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Bookkeeper (Part Time, 1099)

| Chicago

Why our work matters

The healthcare industry is notoriously difficult to navigate. One third of the over $3 trillion spent on healthcare annually results from this complexity, and more than half of Americans don’t get care because of the price tag. Our mission is to simplify the healthcare experience in a way that provides access to better care at a lower cost.

Since 2014, HealthJoy has been committed to revolutionizing the way people access healthcare. Through an easy to use app that brings together healthcare information and on-demand help, we enable people to be more informed and confident when making decisions about their healthcare. It’s no small feat, but our work makes a significant difference in people’s lives.

Our team has compassion and energy for the problems we are solving. We hold ourselves accountable and deliver on ambitious, meaningful goals. Putting egos aside, we commit to doing what it takes to bring positive changes to our users. Everyone plays a role.

Together we are building the future of healthcare. Join us!

Your role in our mission

As HealthJoy’s Bookkeeper, you will work closely with our Vice President of Finance and Controller to build out accounting processes and controls. This role will have a high level of responsibility and the ability to make an immediate impact at a growing company. The role will have ownership of HealthJoy’s billing, receivables, and payables functions.

How you’ll contribute

  • Review invoicing/ billing for completeness and accuracy; resolving billing issues when necessary and paying bills on behalf of HealthJoy.
  • Scan paper checks and record payments in Bill.com on a weekly basis
  • Record all customer transactions into QB; including checks, deposits, Stripe billings/ invoices, credit memos, discounts, trials and other transactions affecting the checking account.
  • Review new subscription contracts and ensure they are set up correctly in QBO (or AR sub-ledger like Stripe); confirming data agrees with Salesforce CRM/ sales reports for accurate revenue recognition and deferred revenue reporting in QBO.
  • Review AR Aging reports and identify collection issues for resolution, e.g. Dunning on failed credit card charges.
  • Own bi-monthly payroll cycle; on-boarding new employees and adjusting current employee compensation and withholdings as needed
  • Ensure taxes due are paid on time and quarterly and annual filings are completed on time.
  • Record adjusting journal entries such as accruals and depreciation.
  • Reconcile all balance sheet accounts; includes bank reconciliation for the checking, savings, credit card and loan accounts and any other related key accounts.

Your background

  • QuickBooks Online (QBO) experience required
  • Bill.com (BDC) experience preferred
  • Flexibility to work up to 30 hours per week once a month (first week of the month in order to close the books)
  • Detail-oriented and highly organized
  • Ability to work independently towards weekly and monthly deadlines
  • Integrity and understanding of confidentiality
  • Minimum 2+ years of experience as a Bookkeeper or Administrative Assistant

Note: The position is a 1099 contract, part-time (20-30 hours per week) role based out of our River North office.

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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • JavaLanguages
    • JavascriptLanguages
    • KotlinLanguages
    • PythonLanguages
    • RLanguages
    • SqlLanguages
    • SwiftLanguages
    • ReactLibraries
    • ReduxLibraries
    • AngularJSFrameworks
    • FlaskFrameworks
    • HadoopFrameworks
    • TensorFlowFrameworks
    • Google AnalyticsAnalytics
    • MixpanelAnalytics
    • BalsamiqDesign
    • IllustratorDesign
    • PhotoshopDesign
    • SketchDesign
    • ConfluenceManagement
    • JIRAManagement
    • WordpressCMS
    • SalesforceCRM
    • MailChimpEmail
    • SendGridEmail
    • customer.ioEmail
    • PardotLead Gen
    • ZapierLead Gen


We're in River North, a fashionable neighborhood that has plenty of shops, restaurants (inexpensive to gourmet) and bars. Subway access within steps.

An Insider's view of HealthJoy

What's something quirky about your company?

HealthJoy was started in a house in River North that's blocks from our existing office. At one time, we had over 25 employees stuffed in that house. The co-founders lived in the 4th floor and would occasionally cook lunch for the team.



What's the biggest problem your team is solving?

As everyone knows, healthcare is overly complicated. People get these amazing health plans but are almost scared to use them. We are trying to make using healthcare as easy as possible. It's like you have an industry insider always accessible right from your mobile phone.


Director of Product Analysis

How does the company support your career growth?

One of my favorite parts about working at a startup is that there is no playbook-we’re creating new products, processes, and client experiences every day. Our corporate culture values individuals who come to the table with fresh ideas, and we empower team members with the autonomy and resources to execute when there’s a better way of doing things.


Director of Customer Success

What is your vision for the company?

Our vision is to be America’s best healthcare and benefits guidance platform. We want to build an app where people can come anytime to understand, treat and save on their healthcare and benefits. We want to make the whole experience as simple as possible.


President and Co-Founder

What projects are you most excited about?

Bringing artificial intelligence to employee benefits is changing the game. The potential use cases for robust and efficient AI algorithms are enormous and can have a dramatic impact on how people get care. We have a three-year roadmap that's planned, some very exciting stuff.


CEO and Founder

What are HealthJoy Perks + Benefits

HealthJoy Benefits Overview

At HealthJoy, we take care of our people so they can take care of others. We offer a wide range of competitive benefits in areas including health, finance, convenience, time-off, and relocation. We work hard to foster a diverse, supportive and welcoming workplace in a casual environment. We also like to have fun!

Eat lunch together
Open Door Policy
Group Brainstorming Sessions
Open Office Floor Plan
Documented Equal Pay Policy
Health Insurance & Wellness Benefits
Disability Insurance
Health Insurance Benefits
Life Insurance
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Flexible Work Schedule
Remote Work Program
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Perks & Discounts
Casual Dress
Stocked Kitchen
Some Meals Provided
Happy Hours
Professional Development Benefits
Promote From Within
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