Hiring Contractors

Our company is looking to expand and hire 20 to 30 new contractors, all 1099, work at home people for various task.

Would rather not deal with the overhead of tax handling and filing, keeping track of employees, etc but absolutely need to stay compliant.

Would you suggest using upwork.com to handle new contractors, payments, etc or some third party service to help best track and pay people? Compliance is key but also want to give people the comfort in knowing they are getting people. Open to feedback.

Thank you.

 

I personally think you're on the right track. Upwork can streamline the process and help connect you to a larger pool of talent.

I only have experience with it as a writer though and have never used it for outsourcing. My experience as a service provider was positive, though. I no longer do that and have closed up shop, but it was a good experience.

 

If this is a legit business you'll 100% want to take some legal advice in regards to doing that.

Generally if you are going to do this long term with the same people you may run into issues.

Upwork isn't bad, I've also used Hubstaff, which gives a decent way to track the users and also make payments etc. In the end I've restored to doing manual reviews of work every month to make sure everything is ticking a long. It takes a full day to do it, but honestly long term its worth it. One problem with contractors is churn, you'll get some bad people you'll need to replace and its hard to keep hold of the good people unless you take a personal interest in them.

 

You could hire me and I can get you all the resources and flex hours and time as needed.