Welcome to DataAnnotation! We pay smart folks to train AI. We offer a remote, flexible work model- you choose your own hours and get to work when you want, whenever you want. Apply now through our open Job Listings.

Industry: Software Development
Company Size: 5,001-10,000 employees

DataAnnotation

Savvy Admin PROD

DataAnnotation is committed to creating high-quality AI. We are looking for an M&A Analyst to join our team to help train the next generation of AI while enjoying the flexibility of remote work and the freedom to set your own schedule. This role is designed to fit a variety of lifestyles — whether you’re looking to contribute part-time alongside a current position, pursue it full-time, or engage periodically as a flexible professional opportunity.

We're currently expanding into an exciting new area – teaching AI Assistant models to be a more useful tool for finance professionals. We're seeking experienced finance professionals with advanced degrees (MBA+) and professional experience to use their expertise to help shape how AI understands financial principles and decision-making.

**Role**

We’re growing a team of finance experts, and as the team grows, so will your opportunities. In this role, you might:

- Review and improve AI Assistant answers to questions about macro trends, corporate finance, and capital markets

- Leverage your education and work experience to check the reasoning and accuracy of an AI Assistant's work

- Push the models with complex, real-world scenarios and edge cases to see where their reasoning holds up – and where it doesn’t.

- Share clear, structured feedback to help make each new version of the AI smarter and more reliable.

To succeed in this position, you should have expert-level financial reasoning and formal training in a finance-related discipline. A Master’s or PhD (completed or in progress) is strongly preferred. Relevant backgrounds include Financial Accounting, Investment Banking, Corporate Development, Wealth Management, and Insurance Planning.

**Benefits**

- This is a full-time or part-time REMOTE position

- You’ll be able to choose which projects you want to work on

- You can work on your own schedule

- Projects are paid hourly starting at USD $50-$60 per hour, with bonuses on high-quality and high-volume work

**Responsibilities**

- Give AI chatbots diverse and complex problems and evaluate their outputs

- Evaluate the quality produced by AI models for correctness and performance

**Qualifications**

- Fluency in English (native or bilingual level)

- Detail-oriented

- Proficient in financial analysis, financial modeling, data analysis, and other reasoning exercises related to finance management

- A current, in progress, or completed Masters and/or PhD is is preferred but not required

Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any currency conversions from USD. Only applicants in the United States will be considered for this role. This is an independent contract position.

#finance

M&A Analyst

DataAnnotation is committed to creating high-quality AI. We are looking for a CIO to join

our team to help train the next generation of AI while enjoying the flexibility of remote work and the

freedom to set your own schedule. This role is designed to fit a variety of lifestyles — whether you’re

looking to contribute part-time alongside a current position, pursue it full-time, or engage periodically as

a flexible professional opportunity.

We're currently expanding into an exciting new area – teaching AI Assistant models to be a more useful

tool for finance professionals. We're seeking experienced finance professionals with advanced degrees

(MBA+) and professional experience to use their expertise to help shape how AI understands financial

principles and decision-making.

We’re growing a team of finance experts, and as the team grows, so will your opportunities. In this role,

**You Might**

- Review and improve AI Assistant answers to questions about macro trends, corporate finance,

and capital markets

- Leverage your education and work experience to check the reasoning and accuracy of an AI

Assistant's work

- Push the models with complex, real-world scenarios and edge cases to see where their

reasoning holds up – and where it doesn’t.

- Share clear, structured feedback to help make each new version of the AI smarter and more

reliable.

To succeed in this position, you should have expert-level financial reasoning and formal training in a

finance-related discipline. A Master’s or PhD (completed or in progress) is strongly preferred. Relevant

backgrounds include Financial Accounting, Investment Banking, Corporate Development, Wealth

Management, and Insurance Planning.

**Benefits**

- This is a full-time or part-time REMOTE position

- You’ll be able to choose which projects you want to work on

- You can work on your own schedule

- Projects are paid hourly starting at USD $50-$60 per hour, with bonuses on high-quality and

high-volume work

**Responsibilities**

- Give AI chatbots diverse and complex problems and evaluate their outputs

- Evaluate the quality produced by AI models for correctness and performance

**Qualifications**

- Fluency in English (native or bilingual level)

- Detail-oriented

- Proficient in financial analysis, financial modeling, data analysis, and other reasoning exercises

related to finance management

- A current, in progress, or completed Masters and/or PhD is preferred but not required

Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any

currency conversions from USD. Only applicants in the United States will be considered for this role. This is an independent contract position.

#finance

Chief Information Officer

DataAnnotation is committed to creating high-quality AI. We are looking for a VC Associate to join our team to help train the next generation of AI while enjoying the flexibility of remote work and the freedom to set your own schedule. This role is designed to fit a variety of lifestyles — whether you’re looking to contribute part-time alongside a current position, pursue it full-time, or engage periodically as a flexible professional opportunity.

We're currently expanding into an exciting new area – teaching AI Assistant models to be a more useful tool for finance professionals. We're seeking experienced finance professionals with advanced degrees (MBA+) and professional experience to use their expertise to help shape how AI understands financial principles and decision-making.

**Role**

We’re growing a team of finance experts, and as the team grows, so will your opportunities. In this role, you might:

- Review and improve AI Assistant answers to questions about macro trends, corporate finance, and capital markets

- Leverage your education and work experience to check the reasoning and accuracy of an AI Assistant's work

- Push the models with complex, real-world scenarios and edge cases to see where their reasoning holds up – and where it doesn’t.

- Share clear, structured feedback to help make each new version of the AI smarter and more reliable.

To succeed in this position, you should have expert-level financial reasoning and formal training in a finance-related discipline. A Master’s or PhD (completed or in progress) is strongly preferred. Relevant backgrounds include Financial Accounting, Investment Banking, Corporate Development, Wealth Management, and Insurance Planning.

**Benefits**

- This is a full-time or part-time REMOTE position

- You’ll be able to choose which projects you want to work on

- You can work on your own schedule

- Projects are paid hourly starting at USD $50-$60 per hour, with bonuses on high-quality and high-volume work

**Responsibilities**

- Give AI chatbots diverse and complex problems and evaluate their outputs

- Evaluate the quality produced by AI models for correctness and performance

**Qualifications**

- Fluency in English (native or bilingual level)

- Detail-oriented

- Proficient in financial analysis, financial modeling, data analysis, and other reasoning exercises related to finance management

- A current, in progress, or completed Masters and/or PhD is is preferred but not required

Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any currency conversions from USD. Only applicants in the United States will be considered for this role. This is an independent contract position.

#finance

VC Associate

Ascend Learning is one company with a powerful portfolio of brands rooted in purpose with a clear mission: to help change lives by providing software-based, data-driven educational support that accelerates learning, advances job readiness and enables employment success. We're committed to accelerating the learning pathways that can move people into careers where they have the knowledge and skills to have an impact and help change lives in the communities they serve.

As a tech-enabled services company and national leader in developing and delivering online educational content, software, assessments, analytics and simulations serving students, educational institutions and employers, we focus on high-growth careers in a range of industries, with a special focus on healthcare and other high-growth, licensure-driven professions. 

Our brands are organized into three segments: healthcare, fitness and wellness, and safety and security. We help frontline healthcare workers, nurses, physicians, emergency medical professionals, personal and group fitness trainers, financial advisors, insurance brokers and cybersecurity and skilled trades professionals prepare for licensure and certification — people who make our communities healthier, safer and stronger. 

Headquartered in Burlington, MA with additional office locations and hybrid and remote workers in cities across the U.S., Ascend Learning was recognized by Newsweek and Plant-A Insights Group as one of America's 2023 Greatest Workplaces for Diversity.

Industry: E-learning
Company Size: 1,001-5,000 employees

Ascend Learning

**We Impact Lives Through Purpose-Driven Work in A People First Culture**

Ascend Learning, a leading healthcare and learning technology company, is the connection between a powerful portfolio of brands serving students, educators, and employers with outcomes-based, data-driven solutions across the lifecycle of learning. From testing to certification, Ascend Learning products are used by physicians, emergency medical professionals, nurses, allied health professionals, certified personal trainers, financial advisors, skilled trades professionals and insurance brokers.

Headquartered in Burlington, MA, with additional office locations and hybrid and remote workers in cities across the U.S., Ascend Learning was recognized by Newsweek and Plant-A Insights Group as one of America’s 2025 Greatest Workplaces as well as America’s Best Places to work for Mental Well-Being for 2025.

We're always looking for talented, passionate professionals to join us in our mission to help change lives. If this sounds like an environment where you'd thrive, read on to learn more.

**What You'll Do**

Ascend Learning is hiring now for a Travel and Expense Specialist (T&E). As a Travel and Expense (T&E) Specialist you will be responsible for managing end-to-end T&E operations for over 2,500 team members. The role administers the corporate credit card program while ensuring accurate, compliant expense reconciliation and timely reimbursements using our expense management tool, Medius Expensya. This position also supports vendor master data maintenance within the ERP system and serves as backup to the AP team.

**WHERE YOU’LL WORK**

This position will work a hybrid schedule from our Leawood, KS office location.

**How You’ll Spend Your Time**

-  Review and audit employee expense reports for accuracy, proper documentation, and compliance with travel and corporate credit card policies, ensuring timely reimbursement.

-  Administer the corporate credit card program, including issuing new cards, closing accounts, monitoring activity, and reconciling delinquent accounts.

-  Maintain and support the expense management system, including user setup, terminations, and access permissions.

-  Provide training and ongoing support to employees and promptly respond to inquiries through shared mailboxes with a strong customer service focus.

-  Generate and analyze expense reports to identify trends and monitor compliance.

-  Process supplier additions and updates in the ERP system, including validating W9 forms.

-  Support internal and external audits by preparing and providing documentation.

-  Assist in developing, documenting, and maintaining travel and expense policies.

-  Respond to ad hoc reporting requests and participate in special projects.

**What You'll Need**

-  Minimum of 2+ years of Travel & Expense (T&E) administration experience required.

-  Experience in Accounts Payable, general accounting, and customer service preferred.

-  Proficient in expense management systems (Concur, Expensya) and large ERP platforms.

-  Advanced Microsoft Excel skills and strong overall proficiency in Microsoft Office.

-  Solid understanding of expense reporting, auditing, and financial controls.

-  Excellent interpersonal, written, and verbal communication skills to interact with employees and external vendors.

-  Strong analytical, problem-solving, and critical thinking abilities with high attention to detail.

-  Highly organized, self-directed, and able to manage multiple priorities in a fast-paced environment.

-  Demonstrated ability to take initiative and expand responsibilities over time.

-  Commitment to accuracy, integrity, and accountability.

-  Associate’s degree and/or bachelor’s degree preferred. High School diploma or GED required.

**Benefits**

-  Flexible and generous paid time off

-  Competitive medical, dental, vision and life insurance

-  401(k) employer matching program

-  Parental leave

-  Wellness resources

-  Charitable matching program

-  On-site workout facilities (Leawood, Gilbert, Burlington)

-  Community outreach groups

-  Tuition reimbursement

**Fostering A Sense of Belonging**

Our values-driven culture unifies our teams and inspires a mindset of action, innovation, and collaboration, with a relentless focus on customers. We seek out and celebrate all people and perspectives and cultivate an inclusive culture where everyone can thrive, feel valued, and be authentic. Our culture is firmly rooted in the belief that by embracing our differences and drawing on diverse perspectives, we are a stronger, more innovative, and more successful organization where employees experience a sense of belonging.

Ascend Learning, LLC is proud to be an equal opportunity employer (M/F/Vets/Disabled). No agency or search firm submissions will be accepted. Applications for U.S.-based positions with Ascend Learning, LLC must be legally authorized to work in the United States, and verification of employment eligibility will be required at the time of hire.

Travel & Expense Specialist

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