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ai trainer/data annotator - remote Jobs in Chicago

ai trainer/data annotator - remote

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assistant controller - remote

ai trainer data annotator remote

YO IT Consulting

<div>
 Role Overview
 
 
 Collaborating with a leading AI lab to contract detail-oriented generalists for a data annotation project. Contractors will support the development of AI systems by categorizing and labeling diverse datasets using predefined taxonomies. The project offers an opportunity to directly contribute to the accuracy, reliability, and performance of next-generation AI models.
 
 
 Key Responsibilities
 
 
 <ul>
 <li>
 Synthesize information from large volumes of data
 </li>
 <li>
 Annotate and categorize text, images, and other data according to detailed guidelines
 </li>
 <li>
 Apply predefined rubrics and taxonomies to produce structured, high-quality outputs
 </li>
 <li>
 Flag inconsistencies, ambiguities, or errors in datasets
 </li>
 <li>
 Contribute to the improvement of AI systems through consistent annotation work
 
 
 </li>
 </ul>
 
 Ideal Qualifications
 
 
 
 <ul>
 <li>
 Ability to synthesize complex or high-volume information into structured formats
 </li>
 <li>
 Strong critical reasoning, reading comprehension, and written communication skills
 </li>
 <li>
 Prior experience applying rubrics, taxonomies, or standardized guidelines (preferred but not required)
 
 
 </li>
 </ul>
 More About the Opportunity
 
 
 <ul>
 <li>
 Expected commitment: ~20 hours/week
 
 
 </li>
 </ul>
 Application Process
 
 
 <ul>
 <li>
 Submit your resume to begin
 </li>
 <li>
 Complete a Training Assessment
 </li>
 <li>
 Typical response time: 1-2 business days
 
 
 </li>
 </ul>
 We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.
 
 
 Contract and Payment Terms
 
 
 <ul>
 <li>
 You will be engaged as an independent contractor.
 </li>
 <li>
 This is a fully remote role that can be completed on your own schedule.
 </li>
 <li>
 Projects can be extended, shortened, or concluded early depending on needs and performance.
 </li>
 <li>
 Your work will not involve access to confidential or proprietary information from any employer, client, or institution.
 </li>
 <li>
 Payments are weekly on Stripe or Wise, based on services rendered.
 </li>
 </ul>
</div>

Ai Trainer/Data Annotator - Remote

Applied Systems

<div>Job Description:

Amazing Career Moments Happen Here 
Transforming the insurance industry is ambitious, we know. That&rsquo;s why at Applied, we&rsquo;re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers &ndash; all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we&rsquo;re not just redefining what&rsquo;s achievable, we&rsquo;re creating a place where amazing career moments are made possible. 
Position Overview<div> 
We're seeking an Associate AI Engineer / AI Engineer to build and enhance data solutions and AI initiatives for the business of insurance.</div><div>
In this role, you will work closely with the Principal Data Architect, Data Scientists, and Software Engineers to build, model, and maintain data solutions as we optimize data architecture and accessibility of large-scale datasets for our global teams.</div><div></div><div> 
What You&rsquo;ll Do</div><ul><li>
Partner with Product, Engineering, and Data Science leaders to design and deliver AI-powered user experiences in our dashboard products</li><li>
Build and integrate conversational AI solutions (e.g., Vertex AI, Generative AI APIs) into Applied&rsquo;s products</li><li>
Use AI tools responsibly (e.g., code assistance, test generation, analysis, and documentation) to accelerate velocity and improve quality while validation outputs and ownership of contributions to the customer experience</li><li>
Work with Google Cloud APIs, Vertex AI, and related services to enable intelligent workflows</li><li>
Prototype and implement AI-driven insights and recommendations directly in dashboards for client use</li><li>
Collaborate with UX and product teams to design seamless user experiences powered by AI</li><li>
Support development of generative AI prototypes, prompt design, and fine-tuned models</li><li>
Stay current on advancements in Google Cloud, conversational AI, and applied AI engineering</li><li>
Assist senior engineers and scientists on larger initiatives to scale AI capabilities across the platform</li></ul><div> 
We&rsquo;re Excited to Learn More About You</div><div></div><ul><li> 
Hybrid: Ability to work from an Applied Systems office on an ad hoc basis, with remote work days for deep work.</li></ul><ul><li> 
Must have:</li></ul><ul><li>
Strong programming skills in Python and SQL.</li><li>
Exposure to data science concepts (predictive modeling, ML/AI basics, or coursework/projects).</li><li>
Interest in applied AI, conversational AI, and building user-facing insights.</li><li>
Familiarity with cloud platforms (Google Cloud preferred) or willingness to learn quickly.</li><li>
Understanding of APIs and how applications connect to each other.</li><li>
Problem-solving skills with curiosity and eagerness to experiment and explore new technologies.</li></ul><ul><li> 
Nice to have (but not required):</li></ul><ul><li>
Experience with Google Cloud tools such as Vertex AI, Dialogflow, or BigQuery.</li><li>
Familiarity with dashboards/visualization tools (Looker, Tableau, or Power BI).</li><li>
Version control knowledge (Git).</li></ul><ul><li> 
Education: Bachelor's or Master's degree in a related field (e.g., Computer Science, Data Science, Engineering, or related field)</li><li><ul><li>
We proudly support and encourage people with military experience, as well as military spouses, to apply.</li></ul></li></ul><div></div> 
When You Join Team Applied, You Can Expect: 
A culture that values who you are and recognizes that you aren&rsquo;t just an employee; you are a teammate, and you matter. We thrive on the benefits of our different experiences and celebrate the uniqueness our teammates bring to work with them every day. 
We flex our time together, collaborating remotely and in-person to empower our teams to work in the ways that work best for them. 
A comprehensive benefits and compensation package that centers our teammates and helps them to bring their best to work every day:<ul><li>
Medical, Dental, and Vision Coverage</li><li>
Holiday and Vacation Time</li><li>
Health &amp; Wellness Days</li><li>
A Bonus Day for Your Birthday</li></ul> 
 
Learn more about the people behind our products at https://www1.appliedsystems.com/en-us/about-us/jobs/ 
Our targeted starting base salary in the United States for this position ranges from $80,000 - $120,000. To determine a new team member&rsquo;s starting pay, we consider a variety of factors, including someone&rsquo;s depth, breadth, and variety of experience, skills, and responsibilities. Depending on the role, team members may also be eligible to participate in additional compensation plans such as bonus and commission. 
Your Security Matters: 
 Our candidates&rsquo; personal information and online safety are top of mind for us. At Applied, we proactively protect your personal information and only communicate with candidates via a secure @appliedsystems.com email or through our official careers portal. Recruiters will never request payments, ask for financial account information or sensitive information like social security numbers. 
EEO Statement
Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don&rsquo;t discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law. 
#LI-Hybrid</div><div></div>

Associate AI Engineer / AI Engineer

Turing

<div>
 
 
 About Turing
 
 
 
 Based in San Francisco, California, Turing is the world&rsquo;s leading research accelerator for frontier AI labs and a trusted partner for global enterprises deploying advanced AI systems. Turing supports customers in two ways: first, by accelerating frontier research with high-quality data, advanced training pipelines, plus top AI researchers who specialize in coding, reasoning, STEM, multilinguality, multimodality, and agents; and second, by applying that expertise to help enterprises transform AI from proof of concept into proprietary intelligence with systems that perform reliably, deliver measurable impact, and drive lasting results on the P&amp;L.
 
 
 
 
 
 
 Role Overview
 
 
 
 Turing is looking for Accounting professionals to work with our researchers to improve the performance of AI models. You will apply your expertise in financial reporting, audit, tax compliance, and accounting standards to evaluate and train AI systems. If you enjoy solving complex problems in accounting and are interested in shaping the future of AI in finance, please apply. No prior AI experience is required.
 
 
 
 
 
 
 What Does Day-to-Day Look Like
 
 
 <ul>
 <li>
 Evaluate LLM models on accounting topics such as revenue recognition, lease accounting, consolidation, and tax provision calculations.
 </li>
 <li>
 Create rubrics to assess model capabilities on tasks like journal entry analysis, financial statement preparation, audit procedures, and GAAP/IFRS compliance.
 </li>
 <li>
 Collaborate with AI researchers and fellow finance experts to shape training methods, evaluation strategies, and benchmarks.
 </li>
 </ul>
 
 
 
 
 
 Requirements
 
 
 <ul>
 <li>
 2+ years of experience in Accounting (e.g., public accounting, corporate accounting, audit, tax, or financial reporting).
 </li>
 <li>
 Strong grasp of US GAAP or IFRS, financial statement preparation, audit methodologies, and regulatory compliance.
 </li>
 <li>
 Excellent English written communication.
 </li>
 </ul>
 
 
 
 
 
 Bonuses (Not at All Necessary)
 
 
 <ul>
 <li>
 CA, CPA, ACCA, CMA, or MBA in Finance/Accounting.
 </li>
 </ul>
 
 
 
 
 
 Perks of Freelancing with Turing
 
 
 <ul>
 <li>
 Work on the cutting edge of AI and finance.
 </li>
 <li>
 Fully remote and flexible work environment.
 </li>
 <li>
 Competitive hourly compensation of ~$100+/hour depending on experience.
 </li>
 </ul>
 
 
 
 
 
 Offer Details
 
 
 <ul>
 <li>
 Commitment: Flexible, 10&ndash;30 hrs/week.
 </li>
 <li>
 Duration: ~1 month, with the possibility of extension based on performance and project needs.
 </li>
 </ul>
 
 
 
 
 
 
 
 
 After applying, you&rsquo;ll receive a login link by email. Please complete your profile promptly so we can proceed with your application.
 
 
 
 
 
 
 
 We&rsquo;re actively hiring for this role. If you know exceptional talent, please refer them at
 
 turing.com/referrals
 
 and earn money for successful referrals.
 
 
</div>

Remote Accounting Specialist ($100/hr) - 75409

Careers In Travel | Destination Planners

<div>
 
 Job Overview
 
 
 
 We are seeking a detail-oriented
 
 Remote Reservation Support Specialist
 
 to assist with client reservation requests and provide administrative support related to booking and scheduling services. This is a remote support role focused on customer service, coordination, and accurate data handling within a reservations environment.
 
 
 This position is ideal for individuals who are organized, professional, and comfortable working independently in a remote setting.
 
 
 
 Key Responsibilities
 
 
 
 Assist with reservation and scheduling requests submitted by clients
 
 
 Support booking coordination across various service categories, including accommodations and related services
 
 
 Maintain accurate client records and reservation details in internal systems
 
 
 Communicate professionally with clients via email, phone, or messaging platforms
 
 
 Provide general customer service support and follow established processes
 
 
 Review confirmations and documentation for accuracy and completeness
 
 
 Collaborate with internal teams to ensure a smooth client experience
 
 
 
 Qualifications
 
 
 
 Strong written and verbal communication skills
 
 
 Excellent attention to detail and organizational abilities
 
 
 Comfortable using online systems, email, and basic digital tools
 
 
 Ability to manage multiple tasks while meeting deadlines
 
 
 
 Customer Service Or Administrative Support Experience Preferred
 
 
 
 Reliable internet access and ability to work remotely
 
 
 
 Work Environment
 
 
 
 Fully remote position
 
 
 Flexible scheduling options may be available
 
 
 Supportive, structured team environment
 
 
 We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
</div>

Remote Reservation Support Specialist

<div><h2 class="jobSectionHeader">Description</h2>
<div>
Employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity. We will only consider candidates who are currently authorized to work in the United States and who will not require sponsorship now or in the future. Please note student visas, CPT, OPT, H-1B, TN, and other temporary work authorizations are considered restricted forms of employment eligibility. Once these expire, the candidate must be able to present another valid form of work authorization.
The Role.

Shared Business Technology 


As a data compensation intern, you will Analyze data from multiple sources to surface patterns, anomalies, and opportunity areas and translate those findings into clear recommendations. Contribute to the design or refinement of dashboards, metrics frameworks, or reporting tools that teams actually use. Participate in discovery conversations and working sessions with business unit stakeholders preparing materials, capturing insights, and helping synthesize what you hear. Conduct structured research on industry practices, competitor data strategies, and market benchmarks relevant to our business unit partners 

Love your work.
<ul>
<li>Exposure to how enterprise data functions are designed, operated, and</li>
<li>Hands-on experience with AI tools and agentic systems in active enterprise use</li>
<li>A professional network inside a global advisory and solutions company</li>
<li>Mentorship from an array of leaders with deep expertise in data strategy, architecture and Governance</li></ul> 

</div>
<h2 class="jobSectionHeader">Qualifications</h2>
<div>
Role Requirements:
<div>
<ul><li>Enrolled in a bachelor&rsquo;s degree program with a target graduation date of May 2027</li>
<li>Eligible candidates must be going into their senior year in Fall 2026</li>
<li>Minimum GPA of 3.0 and above</li>
<li>Currently pursuing an undergraduate degree in Data Science, Business Analytics, Information Systems, Computer Science, Business, Economics, or a related field</li>
<li>Comfortable working with data proficient in Excel or Google Sheets; familiarity with SQL, Python, or a BI tool (Power BI, Tableau) is a plus</li>
<li>Strong written communication skills</li>
<li>Curiosity about AI and its application in enterprise contexts</li>
<li>Organized, self-directed, and comfortable navigating ambiguity in a remote environment</li>
<li>Ability to work independently while communicating proactively</li>
<li>Prior internship or project experience involving data analysis or business intelligence work</li>
<li>Exposure to large language models, AI tools, or agentic AI concepts</li>
<li>Experience presenting findings or recommendations to an audience (class presentations count)</li>
<li>Familiarity with the insurance, financial services, or professional services industry</li>
<li>
Able to work legally in the United States indefinitely and without Visa sponsorship</li></ul> 
 
The Application-Interview Process:

Step 1: Online application, including resume/CV

Step 2: Online assessments and Video Interview

Step 3: Virtual Interview with hiring manager and team

Step 4: Offer and onboarding 


Compensation and Benefits 


Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that base salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role and potential for revenue generation (Producer roles only). 


Compensation: The hourly rate being offered for this role is $22-$25/hr USD. 


This role is also eligible for over-time. 


Company Benefits

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):
<ul><li>
Retirement Benefits: Contributory Pension Plan and Savings Plan (401k).
</li></ul>WTW Work Flex:

At WTW, we trust you to know your work and the people, tools, and environment you need to be successful. The majority of our colleagues work in a &ldquo;hybrid&rdquo; style, with a mix of remote, in-person and in-office interactions dependent on the needs of the team, role and clients. Our flexibility is rooted in trust and &ldquo;hybrid&rdquo; is not a one-size-fits-all solution. Visit our career site for more information: https://careers.wtwco.com/wtw-work-flex/. 
 
Recruiting tips: WTW specializes in preparing for the unknown. Here&rsquo;s how to get ready for the big day: https://careers.wtwco.com/hints-and-tips/. 
 
Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles County Fair Chance Ordinance for Employers, we will consider for employment qualified applicants with arrest and conviction records. 
 
We&rsquo;re committed to equal employment opportunity and provide application, interview and workplace adjustments and accommodations to all applicants. If you foresee any barriers, from the application process through to joining WTW, please email candidate.helpdesk@willistowerswatson.com. 
 
This position will remain posted for a minimum of three business days from the date posted or until sufficient/appropriate candidate slate has been identified 
 
EOE, including disability/vets</div></div></div>

Early Careers: Data Internship - Summer 2026

Rush Street Interactive

<div><div>Rush Street Interactive (NYSE: RSI) is a market leader in online casino and sports betting, currently operating real-money gaming with our brands: BetRivers.com, PlaySugarHouse.com, and RushBet.co. We're building bridges between online, social and land-based gaming businesses to create amazing, integrated experiences that keep players in the game.</div>
We are seeking an Accounting Operations Analyst to join our growing accounting team. This role blends traditional accounting responsibilities with a strong focus on innovation, process improvement, and automation. The ideal candidate will contribute to core month-end close activities while also helping improve accounting workflows through technology, data analysis, and AI-driven solutions.

What You'll Do:
<ul>
<li>Support month-end close processes, including preparation of journal entries, reconciliations, and variance analyses</li>
<li>Develop a strong understanding of transaction flows and ensure accounting treatment aligns with US GAAP</li>
<li>Focus on key financial areas such as revenue and cost of revenue within gaming operations</li>
<li>Identify, design, and implement process improvements and automation opportunities within the accounting function</li>
<li>Leverage tools such as Excel, Alteryx, and AI-driven solutions to streamline workflows</li>
<li>Analyze datasets to identify trends, anomalies, and actionable insights</li>
<li>Partner with cross-functional teams to strengthen financial data, streamline reporting, and drive operational efficiency</li>
<li>Communicate findings, recommendations, and process improvements clearly to stakeholders</li>
</ul>
What You'll Bring:
<ul>
<li>Bachelor's degree in Accounting or related field required</li>
<li>1+ years of relevant professional experience, ideally in accounting or finance. Casino industry experience is a plus!</li>
<li>Strong understanding of accounting principles, including US GAAP and journal entry preparation</li>
<li>Ability to understand and follow end-to-end transaction flows</li>
<li>Advanced Excel skills, including data analysis and manipulation</li>
<li>Demonstrated interest in automation, AI, and workflow optimization</li>
<li>Experience or familiarity with automation tools (e.g., Alteryx) preferred</li>
<li>Exposure to building or leveraging AI tools or agents is a strong plus</li>
<li>Strong analytical skills with the ability to assess data and translate findings into meaningful business insights</li>
<li>Effective communication skills, with the ability to engage confidently in cross-functional discussions #LI-REMOTE</li>
</ul><div><div>What Makes Us Great:</div>
<ul><li>Comprehensive compensation</li>
<li>Work-life balance initiatives</li>
<li>Autonomy &ndash; we embrace personal freedom and responsibility</li>
<li>Creativity &ndash; we are open to new ideas of how we can be better</li>
<li>Growth &ndash; we want you to develop personally as well as professionally</li>
<li>Top-notch professionals who are passionate about what they do</li>
<li>People-oriented environment and supportive atmosphere</li>
</ul>
As a rapidly growing company in an emerging industry, you'll have a huge impact on our product and our company. We like proactive team members and strive to have a company of self-disciplined professionals who enjoy collaboration, having fun, and of course, achieving together what others believe to be improbable. We are dedicated to treating everyone with respect and to support your professional and personal growth.

Rush Street Interactive is an equal opportunity employer and committed to a diverse and inclusive workplace. All qualified applicants will be considered for employment without regard to race, national origin, ancestry, sex, sexual orientation, sexual identity and expression, marital status, family status, lifestyle, age, culture, religion, military and veteran status, citizenship, or disability.

Be at the forefront of this ground-breaking industry! Apply now!

Rush Street Interactive uses AI-assisted tools at select stages of the hiring process to enhance efficiency, consistency, and communication. AI does not make hiring decisions - final decisions are made exclusively by our recruiting and hiring teams.</div></div>

Accounting Operations Analyst

Alignerr

<div>
 
 About The Role
 
 
 
 We're looking for experienced entrepreneurship educators and business experts to help shape how AI understands startups, innovation, and business planning. Your real-world knowledge will directly improve the quality and accuracy of AI systems used by learners, founders, and business professionals worldwide.
 
 
 <ul>
 <li>
 Organization: Alignerr (Powered by Labelbox)
 </li>
 <li>
 Type: Hourly Contract
 </li>
 <li>
 Location: Remote
 </li>
 <li>
 Commitment: 10&ndash;40 hours/week
 
 
 </li>
 </ul>
 
 What You'll Do
 
 
 
 <ul>
 <li>
 Review AI-generated startup and entrepreneurship scenarios for accuracy and real-world relevance
 </li>
 <li>
 Evaluate business models, assumptions, and go-to-market strategies against practical standards
 </li>
 <li>
 Identify unrealistic financial projections, flawed logic, or misleading advice
 </li>
 <li>
 Provide structured, expert feedback to improve the quality of AI training content
 </li>
 <li>
 Work independently and asynchronously &mdash; on a schedule that fits your life
 
 
 </li>
 </ul>
 
 Who You Are
 
 
 
 <ul>
 <li>
 3+ years of experience teaching entrepreneurship, small business, or startup strategy
 </li>
 <li>
 Strong working knowledge of business models, early-stage decision-making, and venture economics
 </li>
 <li>
 Able to critically evaluate written business plans and identify weaknesses with confidence
 </li>
 <li>
 Comfortable providing practical, applied feedback grounded in real business experience
 </li>
 <li>
 Self-motivated and reliable when working independently
 
 
 </li>
 </ul>
 
 Nice to Have
 
 
 
 <ul>
 <li>
 MBA or graduate degree with an entrepreneurship focus
 </li>
 <li>
 Experience as a founder, operator, or startup advisor
 </li>
 <li>
 Familiarity with AI systems or content evaluation workflows
 
 
 </li>
 </ul>
 
 Why Join Us
 
 
 
 <ul>
 <li>
 Work on cutting-edge AI projects with top research labs
 </li>
 <li>
 Fully remote and flexible &mdash; work on your own schedule
 </li>
 <li>
 Freelance perks: autonomy, variety, and global collaboration
 </li>
 <li>
 Contribute to meaningful work that shapes how AI teaches and advises the next generation of entrepreneurs
 </li>
 <li>
 Potential for ongoing work and contract extension
 </li>
 </ul>
</div>

Entrepreneurship Instructor (AI Training)

Explore 496+ Ai trainer data annotator remote in Chicago this May. Find roles across top companies and apply now to boost your career.