Keeper Tax: Great Communicator to Demystify US Taxes for Freelancers

Headquarters: San Francisco, CA


We’re 💸 Keeper Tax 

We’re a bookkeeping business that finds tax write-offs for our self-employed customers. 
With the rise of gig work platforms and side hustle culture, over half of Gen Z workers are now getting paid with 1099 contracts. They might not think of themselves as business owners, but they are expected to file business taxes. This can feel incredibly daunting and frustrating, and Bookkeepers at Keeper Tax help them navigate these complexities. 
Tax-related content on the internet today is awful – full of jargon and overly conservative.  In contrast, we’re not the traditional stuffy accounting firm. It’ll be your mission to de-mystify and detangle the tax mess that the IRS created.  Bookkeepers provide clear tax guidance that’s easy to read, jargon-free, helps save money, and is relatable to Gen Z. 
We’re looking for someone who will love helping self-employed people find tax write-offs. If you’d love interacting with people daily to help them learn how to save money, then read on… 

About You 😁

  • You’re highly skilled at solving customer service questions where you must research the answer yourself first. We’re looking for at least 1-2 years of experience in roles where you had to look up and interpret information to answer customers’ questions.
  • You’re empathetic to customers and can easily put yourself in their shoes. You realize that not everyone has the same skill set and that smart people sometimes make mistakes. You make customers feel empowered after interacting with support and not stupid because of a small mistake.
  • You obsess over the details. Maybe you have a one emoticon and one exclamation point rule of thumb for every interaction. Maybe it’s only two sentences per message. Either way, you make sure each word, each punctuation mark, and each emoji makes the customer delighted to work with you. 
  • You love finding solutions to problems. Every customer is different, many times radically so. You relish being able to meet their specific needs and finding write-offs that may have gone unnoticed without you. 
  • You love to write.  Almost everything is we do is done via written communication (both with customers and between teammates).  Succinctness, grammar, and spelling matter a lot.  Your writing is also approachable and fun — this isn’t the tax company your parents use. 
  • You’re persistent.  Many times, answering questions will involve researching tax information. You love the opportunity to solve new problems every day and won’t give up when you don’t know the answer right away. 
  • You’re also likely to use our product because you’re also a freelancer.  You often use apps, software, and technology in your life to improve it.  You’re also not afraid to be authentic in your messages and use heaps of slang and emojis 🤩 (but you keep it professional). 
  • You don’t have to be a tax expert. We help train you on the basics on paid time.

What’s a Bookkeeper’s Day like? 🤔

  • Help customers via our system to ensure they have the best experience possible, adjust their write-offs, and answer their questions.
  • You’ll have help to answer the more difficult questions after you’ve exhausted your resources. Willing to learn fundamental individual US tax law – we will teach you on paid time. It’s pretty straightforward. 
  • Use our platform to learn the product and gain knowledge to help customers.  Use it for real throughout the year and file your taxes with us if you want — we’ll make it free for you. 
  • Maintain accuracy and efficiency standards for a Bookkeeper at Keeper Tax.
  • You will be handling private financial data, so we’ll need you to sign non-disclosure agreements upfront. 

Work Hours 😎

  • Willing to work at least five days a week for 5-8 hours a day.
  • You can choose when to work between the hours of 7 am-10 pm EST.
  • We need folks that are flexible to work weekdays and weekends. 
  • The initial contract will be for about 2 hours a day for two weeks, and then we can re-assess after that. 

How to Apply for this Job 📝

We want you to be comfortable and excited while applying for this job because it’s often not the case when you put yourself out there. The hiring process feels like a black box.  You apply, wait weeks and weeks and never hear back.  You’re left wondering why you wasted your time in the first place – reinforcing self-doubt and creating imposter syndrome.  It takes guts to apply to any new role, and often your only reward is silence. 
We’re different at Keeper Tax.  We want you to know that you will hear back from us when you apply for this role, even if we think we’re not a good fit for each other.  
To be completely transparent, this is what happens in the process: 
  1. Applying – when you apply, we’ll get notified you took the time to respond, and we’ll take the time to review each application manually — no robots. 
  2. Evaluation – We’ll evaluate each application for communication skills, grammar, and evidence that demonstrates you have the qualifications listed in the About You section of the job post. 
  3. Interview – Once past the evaluation, an applicant is invited to interview.  This is done over google meet, and the applicant should join from a PC capable of sharing their screen.  During the interview, we’ll jump into some actual hands-on activities.  This is intended to see if you’ll like the role and if you have the skills required.  You won’t be asked questions that don’t matter.  For example, we won’t ask you if you know how many balloons fit inside a Toyota Corolla or what the airspeed velocity of an unladen swallow is. 
  4. Final Decision – After the interview, we’ll evaluate each candidate and decide who to offer Trial Periods.
  5. Trial Period – For about one to two weeks, you’ll work limited paid hours as a 1099 contractor while we review how you interact with customers.  It’s usually 2-3 hours a day.  
  6. Bookkeeper period – After the trial period, you’ll be considered a fully-fledged Bookkeeper at Keeper Tax! 

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