How Freelancers are Hired at

Osmosis Support posted this on hiring

The following is an interview with the founder of, detailing how we approach hiring freelancers for contract work on our CRM for proposals and questionnaires. We hope this helps freelancers by providing a window into how a startup approaches hiring out work for small projects.


What kinds of projects do you hire out?

I’ve hired out a few things - writing projects as part of an SEO campaign, projects for small product features, and worked with an offshore team that did extensive product updates.


How do you decide which projects to hire out?

I hire out small projects for writing and product integrations. These are chosen based on how easily the worked can be carved out - it is best if the work product is very well-defined, so that people know what “done” and “working” means.

I do also have a writer on retainer - this is a role that will likely grow over time as she gets a deeper understanding of the product.


Where do you find freelancers?

I’ve hired people through eLance, but it’s a last resort - I much prefer someone I’ve worked with previously, and who I can call if need be. For writing gigs I prefer WritersAccess, as the quality has been much higher than any other site where I’ve seen equivalent services.


What do you look for when hiring?

This depends on two things, the price of the offering and the scale of the project.

The smaller the project is, the more important it is that the person you’re hiring has experience with the work you’re doing. So for instance on elance, you find a lot of offshore firms that are cheap, but have no experience with what they are bidding on. If I was going to hire out a project to do a Quickbooks integration for Osmosis, some familiarity with the Quickbooks API is a big win.

Price is also a factor. It’s a lot cheaper to hire out writers than software developers, and it’s easier to bring someone on and try them out. I’ve been really happy with Writers Access, because I can write up descriptions for a couple dozen blog posts and get as many people to do the work. That gives you an idea what the biggest problems with your own instructions are, and it works well as a good substitute for an interview. Blog posts are cheap enough that if a couple people don’t work out you haven’t really lost anything, so it make it easy to find a few people who are good.


How do you approach distributing work to freelancers?

For written materials, I have set instructions and guidelines. For instance I have documents built into the Osmosis product (sample client intake forms and sample proposals), and we provide a freelancer with reference links for the topic, the title of the document, and a template of what the resulting document should look like.

Software projects are harder to outsource, and harder to evaluate when the work comes back. The software development I’ve outsourced with Osmosis is integrations, which I chose because I can hand out similar documentation to each freelancer, and lets us avoid becoming experts in a bunch of different APIs.

In this case we provide some sample JSON data and C# objects that correspond to this, then written English requirements for what scenarios the integration should handle. Things like “If the client referenced in the invoice doesn’t exist in Quickbooks, the integration code should create it.”


How do you evaluate the work you receive from freelancers?

For writing this is pretty easy, because I’m looking for coherently written text. With someone new I typically take sections of the text they provide and Google for it to make sure they haven’t plagiarized similar documents, but otherwise it’s just like editing any writing. I have one person who has access to post materials, and in that case I occasionally check her work to make sure she’s added basic HTML styling (headers, alt tags and so on), and that the tone is generally on point. That is as much for her benefit as mine, so that she can work confidently knowing she’s going in the right direction.

For software integrations I keep a sandbox of the application where I can put their code, which might occasionally show me a use case they missed, as I can run through more customer cases. It also guarantees that I can run their code to completion, and that I know how to configure the API endpoints for whatever product they are working against. Since I have a background as a software developer, I also do informal code reviews to inspect their work.


How do you decide how much to spend?

We budget for projects based on past revenue. Typically what I’ll do is to solicit bids, and if the only qualified bids are higher than our budget, we don’t do it, or change the scope of the project.


What is the biggest pain point contracting out work?

The biggest problems I’ve had are all around communication. When you’re giving work to a freelancer, it can be tough to communicate the vision for what needs to be done verbally or in written instructions. I’ve had better success with writing detailed instructions on what I need, but it’s exhausting and I’ve run across some people who will ignore your instructions anyway.

On the other side of it, if someone is working on something over a long period of time, I need a way to know where they are at. In an office environment different aspects of this are handled through status meetings and one on ones. I typically ask freelancers to report back to me where they are at, where they are stuck, and what their next task is, but I’ve found a lot of the cheaper freelancers don’t understand the value of this. I’m much more comfortable if I know that some progress is happening.

I think status reports give a freelancer an opportunity to sell me on what they’ve done, although few people take advantage of that. If I’m lukewarm on someone I won’t hire them again. If someone does good work I’m thrilled if I can hire someone again, because it saves me the worry that I have to hire someone again who won’t understand the work they need to do.

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