2

Entry Level 1099 Jobs in Wisconsin (NOW HIRING)

Accounting Intern (Spring 2027)

Brookfield, WI · On-site

$15 - $19/hr

Work performed is similar to the activities of an entry-level staff accountant, and interns are ... Prepare tax return extensions * Assist in the preparation of Form 1099 informational returns for ...

This is an entry-level, learn-the-business role designed for someone who is motivated, curious, and ... About the structure of the role This is a 1099, commission-based position designed as a long-term ...

Entry Level 1099 information

What are the key skills and qualifications needed to thrive as an entry level 1099 contractor?

To succeed as an Entry Level 1099 contractor, you generally need strong self-management skills, basic industry knowledge, and the ability to work independently, often without direct supervision. Familiarity with invoicing software, time-tracking tools, and basic accounting systems is typically expected to manage your freelance business. Exceptional communication, adaptability, and organizational skills help you build client relationships and handle multiple projects efficiently. These skills and qualities are important because they enable you to deliver quality work, maintain client satisfaction, and ensure reliable income as an independent contractor.

What are some common challenges faced by entry level 1099 workers, and how can they be addressed?

Entry Level 1099 workers, also known as independent contractors, often face challenges such as managing inconsistent income, handling self-employment taxes, and securing their own benefits like health insurance. To address these, it's important to budget carefully, set aside money for taxes throughout the year, and research affordable health coverage options. Additionally, building strong relationships with clients and maintaining a professional network can help ensure a steady flow of work and provide support as you develop your career.

What is the difference between Entry Level 1099 vs Entry Level W-2?

AspectEntry Level 1099Entry Level W-2
Tax StatusIndependent contractor, responsible for own taxesEmployee, taxes withheld by employer
Work EnvironmentTypically freelance or contract-basedFull-time or part-time employment
CredentialsUsually minimal; depends on industryOften requires onboarding and HR paperwork
Employer UsageUsed by companies for project-based workUsed for regular employment roles

Entry Level 1099 workers operate as independent contractors, handling their own taxes and often working on a freelance basis. In contrast, Entry Level W-2 employees are hired as regular staff, with taxes withheld by the employer. The choice impacts tax responsibilities, work environment, and employer relationships, making it important to understand these differences when seeking entry-level opportunities.

What is an entry level 1099?

Entry Level 1099 jobs are positions where individuals are hired as independent contractors rather than traditional employees, typically with little to no prior experience required. The term '1099' refers to the IRS form used to report income earned by independent contractors. In these roles, workers are responsible for managing their own taxes, benefits, and work expenses. Entry level 1099 jobs can be found in fields like sales, gig work, consulting, and freelance services, offering flexibility but less job security and fewer benefits than standard employment.
What are the most commonly searched types of 1099 jobs in Wisconsin? The most popular types of 1099 jobs in Wisconsin are:
What are popular job titles related to Entry Level 1099 jobs in Wisconsin? For Entry Level 1099 jobs in Wisconsin, the most frequently searched job titles are:
What cities in Wisconsin are hiring for Entry Level 1099 jobs? Cities in Wisconsin with the most Entry Level 1099 job openings:
Infographic showing various Entry Level 1099 job openings in Wisconsin as of August 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 33% In-person, and 67% Remote job distribution.

Tax and Accounting Assistant

Compeer Financial

Dodgeville, WI • Hybrid

Other

Posted 6 days ago


Compeer Financial rating

9.1

Company rating: 9.1 out of 10

Based on 6 frontline employees who took The Breakroom Quiz


Job description

Where you will work: This position offers a hybrid schedule with 1 to 2 remote days per week, based primarily in the Dodgeville, WI office.

The contributions you will make: This position assists Tax and Accounting with operational tasks that provide clients with information for credit, accounting, tax, and management decisions.

A typical day: 

Tax Support 

  • Processes W-2's, 1099's, eFile and Coalation.
  • Keys, processes, prints and mails customer W-2's and 1099 forms.
  • Schedules tax planning and preparation appointments, as requested.
  • Ensures tax service fees are uploaded into the Related Services System (RSS).
  • Assigns CIF numbers and sets up new member records.
  • Updates tax database as necessary.
  • Completes various tax mailings including large mass mailings for tax planning and year end as necessary.
  • Works with the credit department to produce and process Consent to Disclosures forms.
  • Inputs basic tax return information into system for Tax Consultants.

Client Service and Support

  • Provides accurate and timely accounting and tax processing support.
  • Maintains tracking system and adheres to department policies, procedures and best practices to balance the workload and meet aggressive timeliness.
  • Maintains a working knowledge of tax and accounting products and services to the extent that customer calls or questions can be directed to the appropriate tax consultant or accounting specialist.
  • Identifies and suggests improvements to work process, policies, procedures and best practices.
  • Serves as a resource for other departments regarding tax and accounting products and services.

Accounting Support 

  • Provides accurate and timely accounting processing support.
  • Keys less complex accounting activities (depreciation, payroll and full-services accounts) into appropriate accounting software.
  • Enters, reviews, balances, prints, assembles and mails reports to users.

The skills and experience we prefer you have: 

  • High School Diploma or equivalent required; Associate degree in business administration, accounting or related field preferred.
  • Entry-level experience in accounting or tax in a financial institution.
  • Strong listening, written and verbal communication skills, with ability to communicate at all levels of the organization.
  • Skill in developing and maintaining interpersonal relationships.
  • High degree of accuracy, attention to detail, organizational and time management skills.
  • Strong problem solving, decision making and organizational skills.
  • Strong computer skills, including MS Office applications and customer relationship management (CRM) programs.
  • Strong analytical skills with attention to detail.

How we will take care of you:

Our job titles may span more than one career level (associate, senior, principal, etc.). The actual title and base pay offered is dependent upon many factors, such as: training, transferable skills, work experience, business needs and market demands. The base pay range is subject to change and may be modified in the future. This role is eligible for variable compensation and other benefits.


What Compeer Financial employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom