Paying independent contractors: How Hubstaff saves $32,400 with a simple system

Paying independent contractors: How Hubstaff saves $32,400 with a simple system

At Hubstaff, we have a team of 16 contractors (excluding founders) spread all over the world. This post will detail the simplest and most cost effective methods we’ve found to pay them. I’ve been running remote teams for 12 years (as of 2015) and I hate paying unnecessary fees, so I always look for innovative ways to send more money to the bottom line. We’re currently moving approximately $32,400 to our bottom line with ingenious methods.

If you don’t have time to read the full post, here’s the gist of it; I discovered PayPal Mass Payments about 5 years ago and have used it ever since. This online payroll solution balances cost effectiveness with ease of use.

PayPal Mass Payments balances cost effectiveness with ease of use. Click To Tweet

Below is how we use it to pay our virtual team for less than $200 monthly, which we could reduce to less than $60 if we paid once a month instead of once a week. To top it off, all of our payroll processes are fully automated so we don’t waste any time with low-level admin work.

Masspay is not the simplest solution, but it’s not too hard either. It’s worthwhile because of their convenience and affordable pricing, which is what won our bootstrapped startup over. As the screenshot below shows, although growing rapidly, we’re still a small company that needs to find and use the most efficient and affordable solutions.

Our Payment Philosophy

We have a few principles that we follow when hiring and arranging payments.

  • We pay by the hour
  • We don’t like retainers
  • We pay our team weekly

First Things First: We Pay by the Hour

We pay our team members by the hour at Hubstaff. Almost all of our contractors are on hourly contracts and I believe that the days of fixed cost relationships are slowly coming to an end (more on why we hate retainers in a bit).

Here’s how it breaks down:

  • 14 people are paid automatically via Paypal MassPay – 13 of them are paid by the hour and 1 is paid a fixed rate
  • 2 of them are paid by ACH (Chase) – These contractors invoice much less frequently, and do not track time in Hubstaff.
  • Our team members are in the US (7), Turkey (1), Bulgaria (1), India (2), Philippines (2), Serbia (1), Ukraine (1), Romania (1).

The main reason we pay by the hour is because we don’t want to pay for time that is not spent on our projects. This is the least stressful and most fair arrangement for both parties that we have found. We build relationships with our contractors so they can work when (and where) they want to work, provide them a lot of freedom and simply pay them for their valuable time when they work for us.

We build relationships with our contractors so they can work whenever and wherever they want. Click To Tweet

That being said, when we find someone great, we have a conversation with them and tell them that we’d love for them to transition 100% of their time to Hubstaff work. We generally do this by simply scaling up their work. We never hire someone full-time up front.
Most of our contractors have other clients (usually 1-2 clients in addition to Hubstaff). On average, our team members work around 4 to 5 hours a day for Hubstaff. For our developers we have a slightly different thought process wherein we try to get them to work on our projects full-time in order to capture 100% of their mental activity. This is because in development it’s pretty hard to switch gears from project to project.

If we have a team member that we want to limit to a certain number of hours per week, we use the budgets feature in Hubstaff. Sometimes we do this because we only have a certain amount of cash that we want to allocate to that type of work on a weekly basis. Other times it’s because we just don’t want that person running up a bunch of hours doing work that is not so important to our business at the current time. Those are similar reasons but in general one of them origins from a person, and one origins from a project.

Since our people are mostly paid by the hour and only get paid for the amount of time that is worked, all we have to do is run a simple calculation of hourly rate multiplied by hours worked that week.

We Don’t Pay Retainer Fees

Some contractors like to work on retainer, which is fine with us but we still ask for an hourly rate that corresponds with time tracked in Hubstaff. So for example, if a contractor asks for $2,000 a month and we agree on an hourly rate of $20/hour, we would like to see approximately 100 hours tracked in Hubstaff every month. When we have a setup like this, we set payment frequency for once a month at a fixed rate of $2,000 (we recommend sending payment after the work has been performed). In this scenario we could use PayPal MassPay to transfer money and avoid fees.

The type of contracts we avoid are those wherein a contractor asks for $2,500/month with absolutely no accountability for that money. We’ve seen freelancers try to work for several different clients at once and effectively double their hourly rate because they work for two clients at the same time and collect a retainer. Retainers are awesome for the party collecting the money and really bad for the person sending the money.

Retainers are awesome for the party collecting money and bad for the party sending it. Click To Tweet

I’ve personally lost several thousand dollars because I paid a retainer then never heard back from the contractor. Whenever I have a contractor ask for a retainer up front, I generally run the other direction because I know I’m about to get screwed.

Jack Sparrow Running

We run like hell away from contractors who demand retainers up front

The other thing that sucks about retainers is the feeling that you constantly have to feed work to the contractor. It feels like you have to work extra hard before or after a vacation because once you leave your contractor on retainer is going to continue to get paid even if there’s no work to be done.

We Pay Weekly

We pay weekly because our contractors like it. We’d rather give them money now instead of every other week or monthly. Our work week runs from Monday 12 a.m. to Sunday 11:29 p.m. Once the week ends, Hubstaff’s automatic payroll calculates payroll and sends the funds out so contractors are paid approximately 5 p.m. EST on Monday evening.

I hate chasing money that I’m owed, so we are happy to give our contractors this small reward for working with us. In all my businesses over the years I’ve always paid contractors very quickly, partially because I hate debt myself and things hanging over my head, but also because I feel it’s the right thing to do.

Overview of Payment Options

Option 1: Payment Transfer Services (Paypal, Payoneer, Transferwise)

In my experience, as long as you have an accurate way of calculating the amount you need to transfer to your contractor, this method has been the proven winner for three reasons.

  1. It’s the least expensive.
  2. It’s the best for companies that have international contractors or employees.
  3. It’s fast and reliable.
Payment transfer services are inexpensive, international, fast and reliable. Click To Tweet

Out of the services that we’ve tried, Paypal has stood out as our best fit. However, PayPal has absolutely terrible customer service. It’s horrid. As a general rule, everyone you call at PayPal will give you a different answer. Many times it’s very hard to get someone on the line, they will not take your number down and call you back in case you get disconnected and they don’t have email support or screensharing.

The best way to deal with this is to request an assigned representative. They can usually handle any issues like magic and act like real people, unlike the rest of PayPal support.

All that aside, once you get past their support issues or if you don’t need support, PayPal is awesome because it’s supported in most countries and reliable. It works; your contractors will get their money and they’ll get it fast.

There are a ton of payment service providers in this space. Here’s a list of some options:

*Services marked can integrate with Hubstaff.

In general the biggest differences between these services are the level of technology, countries supported and fees. Over the years, I’ve processed about 10 million dollars through PayPal (I used to have a company that operated solely on Paypal) in both sent and received payments, and I’ve never run into a problem like payments being sent twice or someone not receiving a payment. This track record and reliability is one of the simplest reasons they top my list. That’s the simplest reason why they are the winner for me. It’s also relatively easy to get money in and out of PayPal as long as you have a verified account. For the purposes of this post, I’m going to focus on PayPal with the acknowledgement that there are many other options for you if you can’t or won’t work with PayPal.

There are two main ways to transfer money in PayPal:

1. Paypal MassPay – MassPay is quirky and a pain to get set up on your account. You’ve got to call PayPal and have them turn it on in your account. It’s hard to know if you even have it approved, plus you’ve got to have a business account. Once you finally do get everything set up it’s awesome. Here are some of the ways PayPal MassPay differs from the regular PayPal system.

  • MassPay requires that you have a balance larger than the payment you are trying to process. For us, we transfer around 4,500 a week in PayPal, so we’ve got to maintain a constant balance of around $5,000 USD in Paypal if we want our payments to go through without failing. If you don’t have the balance that you are trying to transfer, your payment will fail and no money will be transferred.
  • MassPay requires you to upload a file containing the information of your payees in order to make payments. The file should include the amount that needs to go to that payee, their email address and the currency that you are paying in. The downside of this is that there isn’t a nice web interface you can enter this information into, you have to work with a text document. The upside is that you can pay as many contractors as you want to with that one file, so if you have multiple payees it’s a huge timesaver.
  • The sender pays the fees, not the receiver.
  • MassPay has extremely low fees. You pay per line item (transaction) in text file I mentioned above. If the receiver is in the USA, you pay 2% of the payment, but that 2% is capped at $1. That means if I pay a contractor in America $2,000, we don’t pay $40 in fees (2% X $2,000), we only pay $1. That’s a huge money saver. For international payments, the cap is $20 instead of $1, so it can get a little more expensive. For example, we pay our 14 contractors (both local to USA and international) with MassPay. We recently processed a total payment of $4,355.65 and paid $58 in fees because there were some payments that were more expensive than others. If all the contractors were in the USA, our fees would have only been $14 ($1 per line item). Now, we could save a bit of money by changing our payment schedule to once per month to take advantage of the caps, but we think the fees are worth getting the money to our contractors sooner.

2. PayPal Web Payments – This is the traditional way of using PayPal. You enter the payees one-by-one into a web interface and process the payment. Here are the main points that define PayPal web payments:

  • Payment is made through PayPal web interface.
  • Payees need to be entered one-by-one.
  • You don’t need to maintain a balance in PayPal, it will deduct the money from your bank account or credit card automatically if you don’t have a current balance.
  • Payee pays the fees.
  • Fees are 2.9% + $0.30 per transaction in the US, and 3.9% + exchange fee for international payments.

Below is a section of Hubstaff’s income statement for June 2015, taken from our accounting software. As you can see, we spent $27,637.43 for our contractors. You can see more of our numbers live at Baremetrics; Hubstaff is a completely transparent company.

I’ll be sharing the exact method that we use to automate our payroll further in the article, but first let’s go through a brief summary of other contractor payment options.

Option 2: Traditional Payroll Services

I used these services for years and had traditional employees. We used a service called Paychex that got the job done. Their cost structure is something like $50 a month per employee, which isn’t bad because they take care of all your tax filings, Form 941 and other tax forms required. ADP is the largest of these solutions.

Currently some of the hottest startups operate in this space. Justworks and Zenpayroll are a few popular options. The reason is because this is a large pain point and services like Paychex are behind in technology.

The downside is when it comes to international transactions, most of these services have no clue how to pay independent contractors and employees overseas. Here’s Zenpayroll’s answer for how to handle international contractors – In short, they don’t handle international contractors and they don’t seem to have any plans of doing so. For a company like ours with 9 out 16 contractors being international, this just doesn’t work.

Option 3: Accounting Software (Xero or Quickbooks)

With Xero, I can accomplish in 30 minutes what used to take me around 4 to 5 hours. As someone who values time above all else, Xero gets my highest recommendation. Most of these type of accounting software have online payroll features built in, usually with some integration for ADP’s payroll service.

Quickbooks also has many advantages, many people love it and if you’re one of them you can take advantage of the Hubstaff + Quickbooks integration.

Option 4: Freelance Marketplaces (Upwork, Odesk, Elance, Freelancer)

Pros – The first obvious choice to pay contractors is to go through a freelance marketplace like Upwork. They make it really easy to pay contractors because they allow you to charge payroll to your credit card and transfer the money to your contractors. They also keep necessary reports for taxes and support weekly budgets.

Cons – The downside to using Upwork is that they take 5 % – 20% of payroll. For a company like ours, that’s just too much. It would be $2,700 a month ($32,400 annual) just in fees. Yep, you read that right… By using the Hubstaff + Paypal integration, we save $32,400 for the bottom line of our company.

Handle Online Payroll with Hubstaff and PayPal

Free for 14 Days

A common misconception when outsourcing is that Upwork is free and that the contractor is the one paying the fees. Here’s why that thinking is incorrect; freelancers know that Upwork will take a percentage, so they can (and probably should) raise their hourly rate to offset this payment and send the cost back to the employer.

Freelancer marketplaces also often have set payment schedules, which can get inconvenient if you want to pay contractors on your own timetable.

Perhaps the biggest problem with freelance marketplaces are alignment issues. Freelancers are paid when they track time in their tracker, so they have an incentive to keep that time tracker rolling unchecked by idle time warnings. Keeping their timers running without remote employee monitoring tools can also make freelancers look more active, even if they aren’t doing any work. So, if an employer notices mediocre work taking up hours of time, they can get suspicious and potentially reduce the budget, which will also lower the revenue the marketplace makes. It’s a complicated cycle that we’d prefer to avoid.

How We Use Hubstaff to Pay Our Team

We use our own service, Hubstaff, to pay our contractors. Why? It’s cheap, it’s automatic, it’s pinpoint accurate, and we invested a lot to build it well. We built Hubstaff specifically to pay contractors overseas and solve the pain point of limited or flawed online payroll options. There are two ways to pay your team in Hubstaff.

Hubstaff for payroll is cheap, automatic, pinpoint accurate and effective. Click To Tweet

Method 1 – Manual Team Payments

The manual payment option allows you to go into Hubstaff, mark team members as “paid” and then process the payment in your chosen platform. All you have to do is set the rate for a contractor, the date range you’re paying for and hit “Make Payment” on the bottom right of the screen.

After you mark these users as “paid” for that date range you’ll actually have to go and process the payment. This can be done through the regular PayPal web payments option above, MassPay or any other system that you want to use. Once you process the payment and mark your team as paid, you can export the payment for Paypal MassPay, Payoneer, Excel, or Quickbooks. Here’s how it looks:

Hubstaff will also keep the reports for your records, so you can come back to view the payment, payment dates, who made the payment and the amounts. Here’s how that looks (notice you can also get back to the export screen from here):

The Hubstaff manual payments option is the most flexible option that we provide. Here are the highlights of the Hubstaff’s manual team payments:

  • You can use any system you want to use.
  • If you have a pay rate set for the user, we will keep track of the amount you owe them. We also keep track of the amount that you’ve paid them.
  • If you are using the regular PayPal web payments option, Paypal will send the payment to your contractor and you are not required to maintain a balance in Paypal. It will draw from your credit card or your bank account.

Method 2 – Automatic Payroll

For the automatic version, we currently have two supported payment options; Paypal MassPay and Payoneer. Both require you to maintain a larger balance in your account than the payments you send out.

With Hubstaff’s automatic payroll option, payments will be processed without any work required on your part. The first step is to connect Hubstaff to your payment account.


Then set up each contractor with his or her own specific payment settings.


The options you can set are:

  • Payment Method: Automatic or Manual
  • Pay Period: Weekly, Twice per month, Bi-Weekly, or Monthly
  • Rate Type: Hourly or Fixed
  • Pay Rate: Open to whatever hourly rate you agree on

Once all your users are set up on the automatic payroll system, you’ll see a page that looks like this:

This page shows you the settings for each of your contractors.

Automating your payroll will save time and energy that you can use to grow your business. Click To Tweet

Once this is set up, Hubstaff will process the payments automatically on the schedule that you have set for each contractor. You can access a record of your payments in Hubstaff just like with the manual method, the only difference is that the Method will show as “Automatic.”

We have a complete Automatic Payroll support document on our support site so you can learn more about the system.

Automate Payroll with Hubstaff

Free for 14 Days

What about Taxes?

Since all of our people are hourly contractors with other clients we send them 1099s. I run a simple report in Hubstaff or Xero that shows me how much money I paid them for the year. I only do this once a year and it doesn’t take more than 30 minutes of work to run all the reports and process my team’s 1099s.

One of our secrets is that we use a service called Greatland, which will send your contractors a physical copy of their 1099, store a digital record for you and file a copy with the FED for only $5.95 per contractor. All you need to do is have a system that keeps track of how much you paid each contractor for the year, plug that number into Greatland and hit submit.

This convenience is great for us and the service is important to our business because it’s important to stay on top of your taxes, even if you are a remote worker. There is no accountant needed for this process, but an accountant can also do this for you pretty cheap (usually around $100 USD per contractor).

Since we are based in the United States, we only have to send 1099s to US based contractors. We don’t file anything for the majority of our international team.

Hubstaff time tracking
  • Great post! Glad to be a part of Hubstaff. So my questions: Let’s say my outsourcing team lives in Pakistan. Do they have to have Pakistan based paypal accounts to receive money OR they can still receive payments to their bank accounts. The reason I ask this question is because there is no Paypal Mastercards avail in Pakistan to use paypal balance and Standard Chartered Bank charges them a fee to transfer from Paypal to bank account (as I was told).

    • Hi Konstantin, we’ve never had a problem paying people in Pakistan via our regular paypal account that is based in the US. We don’t use the payoneer mastercard option, but we have in the past and it seemed to work fine, but the downside is that I don’t think the contractors liked it as much because it was not as liquid of a currency for them obviously. I believe that Pakistan contractors can use their paypal balances to transfer money to their bank accounts but there may be some limiting factors such as amounts they can move at one time, etc..

  • How do you pay your contractor in India? PayPal won’t touch it. We only have one team member in India but the time and money spent trying to pay her is ridiculous!

    • Hi Susan, we actually pay several contractors in India via Paypal without any problem. Fees are a little higher as they are with any international country but we’ve always been able to get payments to India without problem. I’ll get someone on my team to comment here – maybe he can help.

      • Hey @disqus_ExQHhoXuK3:disqus , I’m one of the team members from India working at Hubstaff. When I started out, even I thought that the Paypal fees was bit of a problem. Paypal used to cut ~4.5% from the amount I used to receive which was not cool.

        So to solve that, we setup mass payments in Paypal (via Hubstaff) and it has worked out quite nicely for us. Now no fees is cut from the amount I receive & the company only pays a small fee (1%) to Paypal for transferring the money to me. Best part of all this? It’s completely automated using our app. I clock my hours and I get paid immediately after the week ends (my pay period is setup weekly but you can setup monthly also if you want). Here are a few links that may help you:

        1. To setup automatic payroll on Hubstaff –

        2. To enable the user for Payroll on Hubstaff –

        Hope this helps! Let me know if you have any questions and I’d be happy to answer them for you.

      • I would really appreciate that. I can’t find the page in the PayPal website that says they do not transfer money into India, but I did notice that India is not an option on the price estimator tool country list. I’ve even called PayPal and was told they do not send money from US to India. I’m not sure what I am doing wrong but i sure would appreciate any insight you have! 🙂

      • Please do – it is quite a challenge for us. PayPal will not send payment from the US to India. What’s your secret?

  • unc0nnected

    Fantastic post!