilizing project management tools, regular video meetings, and clear documentation helps ensure everyone stays aligned on goals and progress. Building trust and fostering a culture of transparency are especially important in remote settings, as is providing mentorship and support across different time zones. Proactively addressing challenges related to distance and asynchronous work enables a Remote CTO to maintain team cohesion and drive technological success.

What is the difference between Remote Cto vs Remote Software Engineer?

AspectRemote CtoRemote Software Engineer
Required CredentialsTypically requires extensive experience in software development, leadership, and strategic planning; often a bachelor's or master's in CS or related fieldUsually requires a bachelor's degree in CS, software engineering, or related field; experience varies
Work EnvironmentExecutive leadership role overseeing entire tech strategy; collaborates with C-suite and stakeholdersIndividual contributor role focused on coding, testing, and implementing software solutions
Employer & Industry UsageUsed in tech companies, startups, and enterprises for strategic tech leadershipCommon across tech companies, startups, and organizations needing software development

The main difference between a Remote Cto and a Remote Software Engineer lies in their responsibilities and seniority. The Remote Cto focuses on strategic technology leadership and decision-making, while the Remote Software Engineer concentrates on developing and implementing software solutions. Both roles are vital in tech organizations but serve different functions within the company's hierarchy.

More about Remote Cto jobs

What are the most commonly searched types of Cto jobs in Kentucky?

The most popular types of Cto jobs in Kentucky are:

What are popular job titles related to Remote Cto jobs in Kentucky?

For Remote Cto jobs in Kentucky, the most frequently searched job titles are:

What cities in Kentucky are hiring for Remote Cto jobs?

Cities in Kentucky with the most Remote Cto job openings:

Remote Cto jobs near you
Infographic showing various Remote Cto job openings in Kentucky as of August 2026, with employment types broken down into 91% Full Time, 6% Part Time, and 3% Contract. Highlights an 80% Physical, 5% Hybrid, and 15% Remote job distribution, with an average salary of $144,619 per year, or $69.5 per hour.

Freelance Technical Consultant

Toloka

Remote

Full-time

Re-posted 4 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!
To learn how we collect, use, disclose, and store personal data, check out our Privacy Notice.

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